75 Biggest Fails in NBA History

Michael CahillCorrespondent IFebruary 16, 2011

75 Biggest Fails in NBA History

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    NEW YORK - MARCH 08:  Head coach Isiah Thomas of the New York Knicks watches from the sideline against the Portland Trail Blazers at Madison Square Garden March 8, 2008 in New York City. NOTE TO USER: User expressly acknowledges and agrees that, by downlo
    Nick Laham/Getty Images

    From marketing Michael Jordan to global expansion to the Dream Team to the NBA-ABA merger, there is plenty that the NBA has gotten right. But it seems that with every NBA success there is another, and sometimes more glaring, failure for the league and it’s players.

    Being a hugely visible company, the NBA is susceptible to mistakes and failures both on and off the court. Players, just like coaches, owners, marketers and referees, all make mistakes. Some of the things that go wrong in the NBA go unnoticed, others are no one's fault, and some move beyond the realm of ordinary mistake and move into the realm of classic fail. So here is a look at the NBA’s all-time biggest fails. 

75. Lil Penny

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    Who doesn’t love puppets with Chris Rock's annoying voice? 

    I'm not saying I was happy when Penny got injured. I never want to see a player get injured. But that doesn't mean that I wasn't thinking: "I bet they'll have less of those Lil' Penny commercials."

    I know...I'm a bad person. 

74. Dennis Hopson

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    LOS ANGELES - 1990:  Dennis Hopson #2 of the New Jersey Nets stretches before the NBA game against the Los Angeles Lakers at the Great Western Forum in Los Angeles, California in 1990. NOTE TO USER: User expressly acknowledges and agrees that, by download
    Ken Levine/Getty Images

    The Nets decided to use their third pick in the 1987 draft on Dennis Hopson, passing on Kenny Smith, Reggie Miller and Scottie Pippen. Hopson played five seasons and was often injured during that time. 

73. NBA Players Rapping

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    When was the last time you saw Jay-Z, Eminem or Kanye West making themselves eligible for the NBA draft?

    Rappers should stick to rapping and basketball players should stick to playing basketball. Otherwise you get gems like this.

72. Allen Iverson as a Nugget

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    DENVER - APRIL 28:  Allen Iverson #3 of the Denver Nuggets awaits a free throw against the Los Angeles Lakers in Game Four of the Western Conference Quarterfinals during the 2008 NBA Playoffs at the Pepsi Center on April 28, 2008 in Denver, Colorado. The
    Doug Pensinger/Getty Images

    Iverson has had the nickname "The Answer” for years.

    He was shipped to Denver in 2006 to be the answer and to make the Denver Nuggets an elite team. What it proved was what Iverson had proven for years: that he wasn’t often an necessary ingredient to a winning formula.

    By December 2008, Iverson was shipped out of Denver which started the end of his NBA career. 

71. 1-1-1-1-1-1-1 Format 1956

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    It only lasted for the 1956 NBA Finals, but just the thought that someone wanted to try trading games for a seven-game series is laughable. It doesn't make any sense now (even with teams having private jets) and it sure didn't make sense then. 

70. Gheorghe Muresan In My Giant

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    A terrible basketball player stars in a terrible movie with Billy Crystal. How could that fail?

69. Shawn Bradley

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    Bradley was drafted second overall by the Philadelphia 76ers.

    In his 11 NBA seasons, the promising star ended up averaging eight rebounds, six points and two blocks a game. Those totals amount to a fail that the 76ers would like to forget. 

68. Flopping

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    The NBA is all about drawing the foul and to that extent there is nothing better than a good flop. Players have taken flopping to the next degree, with NBA greats like Paul Pierce turning a routine screen into an Oscar-winning performance. The sad thing is that unless they start handing out technical fouls for flopping (which, as obvious as it seems, is hard to prove) the flops will continue. 

    Now a look at Pau Gasol, "The King of Flop." 

67. Three-Point Foul Worth Two Free Throws

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    It’s simple right? You try for a three-point basket and if you are fouled you get three shots. That’s fair?

    That wasn't always the rule. The rule was changed after Game 3 of the 1994 NBA Finals. With the Knicks trailing by three, John Starks attempted a three but was fouled by Hakeem Olajuwon in the closing seconds. The rule stipulated that Starks only got two foul shots. Starks stepped up and made both, but the Knicks ended up losing the game. 

    The unfairness of this rule was so obvious that the fact that it had to be changed at all was laughable. 

66. NBA Stars In Movies

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    With the exception of 'He Got Game' and and Kareem’s role in 'Airplane!', here are a list of the movies NBA players have been in:

    Like Mike

    My Giant

    Blue Chips

    Freddy Got Fingered

    Kazaam

    Good Burger

    Juwanna Mann

    Space Jam

    I’ll stop there. No need to torture you further.

65. The Dunk Contest Since 2000

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    There have been moments or years (mostly in the past) when the Slam Dunk Contest has been relevant, but there were plenty of times when the Slam Dunk Contest has seemed a waste of time. No year was more evident than the 2010 Slam Dunk Contest.

    When you have Nate Robinson and Shannon Brown as your top contestants, and big stars are refusing to participate, then you have to consider whether or not it’s even worth it. For the last decade, the Slam Dunk Contest has been nothing short of failing.

