5 Worst Decisions of Danny Ainge's Boston Celtics Era

Danny Ainge has been no stranger to criticism since becoming Boston Celtics Executive Director of Basketball Operations in May 2003 (and President in 2008).

Many cite his propensity for trading homegrown stars, like Antoine Walker and Kendrick Perkins. Others blame glaring weaknesses on NBA draft day. But the 6'5” redhead GM, known for his hard-nosed attitude on the court, has carried his days as an executive with the same disregard for his own popularity.

Ainge often makes decisions that draw the ire of Celtics Nation. His days in charge began with the widely-criticized Walker trade, in which Boston netted Raef LaFrentz, Jiri Welsch and Chris Mills.

At the time, 'Toine was the Celtics' undisputed leader, averaging close to 21 points and nine rebounds per game over his seven-year tenure in Boston. Since he was the first real star of the Boston Garden since the Larry Bird era, fans rejected the thought of losing him and trusting in all young players.

It did not help that the C's averaged less than 35 wins per season in Ainge's first four years at the helm. The chatter among Boston sports radio was that Danny's managerial days would be short-lived.

But he redeemed himself with two huge trades prior to the 2007 season, one for Kevin Garnett and one for Ray Allen. The Celtics won 66 games that year, the franchise's most since 1986. Captain Paul Pierce, Garnett and Allen (donned the “Big Three”) took home the 2008 NBA Championship over their storied rivals, the Los Angeles Lakers.

Ainge was named NBA Executive of the Year.

Boston has won the Atlantic Division every year since, but they have only been back to the NBA Finals once, in a losing effort against the Lakers in a 2010 rematch. The Perkins deadline-day trade in 2011 left a semi-permanent bad taste in a wide array of Bostonian mouths, especially considering the fact that injury-plagued Shaquille and Jermaine O'Neal were left to shoulder the load at center.

But the Antoine Walker trade introduced two positives: no more one-on-one hoisting of three-point shots by an inconsistent ball hog and the arrival of guard Delonte West. And the Perkins trade, like it or not, brought Jeff Green to Boston for an expiring contract. Green may have missed all of 2011 with a heart condition, but he's coming on strong now and looks to be the future of the Celtics.

Leaving aside the court of public opinion, Ainge deserves a pass on those two deals. The following slides detail what actually constitutes the five worst decisions of the Danny Ainge era.

Drafting Gerald Green in 2005

Fresh off a division-winning 45-37 record in Ainge's second season as an executive, the Celtics had three total picks to work with in the 2005 NBA Draft. Boston had primary areas of concern at shooting guard and center, as they lacked range and size. At pick No. 18, Ainge selected Gerald Green, an immature small forward with limited range.

At the time, many analysts considered Green an absolute steal in the late teens of the draft, calling him an ideal work in progress. But the athletic youngster never progressed as a shooter and focused instead on getting his dunks on SportsCenter's top plays. Unfortunately, some slam attempts on wide-open transition plays led to highly-embarrassing clangs.

“He was so young,” Coach Doc Rivers said about Green in January of this year. “I don’t know if he wasn’t listening to me or anyone [at] that time. He had a lot going on. [Winning] the dunk contest might have been the worst thing that ever happened to him. It’s just hard for a young guy.”

Ainge grew tired of the "young guy" act after two seasons of Green's failure to fill Boston's voids. He logged only 101 threes and 101 assists before getting packaged to Minnesota in the Garnett trade. Some would call this a "silver lining," but many others recognize that Al Jefferson and Sebastian Telfair were the players who swayed then-GM of the Wolves Kevin McHale. Equal or lesser valued players than Green would have finalized that deal.

Green has since left the NBA to play in Russia, only to make a triumphant return with the 2011-12 New Jersey Nets. He averaged career-highs in points (12.9) and rebounds (3.5) but has come back to Earth this year as an Indiana Pacer.

Still only 27 years of age, Green provides dynamic offensive skills coming off Indiana's bench, and he has matured exponentially. But he was nothing more than an immature, dunk-obsessed bust during his tenure in Boston.

Looking back at the 2005 NBA Draft, Ainge could have grabbed Monta Ellis or Jarrett Jack to add range, or David Lee to satisfy their front-court woes.

Hindsight may be 20/20, but Danny had blurred vision in this particular draft.

The Veteran Point Guard Carousel: Payton, Cassell, Marbury

In fairness, Ainge started his managerial career without a true NBA point guard. So he made a splash in August 2004, trading Chucky Atkins, Chris Mihm and Jumaine Jones to the Los Angeles Lakers for Gary Payton and a 1st round draft pick.

