B/R NBA Staff Roundtable: Biggest What-If Trades That Almost Happened

Bleacher Report NBA StaffFeatured ColumnistMay 20, 2020

B/R NBA Staff Roundtable: Biggest What-If Trades That Almost Happened

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    CHRIS CARLSON/Associated Press

    What if?

    No two words spark more discussion and debate in sports. What if your team's draft pick had been the star you expected? What if that injury had never happened? 

    Today, Bleacher Report is taking the big question and applying it to the trading block. We asked NBA writers to look back on real rumors about the game's biggest names to see just how different the history books would read had some of these deals gone through. 

Scottie Pippen to the Seattle Supersonics (1994)

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    Nathaniel S. Butler/Getty Images

    A plethora of what-ifs surround the initial post-Michael Jordan Chicago Bulls.

    The most intriguing of them may be what might have happened if the Scottie Pippen-led Bulls had managed to win Game 7 of the 1994 Eastern Conference Semifinals against the New York Knicks. They would have then faced the Indiana Pacers, who they'd defeated four times in five tries during the regular season.

    If Pippen had managed to earn his own way to the Finals, would he still have relinquished his new leadership role to Jordan? 

    Instead, the Bulls fell, and general manager Jerry Krause had more questions than answers because of Jordan's retirement and Pippen's advancing age during the 1994 offseason.

    Prior to draft night, Krause floated the idea of swapping Pippen for superstar forward Shawn Kemp and sixth man Ricky Pierce. Jordan reportedly even pushed Seattle SuperSonics head coach George Karl to take the deal, per the Chicago Tribune's Sam Smith: "You'll be getting the best of it."

    Would Jordan have returned to Chicago without Pippen? 

    "Probably not," he told ESPN's J.A. Adande. "I could have played with Shawn, but I wouldn't have been as comfortable as I was with Scottie."

    If Jordan had returned, would he have then stood alongside Kemp against Gary Payton and Pippen in the 1996 Finals? Pippen may have been the player best suited to guard Jordan. He and Payton combined for 19 All-Defensive teams between them and could have given the hypothetical pair all they could handle.

    Could Jordan have harnessed the best from Kemp? Would the Sonics have appeased Pippen financially prior to the 1997-98 season? 

    Things worked out just fine for Jordan and the Bulls, but one can't help but wonder how they would have changed if the Sonics had accepted the deal and acquired one of the NBA's best small forwards of all time.

    Preston Ellis

Allen Iverson to the Pistons (2002)

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    JEFF KOWALSKY/Getty Images

    Imagine if this trade, a scuttled four-team deal from 2000, as reported by Ira Winderman of the South Florida Sun-Sentinel, had gone down.  

    The Philadelphia 76ers almost sent Allen Iverson and Matt Geiger to the Detroit Pistons and Toni Kukoc to the Los Angeles Lakers. The deal also included Eddie Jones going from the Charlotte Hornets to Philadelphia and Glen Rice moving from the Lakers to the 76ers, among other pieces. 

    Per Winderman, Geiger's trade kicker ultimately ended the deal.

    Instead, Iverson went on to earn the NBA's Most Valuable Player award in 2000-01, leading the Sixers to the NBA Finals against Shaquille O'Neal, Kobe Bryant and the Lakers.

    Los Angeles ended up sending Rice to the New York Knicks in the multi-player trade that had Patrick Ewing off to the Seattle SuperSonics toward the end of his career and Horace Grant landing in Los Angeles, where he helped the Lakers beat Iverson and the 76ers in the 2001 Finals.

    Although Philadelphia never won a title with Iverson, it enjoyed a legendary run, especially when the Sixers got a win at Staples Center in Game 1 of the '01 Finals.

    At that point in his career, Rice was on the downswing. Jones spent most of the next few years with the Miami Heat (although he missed out on the 2005-06 championship run). Jerry Stackhouse, who would have gone to the Hornets in the deal, stuck in Detroit and had a career year, averaging 29.8 points during the 2000-01 season. He was eventually traded to the Washington Wizards for Richard "Rip" Hamilton, who proved to be a vital piece of the Pistons' 2003-04 championship squad.