64. Changing the First Round to 7 Games

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    Here’s an idea that didn’t need improving upon. The NBA thought it would be a good idea to take the first round of the NBA playoffs, already a nice-and-tidy five-game series, and extend it two games. The idea was it would prevent the one seed from losing a shorter series, except the Dallas Mavericks ruined that by losing to the eighth-seeded Golden State Warriors.

    So all the NBA effectively did was drag what was already a marathon playoff season out by two more games. That’s good thinking.  

63. Rudy Tomjanovich As Lakers Head Coach

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    DENVER - JANUARY 12:  Kobe Bryant #8 of the Los Angeles Lakers walks back onto the court with head coach Rudy Tomjanovich behind him during the first half against the Denver Nuggets on January 12, 2005 at the Pepsi Center in Denver, Colorado. NOTE TO USER
    Brian Bahr/Getty Images

    After Phil Jackson left the Lakers in 2003, they knew they needed a top-of-the-line coach for Kobe Bryant and company. What they got was two-time NBA champion head coach Rudy Tomjanovich. However, after a disappointing 41 games, Tomjanovich resigned due to health problems.

62. Magic Johnson as a Color Commentator

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    Few things were funnier, or more tragic, than Magic Johnson as the third guy in the broadcast booth. His entire approach to the game was to replay to the audience at home what the players must have been thinking during the previous play. It wasn’t insightful as much as it was playful and painful to listen to.

61. Sidney Lowe Head Coaching

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    During his two stints as an NBA head coach, Lowe managed a 79-228 record. He managed to win 25 percent of his games. During his time as the head coach of NC State, Lowe has barely managed a record over .500.

    A good coach is a good coach. Sidney Lowe is not a good coach. 

60. Rodman’s Hair

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    The NBA’s pound-for-pound best rebounder of all-time is also credited for having the worst hair of all-time. Somewhere in the career of Dennis Rodman, he snapped and thought that looking like a clown made a whole lot of sense.

    More publicized was his hair than his basketball IQ, which was off the charts if anyone bothered to pay attention.  Rodman’s hair got in the way of a lot, including good taste. 

59. Spike Lee Having Courtside Seats

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    There is no bigger annoyance than watching Spike Lee jaw with the NBA greats. While it’s made for some memorable moments with stars like Reggie Miller and Michael Jordan, it’s an act that is tired and played out.  Here’s hoping Spike upgrades to a luxury suite one day. 

58. Ron Artest Down Rodeo

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    Ron Artest plus an Indy Race Car plus Rodeo Drive equals the image that the NBA is not only crazy, but a little dangerous. Good job, Ron Artest. 

57. Houston Rockets Trio

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    We shall call this the Barkley Era in Houston. When Charles signed on with the Rockets, they were repeat champs and looking for a third. With Hakeem Olajuwon and Clyde Drexler already in the mix, Houston looked like the team to beat. However, they failed to make the NBA Finals once with that impressive trio.

    After Drexler retired and Pippen joined the squad, it seemed as if hope had been restored to Houston, but after another failed season Pippen was shipped out to Portland and Barkley was still left without a ring. 

56. Billy Donovan As Magic Head Coach

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    The Magic thought they were getting a steal by hiring two-time national champion head coach Billy Donovan, but what they got was the shortest-lived jump to the pros by a college coach.

    Donovan, then the Florida Gators head coach, jumped to the NBA and signed a contract on June 1, 2007 to be the Magic coach for five seasons. By the next day he was having second thoughts and by June 6, 2007, he had been released from the deal on the condition he didn’t try coaching in the NBA ever again. 

55. Kazaam

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    Welcome to the biggest fail in NBA movie history. While Space Jam certainly wasn’t a great movie, nothing tops the failure that was Shaq’s big-budget movie Kazaam. Not convinced? I’ll give you a taste.

    The movie is about a boy from the “hood” who is lonely and escapes from local bullies and stumbles upon a boom-box that releases a 7'0", 300-pound genie who grants him three wishes.

    It’s currently No. 92 on IMDB’s Bottom 100. 

54. Sloan and Others Without a Ring

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    ATLANTA - NOVEMBER 12:  Head coach Jerry Sloan of the Utah Jazz against the Atlanta Hawks at Philips Arena on November 12, 2010 in Atlanta, Georgia.  NOTE TO USER: User expressly acknowledges and agrees that, by downloading and/or using this Photograph, U
    Kevin C. Cox/Getty Images

    The top three winningest coaches of all-time, Don Nelson, Jerry Sloan and Lenny Wilkens, have but one ring between the three of them. It’s hard to call their combined win total of 3,900 wins a failure, but when you consider that the next two on that list, Phil Jackson and Pat Riley, have 16 rings between the two of them, the idea of failure comes to mind. 

53. Rodman Not in the Hall of Fame

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    17 May 1998:  Dennis Rodman #91 of the Chicago Bulls during the NBA Eastern Conference Finals at the United Center in Chicago, Illinois.  The Jazz defeated the Lakers 112-77. Mandatory Credit: Jonathan Daniel  /Allsport
    Jonathan Daniel/Getty Images

    On a point made earlier, perhaps Rodman’s antics got in the way of just how good he was on the court. Still, to not have the greatest rebounder in history and one of the game's best defensive players in history not in the Hall of Fame is a travesty.