While it seemed justified at the time, in that it brought a veteran floor general to a desperate team, this acquisition marked a series of unfortunate point guard moves.

Less than a year after they acquired him, Boston ultimately traded Payton in a packaged deal to bring Antoine Walker back to Boston. Remarkably, they signed Payton as a free agent a week later.

Regardless of Payton's undeniably-impressive NBA resume, he had no place on a roster that was clearly being rebuilt.

He helped Boston achieve some semblance of an offense, at the same time confusing Celtics Nation as to whether they were trying to compete. Despite being a slightly effective player for the C's compared to his allies, the Glove's era in green was a disappointing time for Ainge.

The same can be said for the abominable decision to bring in Sam Cassell in 2008. Yet another veteran point guard, Cassell played a small part in the C's 2008 Championship and excited fans with his likeability and sheer knowledge of the game.

But going forward, he apparently felt too knowledgeable to pass the ball, largely hogging offensive sets despite a .385 field goal percentage. Sam averaged a career-low 4.2 assists per game in Boston, before being traded to the Sacramento Kings for a 2015 second-round draft pick.

Ten days after the Cassell trade, Ainge signed Stephon “Starbury” Marbury, who had just been waived by the New York Knicks.

"We are very excited to have a player of Stephon's caliber joining our team," Ainge said after the acquisition. "Our entire organization is confident in the belief that Stephon can play an important role in helping us to win another championship."

But Marbury was even more unsuccessful than Cassell as a backup to Rondo. Despite playing for Boston under the veteran's minimum, then $1.3 million, he proved more distracting than accommodating for the often-misguided second string.

The 2010 trade that sent J.R. Giddens, Eddie House, Bill Walker and a 2014 second-round draft pick for Nate Robinson did not help. Nor did Ainge's second attempt at bringing in Delonte West for the 2010-11 season. In reality, the only true point guard of substantial value that Ainge has successfully acquired is Rajon Rondo.

The rest of the carousel has quite unfortunately been a rotating circus act.

Failing to Sign Tyson Chandler in 2011

When David Aldridge first announced on NBATV in November 2011 that Boston was eying center Tyson Chandler, Celtics fans got all warm and fuzzy inside. Chandler, who had just played a crucial role in the Dallas Mavericks' NBA Championship, was the premier big man on the free-agent market at the time.

Of course, that meant stiff competition for the big man, who eventually went to the New York Knicks in a sign-and-trade that involved three teams (and the Knicks waiving of Chauncey Billups as part of an amnesty clause). The 7'1”, 240-pounder inked a deal for a total of about $58 million over four years.

While the Chandler-to-Boston rumors seemed improbable to the naked eye from the start (at least cap-wise), there were ways to make the deal happen. Ainge could have packaged Jeff Green and Glen Davis in a sign-and-trade, throwing in a draft pick and cash considerations.

Unless Dallas or any other team had interest in Jermaine O'Neal, Boston could have waived the veteran big man under the amnesty clause to make cap space. Chris Wilcox would have never been signed to a $3 million mid-level exception. Instead, they could have signed veterans Kurt Thomas and/or Erick Dampier as affordable bench reinforcements.

Maybe this is all crazy talk. But wouldn't most fans rather see Chandler in Celtics green at four years, $60 million than Jeff Green for four years, $36 million and Brandon Bass for three years, $20 million? The Big Baby sign-and-trade with the Orlando Magic, which brought Bass to the C's, occurred immediately after the Chandler deal was finalized with New York.

If nothing else, Boston should have made a bigger try for Chandler, who said he was most impressed by Golden State Warriors coach Marc Jackson after New York. If Ainge and coach Doc Rivers had courted Chandler, he might have been more inclined to get involved in a deal that pushed the competitive scales for Boston.

Think about it: Chandler finished last season with a 67.9 field goal percentage, the best in the league and third-highest of all time (No. 1 and No. 2 on the list belong to a guy named Chamberlain--you might have heard of him). Chandler also won the 2012 Defensive Player of the Year Award, thanks to his solid down-low presence and rebounding.

With Chandler alongside Garnett and Pierce in the frontcourt and Rondo and Ray Allen starting at the guard positions, Boston would have been a favorite for the NBA Championship last year and potentially for years to come.

Drafting J.R. Giddens Over Mario Chalmers and DeAndre Jordan in 2008

Commissioner David Stern walked out to the NBA Draft podium in 2008, sporting his customarily smug look and holding the Celtics' late-round pick.

“With the 30th overall pick of the 2008 NBA Draft, the Boston Celtics select J.R. Giddens of the University of New Mexico.”

Ugh. Even then, much of Boston knew Ainge had missed two huge steals at their end-of-round position: Mario Chalmers and DeAndre Jordan.