    Finally, Kukoc would have been an interesting fit for the Lakers as a third scorer, but he was instead traded to the Atlanta Hawks in a deal for Dikembe Mutombo. He averaged 19.7 points per game for the Hawks, and Mutombo was huge for the Sixers in their attempt to deal with O'Neal in the Finals. 

    Would the Pistons have won more than their one title with Iverson instead of Hamilton? Possibly. And what of Geiger, who blew up the initial deal? He was out of the NBA by 2002.

    Eric Pincus

Kobe Bryant for LeBron James (2006)

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    Andrew D. Bernstein/Getty Images

    The blockbuster to end all blockbusters was actually bounced around in 2007. Or rather, the Los Angeles Lakers gauged the Cleveland Cavaliers' willingness to make a LeBron James-Kobe Bryant mega-swap, per ESPN's Brian Windhorst.

    The Cavs unsurprisingly said no, then they sought ways to bring Bryant to Cleveland to play alongside James. The Lakers unsurprisingly also said no.

    This would have shifted basketball's tectonic plates in a way to make the entire landscape unrecognizable.

    At the time, a 22-year-old James had just lifted the Cavaliers to their first Finals appearance, while Bryant had picked up a pair of scoring titles, trying but failing to elevate an undermanned roster. L.A.'s third-leading scorers in 2005-06 and 2006-07 were Smush Parker and Luke Walton, respectively. It was bleak.

    Had the Lakers landed basketball's prized up-and-comer, perhaps they would have focused on a patient restructuring around him. Since they didn't, they instead sought veteran accelerators, snagged Pau Gasol in February 2008 and won championships in both 2009 and 2010.

    Had the Cavs lured Bryant to Northeast Ohio, they surely wouldn't have stopped there. The actual race to put win-now players around James, which eventually netted Mo Williams, Antawn Jamison and Shaquille O'Neal, would have started even earlier and perhaps seen even bigger home-run swings to capitalize on Bryant's window.

    If James gets to L.A., does he then skip the stint in South Beach? Does he reign over the Western Conference in a way that prevents the rise of the Golden State Warriors' dynasty? If Bryant goes to the Cavaliers, is he the one who snaps Cleveland's championship drought? Could he have stopped the Boston Celtics from escaping the East in 2008?

    You're not only rewriting the history books if this deal goes down; you're raising and lowering championship banners around the NBA.

    Zach Buckey

Kobe Bryant to the Detroit Pistons (2007)

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    Duane Burleson/Associated Press

    Following the Los Angeles Lakers' five-game Finals loss to the Detroit Pistons in 2004, they underwent a reset. Shaquille O'Neal was dealt to the Miami Heat. Phil Jackson was fired in favor of Rudy Tomjanovich.

    In the wake of those changes, the Kobe Bryant-led Lakers missed the playoffs altogether in 2004-05 and failed to escape the first round in the two ensuing seasons. 

    In 2007, Bryant reached a breaking point and initially sought a trade.

    "I would like to be traded, yeah," Bryant told 1050 ESPN Radio in New York. "Tough as it is to come to that conclusion, there's no other alternative, you know?" 

    Obviously, the shooting guard ended up remaining with the Purple and Gold. But he was almost dealt to the Pistons, and the parameters of the deal vary depending on who you ask.

    Per Ken Berger of CBS Sports (h/t MLive.com's Aaron McCann), the Pistons' package featured Rip Hamilton, Rodney Stuckey, Jason Maxiell and two first-round picks. Yahoo Sports' Vincent Goodwill reported that Detroit was offering Hamilton, Tayshaun Prince, Amir Johnson and a future first-round pick. 