    Perhaps, this year he’ll get in. If not they need to re-examine the entire selection process.

52. Chris Washburn

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    The Warriors select Washburn No. 3 overall in the 1986 NBA Draft. He ended up scoring 222 NBA points before being booted off the Warriors and out of the league. His alleged drug problems and his lack of work ethic made him a questionable pick from the start. It’s a wonder why the Warriors picked him up at all. 

51. Tony Parker Sleeping With Brent Barry’s Wife (allegedly)

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    SAN ANTONIO - JUNE 9:  Tony Parker #9 walks off the court with teammate Brent Barry #17 of the San Antonio Spurs after defeating the Detroit Pistons in Game one of the 2005 NBA Finals at SBC Center on June 9, 2005 in San Antonio, Texas.  The Spurs defeate
    Ronald Martinez/Getty Images

    It’s one thing to be a bad teammate. It’s another thing to sleep with your teammate's wife (allegedly). It’s yet another thing to cheat on Eva Longoria (allegedly). Add that all together and you have one colossal fail by Tony Parker. 

50. Jim Mcllvaine-Shawn Kemp Ordeal

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    11 Nov 1996:  Jim McIlvaine of the Seattle Supersonics runs up the court during their 110-94 victory over the Sacramento Kings at Arco Arena in Sacramento, California. Mandatory Credit: Otto Greule/Allsport
    Otto Greule Jr/Getty Images

    At some point the Seattle Supersonics thought it would be a good idea to take care of Jim Mcllvaine instead of their superstar, Shawn Kemp. Mcllvaine got a seven-year deal and ticked off Kemp until he was dealt out of Seattle.

    During his time as a Supersonic, Mcllvaine averaged about three points a game…if we’re being generous.

49. Stupid NBA Nicknames

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    14 Aug 1994: JOE DUMARS OF THE DREAM TEAM II DEFEATS RUSSIA 137-91 IN THE WORLD CHAMPIONSHIP FINAL AT THE SKYDOME STADIUM IN TORONTO, ONTARIO, CANADA.
    Doug Pensinger/Getty Images

    Rather than drone on and on I’ll leave it at this.

    Joe Dumars: Joe D

    Vince Carter: Air Canada

    Darryl Dawkins: Chocolate Thunder

    Shawn Marion: The Matrix

    Barney Sedran: Mighty Mite

48. Michael Olowokandi

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    BOSTON - NOVEMBER 15:  Michael Olowokandi #41 of the Boston Celtics looks on against the Indiana Pacers on November 15, 2006 at the TD Banknorth Garden in Boston, Massachusetts. The Celtics defeated the Pacers 114-88. NOTE TO USER: User expressly acknowle
    Elsa/Getty Images

    In 1998, the Clippers tried to make the best pick they could. But like most Clippers moves, it ended up being a disaster.

    Instead of picking up Paul Pierce, Dirk Nowitzki, Rashard Lewis, Vince Carter or Mike Bibby, the Clippers picked up the underwhelming Michael Olowokandi. He barely managed double-digit points in his career and never over nine rebounds a game. 

47. Dirk Nowitzki's Mavericks Lose To The Warriors

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    DALLAS - JANUARY: Forward Dirk Nowitzki #41 of the Dallas Mavericks moves the ball against Stephen Jackson #1 of the Golden State Warriors on January 28, 2008 at American Airlines Center in Dallas, Texas. NOTE TO USER: User expressly acknowledges and agre
    Ronald Martinez/Getty Images

    The first-round seven-game series was supposed to be designed so that top seeds like the Dallas Mavericks didn’t go out to the eighth-seeded Golden State Warriors. However, in the 2006-07 playoffs, the Mavericks faced the one team they didn’t want to see.

    The Mavericks dominated everyone that year, but they couldn’t figure out Golden State. Dirk Nowitzki was the MVP that season, but couldn’t propel his team past the team that almost didn’t make it in. 

46. Short Shorts

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    They say that a picture is worth a thousand words.

    So I’ll just stop talking now.

45. Grant Hill

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    PHOENIX, AZ - FEBRUARY 13:  Grant Hill #33 of the Phoenix Suns reacts to a non foul call during the NBA game against the Sacramento Kings at US Airways Center on February 13, 2011 in Phoenix, Arizona. The Kings defeated the Suns 113-108.  NOTE TO USER: Us
    Christian Petersen/Getty Images

    There are few things that bring more sadness to an NBA fan than talking about the career of Grant Hill. While it’s not his fault he had enough injuries to derail anyone’s career, the fact that he had Hall of Fame potential and could never quite achieve it is an utter failure, if not a tragedy. 

44. Failed Sneakers

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    Remember when Fila was the hottest sneaker on the market? No?  Neither does anyone else.

    In the early 1990s, FILA attempted to get into the NBA shoe business to go against Reebok and Nike. What ended up happening was that they didn’t come close to taking a fair share of the market.

    The same thing happened when Ben Wallace and Stephon Marbury decided to join forces with the now-defunct Steve & Barrry’s. The result was a shoe that was incredibly cheap made by a company that was incredibly broke. 