Chalmers, a point guard out of Kansas known for gritty defense and reliable shooting, ultimately went to the Miami Heat. GM Pat Riley had his eyes on the young stud's competitive toughness, which has long since paid off for both parties.

Chalmers started at point in all five games of Miami's 2012 championship series over the Oklahoma City Thunder, leading the series in steals. He holds an average of 8.6 points and 3.6 assists per game over his five-year career in South Beach.

Ainge completely whiffed on a guard who ended up playing a crucial role for a perennial contender, instead picking a guard who only played 27 games in Boston before getting the boot. Giddens was traded to the Knicks, where he played another 11 games and then completely fizzled away. He now plays for Italian league team Basket Brescia Leonessa.

But Ainge's biggest miss of the 2008 NBA Draft was DeAndre Jordan, an athletic center out of Texas A&M who fell to the Los Angeles Clippers at pick 35. A superb rebounder and shot-blocker, the 6'11”, 250-pound Jordan somehow slipped out of the first round because of minimal offensive averages and speculation about his attitude.

Five years later, Jordan has a 6.5 rebound and 1.5 block per game average over his career, and his offensive production has risen each year. He's currently logging 8.8 points a contest in a shade over 24 minutes a game, and his .608 field goal percentage ranks second-best in the league.

Apparently, Boston actually tried to trade Garnett for Jordan and fellow Clipper Eric Bledsoe in last week's trade deadline, showing once and for all that Ainge rues his shoddy 2008 draft. Fans can only dream about how much success the Celtics would have with Pierce, Garnett and Jordan manning the frontcourt.

Chad Ford, ESPN's NBA Draft guru, wrote in his 2008 post-draft grades that, “if Jordan develops, he could get some GMs in hot water.” Ainge's blood must be boiling by now, knowing Jordan has more than developed into an NBA talent.

Consistently Ignoring a Decade-Long Fiasco at the Center Position

Throughout the past 10 years, most Boston sports fans have understood a few glaring issues with their main teams.

Red Sox fans still await a star shortstop to fill the void Nomar Garciaparra left when he was traded in 2004. New England Patriots supporters continue to look for secondary help since the losses of Ty Law and Lawyer Milloy.

Celtics fans, however, just want a reliable center, an asset Boston has arguably not been afforded since Robert Parish's departure 20 years ago.

Besides Perkins, who fulfilled his role with decent defense and rebounding (as well as quality field goal percentages), Ainge has completely struggled with the center position.

First, let's look at Mark Blount. The Pittsburgh alum peaked at 10.3 points and 7.2 rebounds in 2003-04, wowing Ainge into unabashedly signing the big man to a six-year, $42 million deal.

Apparently taking his newfound riches to his head, Blount immediately started a descent into eventual basketball obscurity. Even with added minutes, he failed to duplicate the seven rebound average and never really fit into the Celtics' offense.

Blount ultimately ended up in Minnesota as part of a package for Wally Szczerbiak, yet another meaningless deal in the long run for Boston.

Ainge can't be blamed completely for Blount's never-ending post-contract celebration, but the move certainly paved the way for what Celtics fans now realize is the GM's biggest flaw.

That brings us to Rasheed Wallace. To the average fan, the veteran big man known for his tendency to draw technical fouls might have seemed like a great addition to the Celtics for their 2009-10 run.

But 'Sheed was so physically out of shape and so mentally unfocused that he managed to hinder the Celtics in the playoffs more than he helped them. The Lakers out-rebounded Boston by 18 in Game 7 of the Finals, due in large part to his ineffective play down low.

Two veteran O'Neals came in for the 2010-11 season, one named Shaquille and one named Jermaine. They both had old knees and various injury concerns. Neither could run with the likes of Rondo or Allen, or play defense with Pierce or Garnett.

Shaq saw more time on the inactive list than he did on the floor, and Jermaine struggled to make an impact beyond some select defensive stands. He made nothing happen on post-up plays and failed to box out regardless of opponent size.

Other names just continue to highlight Ainge's inadequacies at the center position. Do you know where Michael Olowokandi, Theo Ratliff, Scot Pollard, Troy Murphy, Semih Erden, Chris Johnson, Mikki Moore, Ryan Hollins, Sean Williams and Patrick O'Bryant are right now?

The answer, as Alex Trebek might say, is “laughing all the way to the bank that Danny Ainge paid them to play for the Celtics.”

Boston can only hope that their GM provides more positives than negatives in the years to come, especially considering the not-so-distant inevitable departures of Pierce and Garnett. Celtics Nation will keep their fingers crossed that Ainge has learned from the aforementioned mistakes, at least before making his next big move.