    After winning a title in 2004 and falling to the San Antonio Spurs in the 2005 Finals, the Pistons came up short in the Eastern Conference Finals twice in a row, losing to the Miami Heat in 2006 and the Cleveland Cavaliers in 2007. Placing Bryant alongside Chauncey Billups and Rasheed Wallace may have changed the outcome in 2008 and created quite the matchup against the Big Three-era Boston Celtics.

    Instead, the Memphis Grizzlies traded Pau Gasol to the Lakers for Kwame Brown, Javaris Crittenton, Aaron McKie, Marc Gasol and two future first-round picks. That move led the Lakers to two more titles and closed the door on one of the greatest what-ifs in NBA history.

    Preston Ellis

Kevin Garnett to the Lakers (2007)

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    Melissa Majchrzak/Getty Images

    Before Kevin Garnett was traded to the Boston Celtics in 2007, he was a target of the Los Angeles Lakers, who hoped to pair the All-Star forward with Kobe Bryant.

    The Minnesota Timberwolves spoke to several teams, and owner Glen Taylor discussed a deal with late Lakers owner Jerry Buss. A deal built around Lamar Odom and Andrew Bynum was a possibility.

    At the time, Bryant was also in turmoil, demanding a trade that offseason because, in part, he didn't feel the Lakers were committed to building a championship roster around him. Additionally, L.A.'s front office was divided between Jeanie Buss (business side) and Jim Buss (basketball), bleeding into several public radio interviews that gave the impression the franchise was in turmoil and unlikely to rebound in the post-Shaquille O'Neal era. 

    None of this appealed to Garnett, who was looking for stability and the opportunity to win a title. He ended up with the Boston Celtics.

    The Lakers remained patient, stabilized and eventually made their own blockbuster deal for Pau Gasol. A Garnett-Bryant Lakers would have been something to watch, but it would have deprived the world of two epic NBA Finals of Garnett vs. Bryant, with the Celtics winning in 2008 and the Lakers in 2010.

    Eric Pincus

Dwyane Wade to the Bulls (2008)

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    Lynne Sladky/Associated Press

    Dwyane Wade called it "a dream come true" to join his hometown Chicago Bulls ahead of his age-35 season in 2016. The Bulls tried dreaming it into existence nearly a decade prior.

    Once Chicago snagged the No. 1 pick in 2008, the Chicago Tribune reported the Bulls were trying to package it in a deal to acquire Wade from the Miami Heat (h/t ESPN).

    Chad Ford, then with ESPN, theorized Chicago could offer something like the pick, Joakim Noah, Thabo Sefolosha and Drew Gooden's expiring deal, while Miami could rebuild around Derrick Rose, Michael Beasley and whatever it could get in a Shawn Marion trade.

    It's entirely possible that had this happened, the Heat and Bulls could have traded realities over the ensuing decade. If nothing else, the 2010 offseason would have grown even more fascinating.

    Then, the Bulls were "a Luol Deng trade to the Clippers away" from inking the Big Three of Wade, LeBron James and Chris Bosh, per K.C. Johnson of the Chicago Tribune. Instead, those three took their talents to South Beach, leaving the Bulls to spread their funds among Carlos Boozer, Kyle Korver, Ronnie Brewer and Keith Bogans.

    If the Bulls had landed Wade in 2008, maybe that added familiarity would have nudged them ahead in the superteam sweepstakes and turned Chicago into a four-time Finalist and two-time champion. If the Heat had to restart with Rose and Beasley, would the former still skyrocket to league MVP in his third NBA season? And would the latter have received a longer leash than the two seasons Miami actually gave him?

    The Eastern Conference hierarchy—and maybe the Association's entire power structure—could have changed overnight.

    Zach Buckey

Amar'e Stoudemire to the Warriors for Stephen Curry (2009)

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    Barry Gossage/Getty Images

    Steve Kerr and Stephen Curry were always going to end up together. Their meeting place just wasn't originally Oakland.