43. Shawn Kemp

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    12 Dec 2000:  Shawn Kemp #40 of the Portland Trail Blazers looks to move the ball during the game against the Golden State Warriors at The Arena of Oakland in California. The Trail Blazers defeated the Warriors 101-92. NOTE TO USER: It is expressly unders
    Jed Jacobsohn/Getty Images

    There should be a handbook that Shawn Kemp hands out to rookies about how to not ruin your career. At the height of his career, Kemp did everything a star player shouldn’t do.

    Got mad about money.

    Demanded a trade.

    Got fat.

    Got into trouble off the court.

    Wasted golden opportunities to get back into the league.

    That is pretty much the guidebook for all NBA players to follow.

42. Shaq to Phoenix

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    OAKLAND, CA - MARCH 15:  Shaquille O'Neal #32 of the Phoenix Suns dribbles the ball against the Golden State Warriors during an NBA game on March 15, 2009 at Oracle Arena in Oakland, California. NOTE TO USER: User expressly acknowledges and agrees that, b
    Jed Jacobsohn/Getty Images

    The Phoenix Suns had a lot of trouble making it to the NBA Finals even with one of the most talented rosters in the league. They couldn’t find a way to beat the defensive-minded, low-post team, the San Antonio Spurs. So the Suns, looking to make a dramatic change, brought in Shaquille O’Neal.

    The result was a disaster. Shaq never quite fit in with the Suns open-floor play. He was a non-factor when they did get to the Spurs and he proved that his days as a dominant center were long behind him. 

41. Birdman in the Dunk Contest

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    Chris Andersen is not known for his dunking prowess. He’s better known for his outrageous appearance. So there were questions about how well he’d do in the dunk contest. The results, as the video shows, were evident. 

40. Juwan Howard’s Contract

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    This is not an attempt to smear what has been a very proud NBA career, but his contract of seven years and $100 million was nothing short of stupid. In his time as a Wizard he averaged 18 points and led the Wizards to the playoffs once and made the All-Star team once. The Wizards learned to never give that kind of contract out again...

    (Enter Gilbert Arenas)

39. Vin Baker

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    Talk about a career wasted. After Vin had made his fourth All-Star appearance, the Bucks decided to reward him with a seven-year contract for over $86 million. Vin repaid the favor by becoming an utter disappointment due to a severe alcohol problem that pushed him right out of basketball. 

38. Len Bias

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    His shot at the NBA was a failed attempt as he tragically died of a drug overdose the day after he was drafted by the Boston Celtics. His career, and the future of the Boston Celtics for years, would all fail on that same day. 

37. The Warriors Trade For Joe Barry Carroll

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    The Golden State Warriors got Joe Barry Carroll and Ricky Brown in 1980. All they had to do was give up Robert Parish and the third overall pick. The Celtics used that to get Kevin McHale.

    Fair trade right? 

36. The Three-Point Line

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    Of course the three-point shot itself is a success. However, the fact that it was around since 1945 and not adopted by the NBA until the 1979-80 season is a colossal fail, especially given its incredible success as part of the game. 

35. Drafting Size First

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    CHICAGO - NOVEMBER 01: Greg Oden #52 of the Portland Trail Blazers watches from the bench as his teammates take on the Chicago Bulls at the United Center on November 1, 2010 in Chicago, Illinois. The Bulls defeated the Trail Blazers 110-98. NOTE TO USER:
    Jonathan Daniel/Getty Images

    The NBA Draft has been littered with stupid selections, but the dumbest thing the draft has done is establish the idea that you must draft size over all. This has produced Greg Oden and Sam Bowie just for starters. The draft should be about acquiring the best talent. Drafting for size is a dumb reason to draft a player. 

34. John Starks Going 0-10

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    21 FEB 1995:  JOHN STARKS OF THE NEW YORK KNICKS CHARGES FOR THE BASKET AGAINST THE CLEVELAND CAVALIERS DURING THE FIRST HALF THEIR CLASH AT MADISON SQUARE GARDEN, NEW YORK. Mandatory Credit: Doug Pensinger/ALLSPORT
    Doug Pensinger/Getty Images

    When the Houston Rockets and New York Knicks went seven games deep in the 1994 NBA Finals, Starks was supposed to show up big. However, Starks barely showed up at all. He ended up with a 2-for-18 shooting performance and a 0-for-10 fourth quarter. He was supposed to be their clutch performer, but when it really counted he went ice cold.

33. Nick Anderson's Free Throws

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    Everyone knows that the first game of any series is important. So when the Magic were up by three points in Game 1 of the NBA Finals against the Houston Rockets, the task became really easy for Magic guard Nick Anderson.

    Sink your free throws.

    Anderson didn’t. He missed four free throws. The Rockets were able to tie it and put in into overtime. The Magic lost it in overtime and were swept out of the NBA Finals and didn't get back there for over a decade. 

32. Jordan Plays Baseball

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    There are few things in the NBA that were more shocking than watching Jordan retire at the height of his fame and career. He was a three-time champion who was walking away from the game he loved.

    No one ever thought Jordan would leave to play in the MLB, but that’s just what he did. Jordan spent two years playing in the Chicago White Sox minor league organization. He was a great boost for their attendance, but he was never going to make it to the majors. He finally got the itch again and moved back to a sport he could dominate. 

31. One Year of College Rule

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    SPOKANE, WA - MARCH 16:  Kevin Durant #35 of the Texas Longhorns sets up for the foul shot against the New Mexico State Aggies during the first round of the NCAA Men's Basketball Tournament at Spokane Memorial Arena on March 16, 2007 in Spokane, Washingto
    Jonathan Ferrey/Getty Images

    The NBA made the decision, conveniently after LeBron James did it, to make a one-year college rule for all incoming players. A player now must play a year of college hoops or play overseas while waiting for eligibility into the draft.

    What this did was create a culture of one-and-done stars to water down the college game and introduce a group of players who were still pretty raw when they reached the pro level (how much do you really learn in a year?).

30. The Portland Trail Blazers (Jail Blazers)

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    SACRAMENTO, CA - JANUARY 20:  Rasheed Wallace #30 of the Portland Trail Blazers smiles during the game against the Sacramento Kings at Arco Arena on January 20, 2004 in Sacramento, California.  The Trail Blazers won 109-104.  NOTE TO USER: User expressly
    Jed Jacobsohn/Getty Images

    If you want a reason why the NBA started to get the perception of being a “thug” league, look no further than Portland. The Trail Blazers were given the name “The Jail Blazers” during the 2000 to 2003 seasons. Portland GM Bob Whitsitt assembled a group of talented-but-troubled stars that were known more for their off-the-court antics then their on-the-court success.

    The Blazers featured a roster of those who were charged with marijuana possession and a registered sex offender. The result was a lackluster team and a loyal fan base that was starting to turn away. 

29. Eddy Curry

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    CHICAGO - NOVEMBER 04: Eddy Curry of the New York Knicks sits on the bench and watches his teammates take on the Chicago Bulls at the United Center on November 4, 2010 in Chicago, Illinois. NOTE TO USER: User expressly acknowledges and agrees that, by dow
    Jonathan Daniel/Getty Images

    This was a guy who was supposed to usher in a new era for the Chicago Bulls. Drafted fourth overall in the 2001 NBA Draft, Curry has spent the majority of his career as a disappointment. He’s the big man who can’t rebound. This was verified by Bulls coach Scott Skiles who, when asked about what Curry had to do to make himself a better rebounder, said “jump.”

    Curry moved on to New York where his albatross contract has weighed down the Knick’s payroll and his production has been limited due to injuries and a questionable work ethic.

28. The First Five Teams of the 1978 Draft

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    DENVER - 1990:  Boston Celtics forward Larry Bird #33 looks on from the bench during game against the Denver Nuggets at McNichols Arena in Denver, Colorado. (Photo by Allsport  /Allsport
    Getty Images/Getty Images

    Each team that drafted before the Boston Celtics that year had the chance to draft Larry Bird, but didn’t. Bird was going back for his senior season, but there was a rule that you could retain the rights to a player after their junior season.

    The first five teams passed on Bird, but Red Auerbach picked up his rights. There’s a reason Red was a winner. 

27. The 1998 Lockout

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    No sports industry wants a lockout. It’s not good for the fans interests and it isn’t good for the league's interests. So the last thing the league wanted to do was have a lockout at the height of its popularity (anyone seeing an NFL comparison), but the league decided in 1999 to lockout the players until they could get the salary cap under control.

    What happened was the league came back, but it’s biggest draw had disbanded and the casual fans who might have been interested had the season started on time, were now completely tuned out and the NBA has struggled to get them back ever since. 

26. Birth Control

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    14 Nov 2000:  Larry Johnson #2# of the New York Knicks walks out on the court during the game against the Seattle SuperSonics at Key Arena in Seattle, Washington.  The SuperSonics defeated the Knicks 96-75.   NOTE TO USER: It is expressly understood that
    Otto Greule Jr/Getty Images

    There was a time when it seemed that everyone from Shawn Kemp, to Larry Johnson and Scottie Pippen were all being outed for allegedly having children with several different women. You know it’s a problem because right now you are thinking of someone that I didn’t mention. 

25. Kobe Post-Denver

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    Kobe gets an epic fail for doing a few things wrong. The first mistake he made was cheating on his wife at all. The second mistake he made was being in the position to make the mistake he may or may not have made (I’m speaking of the rape allegations).

    The third was throwing his teammate and already mortal enemy, Shaquille O’Neal, under the bus by telling the press that Shaq cheats on his wife. And his fourth mistake was thinking he could make everything better by hooking his wife up with a $4 million ring.

    Those things can’t help your situation or reputation in life. They can only hurt you.

24. Kwame Brown

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    CHARLOTTE, NC - FEBRUARY 11:  Teammates Kris Humphries #43 and Anthony Morrow #22 of the New Jersey Nets try to stop Kwame Brown #54 of the Charlotte Bobcats during their game at Time Warner Cable Arena on February 11, 2011 in Charlotte, North Carolina. N
    Streeter Lecka/Getty Images

    It’s rare when Michael Jordan fails in the world of basketball, but as an executive Michael Jordan only knows failure. His biggest fail was in drafting Kwame Brown. When the Wizards had the No. 1 overall pick in the 2001 draft, under the guidance of Michael Jordan, they drafted Brown.