    Per Tim Kawakami, then of the San Jose Mercury News, Kerr claimed that when he was general manager of the Phoenix Suns during the 2009 draft, he almost traded Amar'e Stoudemire and the No. 14 pick (which became forward Earl Clark) to the Golden State Warriors for Curry. However, due to Stoudemire's balky knees, the deal fell through.

    Since Stoudemire became a free agent in 2010, it's possible he would only have stayed in Golden State for one season. If he departed, then the Warriors would have been left with a future core of...Monta Ellis. Yuck.

    Perhaps Chris Cohan still would have sold the team to Joe Lacob and Co. in 2010, and that could have been enough to make it a perennial playoff team in time. But three titles in five years? That would have been unthinkable.

    Phoenix's side of this deal is much more interesting.

    Injecting Curry into the seven-seconds-or-less culture would have been intoxicating.

    Stoudemire's departure could have created small-ball years before its proliferation with Mike D'Antoni relying on Grant Hill and Jared Dudley at power forward. In addition, Curry and Steve Nash running a pace-and-space offense could have broken the brains of opposing defenses in 2010. They would have been appointment television every night and could have led to a long-awaited Finals berth for Nash.

    And Curry might still be bombing away for the Suns in 2020.

    Phoenix is not the Bay Area, so the Suns may not have become the center of the basketball world the way the Warriors were. But yes, Phoenix fans. With Stephen Curry, there'd be no decade-long playoff drought. You'd be in the thick of things every year.

    Mandela Namaste

Tyson Chandler to the Thunder (2009)

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    Bill Haber/Associated Press

    At the 2009 trade deadline, the New Orleans Hornets dealt starting center Tyson Chandler to the Oklahoma City Thunder in a pure salary-dump move, getting back the expiring contracts of Chris Wilcox and Joe Smith. The deal was done, agreed to, called in to the league office and announced.

    And then Chandler failed his Thunder physical, causing the trade to be rescinded.

    The trade wasn't a blockbuster—Chandler was a very good player but had yet to make an All-Star team at that point in his career—but consider the ripple effect.

    If the Thunder had landed Chandler, they would have had a 26-year-old shot-blocking center with playoff experience to pair with the nascent duo of Kevin Durant and Russell Westbrook (they would draft James Harden and Serge Ibaka that June). 

    They wouldn't have made the trade for Kendrick Perkins two years later to fill that spot, meaning the Boston Celtics' 2008 and 2010 Finals teams wouldn't have been broken up as soon. Maybe they would have been able to make another run.

    And Chandler was a significantly better player than Perkins, so if they had him playing those center minutes, maybe they would have won a title and not felt compelled to break up the Durant-Westbrook-Harden trio to save money. Durant might not have ultimately left for the Golden State Warriors.

    Beyond that, if Chandler had gone to Oklahoma City, he almost definitely wouldn't have ended up in Dallas during the summer of 2010. He was the second-most important player on the Mavericks' 2010-11 championship team, which wouldn't have won that title without him.

    That would mean Dirk Nowitzki, one of the greatest players of his generation, likely would have retired without a ring. The team the Mavericks beat in the Western Conference Finals that year was...the Thunder, then in the first deep playoff run of the Durant-Westbrook era.

    Sean Highkin

Amar'e Stoudemire to the Cavaliers (2010)

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    Mark Duncan/Associated Press

    As the 2010 trade deadline approached, the Cavaliers were desperate to upgrade their roster for the last playoff run before LeBron James' impending free agency. They reportedly came close to a deal for Amar'e Stoudemire, also an upcoming free agent, which would have sent second-year forward J.J. Hickson and veteran center Zydrunas Ilgauskas to the Phoenix Suns.

    The Cavs pulled out of the deal, deciding they wanted to hang onto Hickson in case James left and they had to pivot to a rebuild. They instead traded Ilgauskas to the Washington Wizards for Antawn Jamison.