    To say Brown has been disappointing would be an understatement. Minus a seven-game series in which he shined with the Los Angeles Lakers, Brown has done nothing more than take up a spot on the bench. 

23. The WNBA

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    Let me know if you can name the last team to win a WNBA title (and if they are your city’s team, then it doesn’t count). The WNBA was supposed to bring in the female fans, but all it has done is make people change the channel. 

22. Sprewell Feeding His Family

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    LOS ANGELES - MARCH 31:  Latrell Sprewell #8 of the Minnesota Timberwolves looks on during a break in action against the Los Angeles Lakers on March 31, 2005 at Staples Center in Los Angeles, California. NOTE TO USER: User expressly acknowledges and agree
    Lisa Blumenfeld/Getty Images

    Latrell Sprewell choking PJ Carlesimo was bad enough, but he might be more famous for his contract comments.

    When Sprewell demanded a new contract from the Wolves, threatening that he would not play during the season, he famously said that he could not put himself at risk of getting himself injured for the $14.6 million he was set to make because “he had a family to feed.”

    Middle class men and women working two jobs to make ends meet naturally sympathized with Sprewell. 

21. Jordan Coming out of Retirement

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    PHILADELPHIA - APRIL 16:  Michael Jordan #23 of the Washington Wizards on the court during the final NBA game of his career, played against the Philadelphia 76ers at First Union Center on March 30, 2003 in Philadelphia, Pennsylvania.  The Sixers won 107-8
    Ezra Shaw/Getty Images

    There was no better exit for the game's greatest then when Jordan hit the final shot against Utah in the 1998 NBA Finals. It was his sixth championship and cemented his legacy as the game's greatest Finals performer.

    However, Jordan never knew when enough was enough and two years later he made his comeback to the Washington Wizards. He would go on to play for two seasons in which he put up respectable numbers, but it was like watching that prize fighter go one match too many. He didn’t have the same step and the rest of the league had passed him by. 

20. Drug Use Throughout the 1970s

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    In 1983, the NBA decided to adopt a drug policy. This was a great move, but one that was far too little too late. In the NBA during the 1970s, drug use was rampant (allegedly) on NBA teams and gave the league an unhealthy image. Like most image problems in the NBA, it would take the Association far too long to clean it up. 

19. Expansion to Canada

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    16 Feb 2001:  Mahmoud Abdul-Rauf #1 of the Vancouver Grizzlies runs with the ball during the game against the Golden State Warriors at the Arena in Oakland, California.  The Grizzlies defeated the Warriors 92-79.    NOTE TO USER: It is expressly understoo
    Tom Hauck/Getty Images

    The NBA has considered itself a global company, so it would make sense that they try their brand out in Canada. The results? Not so good. The Vancouver Grizzlies fizzled and are now the Memphis Grizzlies. Meanwhile, the Toronto Raptors had a few good seasons with Chris Bosh, but he too took his talents to South Beach.

    If it doesn’t have ice, Canadians aren’t interested. Why can’t the NBA see that?  

18. Larry Brown As the New York Knicks Coach

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    CHARLOTTE, NC - DECEMBER 21:  Head coach Larry Brown of the Charlotte Bobcats yells to his team during their game against the Oklahoma City Thunder at Time Warner Cable Arena on December 21, 2010 in Charlotte, North Carolina. NOTE TO USER: User expressly
    Streeter Lecka/Getty Images

    Here’s a quiz. What do you get when you put an old-school coach who believes in hard work and defense to achieve success in the NBA, with a team filled with overpaid, underachieving players? That’s right, you get Larry Brown's reign in New York.

    His tenure in New York lasted less than one calendar year.  Brown filled that time feuding with players and the front office. The fail for the Knicks in this regard was signing the nomadic Brown to a five-year, $50 million contract. 

17. The Decision

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    GREENWICH, CT - JULY 08:  (EXCLUSIVE COVERAGE)  LeBron James attends the LeBron James Pre Decision Meet and Greet on July 8, 2010 in Greenwich, Connecticut. Proceeds from tonight's 2.5 million dollar event will be donated to the Boys & Girls Clubs of Amer
    Larry Busacca/Getty Images

    LeBron James had every opportunity to test the free agent market in the 2010 summer. While he fielded offers from several teams, the consensus was that he would pick his hometown team, the Cleveland Cavaliers.

    When LeBron decided to team up with ESPN to reveal his decision on national TV, the thought was it had to be Cleveland because no one would go on national TV and pick the “other woman,” right? Wrong.

    LeBron went on and told Jim Gray that he was taking his talents to South Beach. The backlash, not just from Cleveland but from the NBA fanbase as a whole, was enormous. James went from one of the game’s most beloved to one of the most hated in the span of an hour. So much for no such thing as bad press. 

16. Tim Hardaway Making Anti-Gay Comments

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    NEW YORK - OCTOBER 6:  Former NBA player Tim Hardaway attends The 24th Annual Great Sports Legends Dinner benefiting The Buoniconti Fund to Cure Paralysis (national fundraising arm of The Miami Project to Cure Paralysis) at The Waldorf-Astoria on October
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    Let’s let Hardaway speak for himself. After it came out that former NBA player John Amaechi was homosexual, Dan LeBatard asked Hardaway for his thoughts on his radio show.

    Hardaway was doing well for himself after basketball and staying visible and active through the NBA. Then he said this:

    "Well, you know I hate gay people, so I let it be known. I don't like gay people and I don't like to be around gay people. I am homophobic. I don't like it. It shouldn't be in the world or in the United States. So yeah, I don't like it.''

    Hardaway's career was never the same. 

15. Darko Milicic

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    PHOENIX - DECEMBER 15:  Darko Milicic #31 of the Minnesota Timberwolves during the NBA game against the Phoenix Suns at US Airways Center on December 15, 2010 in Phoenix, Arizona.  The Suns defeated the Timberwolves 128-122.  NOTE TO USER: User expressly
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    You would think that the nickname the “Human Victory Cigar” would be considered a compliment, but not when you are Darko. The man who went second in the 2003 NBA Draft has been nothing short of disappointing in his NBA career.

    During his time in Detroit, he was only brought in when they had an insurmountable lead. Since then he has played for four different teams, but what is most disappointing about Darko’s career is who he was drafted ahead of. Drafted immediately following Darko were Carmelo Anthony, Chris Bosh and Dwyane Wade. Milicic has never been in the same class as those guys. 

14. Dan Gilbert and The 2011 Cleveland Cavaliers

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    CLEVELAND - OCTOBER 27:  Majority owner Dan Gilbert of the Cleveland Cavaliers talks to the media prior to playing the Boston Celtics in the Cavaliers 2010 home opner at Quicken Loans Arena on October 27, 2010 in Cleveland, Ohio.  NOTE TO USER: User expre
    Gregory Shamus/Getty Images

    After LeBron James made his “Decision,” the furious Dan Gilbert, Cleveland's owner, released a statement telling the world that the Cavs would reach and win an NBA Finals before LeBron would.  Most experts picked Cleveland to be a playoff team. After all, they did have the league's best record over the last two seasons.

    However, not only have the Cavs failed to live up to expectations, but they have also failed to be competitive. The Cavs have had a 26-game losing streak and their franchise value has dipped by more than $100 million. 

13. 2000 NBA Draft Class

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    BOSTON - FEBRUARY 27:  Keyon Dooling #55 of the New Jersey Nets takes a shot in the second half against the Boston Celtics at the TD Garden on February 27, 2010 in Boston, Massachusetts. The Nets defeated the Celtics 104-96.  NOTE TO USER: User expressly
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    There is no such thing as a perfect NBA Draft. There will be some busts and bad picks along the way. But every NBA Draft seems to feature at least one solid superstar. That all changed in 2000.

    The 2000 NBA Draft is easily the most underwhelming draft class ever. It’s No. 1 pick was Kenyon Martin and he might be the best player to come out of that draft. That’s not saying much. Players such as Keyon Dooling, Courtney Alexander and Jason Collier populated the draft class and made it a colossal failure. 

12. Seattle Loses The SuperSonics

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    DENVER - MARCH 16:  Kevin Durant #35 of the Seattle SuperSonics controls the ball against the Denver Nuggets at the Pepsi Center on March 16, 2008 in Denver, Colorado. The Nuggets defeated the Sonics 168-116. NOTE TO USER: User expressly acknowledges and
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    Howard Shultz sold the Seattle SuperSonics franchise to Clay Bennett because he thought they would not take the franchise to Oklahoma City right away. Instead he thought they would work with the city in order to get Seattle to help update the stadium.

    What happened was Bennett took the Sonics and it’s WNBA sister and brought them to OKC, leaving Seattle high and dry. 

11. Isiah Thomas As Anything But a Player

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    CHICAGO - JANUARY 08: Head coach Isiah Thomas of the New York Knicks talks with Nate Robinson #4 during a game against the Chicago Bulls on January 8, 2008 at the United Center in Chicago, Illinois. The Knicks defeated the Bulls 105-100. NOTE TO USER: Use
    Jonathan Daniel/Getty Images

    Isiah Thomas was a tremendous player, but when he decided to get into coaching and the front office of basketball, he proved he was just that: a tremendous player. As a head coach for the Indiana Pacers, Thomas failed to make them into anything relevant and after a series of early playoff exits, he was fired and joined the front office of the Knicks.

    While Isiah inherited a bad situation (we’ll get into that in just a bit), he also managed to make matters worse. Thomas traded for a disappointing Eddy Curry. He traded away countless draft picks in rich draft classes, and also sexually harassed a New York Knicks employee. All in a days work for good ole’ Zeke. 

10. 1972-73 Philadelphia 76ers

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    One season. Nine wins. The definition of team failure.

9. Elgin Baylor As Anything But a Player

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    Elgin Baylor must be the model for Isiah Thomas. As a coach for the New Orleans Jazz, Baylor coached them to an 86-135 record. As an executive for the Los Angeles Clippers for 22 seasons, he managed to bring the team just two winning seasons.

    Of course Baylor, because of that stunning front office success, sued the Clippers saying that not only was he fired due to his age and race, but that he was grossly underpaid during his time in Los Angeles. Tell me…how much should a horrible GM get paid?

8. Donald Sterling

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    Not only is Donald Sterling the owner of one of the worst franchises (and I’m being kind when I say “one of”) in all of sports, the Los Angeles Clippers, but he’s also a bad guy. During his time with the Clippers, he has been sued for racism and sexual harassment. He’s been known to heckle his own team and he’s been accused of being a slum lord. He also allegedly asked a former coach to tape up the players before games so he could save on the cost of a team trainer.

    No wonder the Clippers don’t have Donald Sterling Day at the Staples Center. 

7. Scott Layden With The Knicks

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    Before the world continues to blame Isiah Thomas for all the Knicks woes, people need to take a look at the resume of Scott Layden.  He was the GM of the Knicks from 1999-2004.

    During his time he signed Allan Houston to a massive contract. He traded Patrick Ewing for Glen Rice. He traded away draft picks for Othella Harrington and Muggsy Bouges. He traded away Nene Hilario and Marcus Camby for Antonio McDyess.

    To say his time in New York was a fail would be an understatement. 

6. Microfiber Ball

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    During the 2007 season the NBA decided that they were going to introduce a new ball. A microfiber ball was going to replace the leather ball the players had been using their whole lives. The ball was hated universally by the players and they filed a lawsuit with the league. The lawsuit never got to court as the league decided it was time to go back to the leather ball and put it back in play during the start of 2007. 

5. Organizations Win Championships

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    23 Jul 1998: General Manager Jerry Krause at the Chicago Bulls Press Conference at the United Center in Chicago,Illinois. FOR EDITORIAL USE ONLYMandatory Credit: Jonathan Daniel  /Allsport
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    The Chicago Bulls were coming off their second three-peat. The dynasty was still in full swing and Jordan was still the biggest draw in the NBA. Everyone was happy except for Jerry Krause. The often-criticized GM made the declaration that “organizations win championships” and decided to prove it.

    No one would ever doubt that organizations make moves that bring rings, but no GM would ever be stupid enough to test the theory by breaking up a dynasty. The Bulls were in prime position to win another title, especially given the likelihood of a strike-shortened season the next year. Krause refused to re-sign Jackson and signed-and-traded Scottie Pippen. He also forced the retirement of Michael Jordan, the game's single biggest draw.

    Since that time the Bulls have failed to even reach the Eastern Conference Finals and spent several seasons struggling to get to the playoffs. So much for that mantra. 

4. The NBA Lottery

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    The NBA Lottery is a flawed idea. In most sports the worst team gets the best pick the next year. However, in the NBA, one great player can have a drastic effect on a team’s future, so teams began tanking the season in order to land the top draft choice.

    The NBA’s solution? Put a series of ping-pong balls in a big bucket and pick out the draft order of the 14 teams that didn’t make the playoffs. The worse your team does, the more ping-pong balls you get. While this has stopped most teams from tanking, it’s resulted in a very imperfect draft process that most recently saw the Chicago Bulls receive the first overall pick in a year in which they were not close to being the most deserving team for such a pick.

    There may be no perfect fix to the NBA Draft, but something must be better than the lottery. 

3. Portland Drafting Sam Bowie

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    It’s easy not always easy to get a top two pick wrong, but the Portland Trail Blazers make it look easy. No instance was more evident than when they drafted Sam Bowie ahead of Michael Jordan and Charles Barkley in the 1984 draft.

    Certainly Bowie had potential, but it was marred by his leg injuries that halted him from playing the last two years of his college career. There’s a rule in the NBA that you shouldn’t draft a big man with leg problems, and Bowie is the reason for that rule.

    Making matters worse was that Portland management was told by Bob Knight, who had just coached Jordan on the Olympic team, that they should draft Jordan no matter what.  They went with their gut, though, and ended up drafting one of the biggest busts in NBA history and passing up the G.O.A.T.

2. Malice at the Palace

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    To understand the fail of this you have to understand the NBA at the time. In 2004, the year of the incident, the NBA was still working hard to fight the image that the NBA was a thug league. LeBron James, Dwyane Wade and several stars that would change that image had yet to do so.

    On November 19, 2004, the Detroit Pistons and the Indiana Pacers were playing at the Palace at Auburn Hills. A fight broke out late in the fourth quarter between players. A fan foolishly chucked a Diet Coke at Pacers player Ron Artest. His reaction was typical of Artest (to an extent) as he freaked out and charged into the stands to fight the fan (the wrong fan by the way).

    The result was Artest got suspended for the season and the NBA had a black mark on it forever.

1. Tim Donaghy

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    CHARLOTTE, NC - NOVEMBER 18:  Head coach Paul Silas of the Cleveland Cavaliers confers with official Tim Donaghy #21 during an NBA game against the Charlotte Bobcats on November 18, 2004 at the Charlotte Coliseum in Charlotte, North Carolina.  The Cavalie
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    Where do you begin? Donaghy was an official for 13 seasons and was rather well thought of, or not thought of at all, by the NBA and fans. In 2007 it came out that Donaghy had been involved in betting on NBA games.

    The investigation goes much deeper than can be reported here, but what Donaghy did was hurt the integrity of the game. As time went on, Donaghy accused other officials of fixing games and showing bias to certain players. It is clearly the biggest fail in the history of the sport.