    Stoudemire was still an All-NBA player in 2010 and would have been a huge upgrade for the Cavs. That year, he helped lead the Suns to the Western Conference Finals, where they lost to the Los Angeles Lakers.

    If Cleveland had landed him, it may have fared better than the infamous loss to the Boston Celtics in the second round of the playoffs. It could have faced the Orlando Magic in the Eastern Conference Finals, and if it had won that series, we may have gotten the elusive LeBron James-Kobe Bryant Finals.

    As for how a run to the Finals or a title would have affected James' free agency? By all accounts, his plot to team up with Dwyane Wade and Chris Bosh was hatched several years in advance. Maybe winning a title in Cleveland would have changed things, but James was playing with Mo Williams and a broken-down Shaquille O'Neal by that point and still would likely have viewed the Miami Heat's situation as an upgrade.

    Stoudemire would still probably go to the New York Knicks, who were desperate to land a big name after striking out on James, Wade and Bosh.

    Sean Highkin

Chris Paul to the Lakers (2011)

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    Layne Murdoch/Getty Images

    If you were a basketball fan in 2011, you probably remember this like it was yesterday.

    In what seemed like an unprecedented and perhaps illegal show of power, a proposed three-team trade that would send perennial All-NBA point guard Chris Paul to the Los Angeles Lakers was nixed by NBA Commissioner David Stern.

    At the time, Lakers fans were outraged at Stern, and they're still perhaps in the right. But the commissioner had his reasons for vetoing the trade and claimed he was acting on behalf of the New Orleans Hornets, Paul's incumbent franchise and one lacking an owner since George Shinn had sold the team back to the league in 2010. 

    Whether Stern was actually acting in his capacity as a small-market franchise owner worried about losing its best player ever or merely as the commissioner of the NBA, wary of superteam proliferation, remains uncertain. But nearly a decade into the future, it's undeniable that this non-trade irrevocably altered the trajectory of the league.

    With hindsight, it might be for the best (for the Lakers, at least) that this trade was nixed. Given what we learned about Paul during his subsequent tenures with the Los Angeles Clippers and Houston Rockets, he seems to be a domineering personality at times, a character trait that may have led to clashes with the similarly alpha Kobe Bryant.

    In addition, James Harden's ball-dominant tendencies irked Paul in Houston, so you can only imagine how he might react to Bryant, perhaps the most notorious ball-commandeering superstar of the 21st century. 

    But the fact that we'll never get a chance to know bothers many Lakers fans to this day, and it remains one of the great loose threads in NBA history.

    Mandela Namaste

Kevin Love to the Warriors for Klay Thompson (2014)

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    Rocky Widner/Getty Images

    The dynastic Golden State Warriors of the 2010s wouldn't have reached the same heights if anything in their pre-title construction had gone differently. Hire someone other than Steve Kerr as head coach and they're a different team. Fail to lock Stephen Curry into a four-year, $44 million deal and nothing's the same.

    The deal they nearly struck with the Minnesota Timberwolves in 2014 is another example.

    The particulars varied, and it's possible Golden State might have also dealt Draymond Green or Harrison Barnes along with David Lee and Klay Thompson for then-25-year-old star Kevin Love. Thompson was the sticking point, one viewed by local and national voices, myself included, as a player who'd never be as valuable as Love.

    The consensus was that the Warriors had to seize the opportunity to add Love and trade Thompson in the process.

    Jerry West and, if you believe other reports, Kerr felt differently. West, a consultant with the team and arguably the most respected executive in league history, reportedly threatened to resign if Thompson was included in the deal.

    In the end, Golden State stood pat. Kerr made the tactical and philosophical adjustments Mark Jackson never could to optimize the roster, and Thompson became an All-Star and one of the greatest shooters in history. Green took over the power forward spot Love would have occupied and gave the Warriors a defensive identity that wouldn't have taken shape without him.

    If the Warriors had dealt Thompson and others for Love, they might have been a great team anyway. But it feels safe to assume they wouldn't have made five straight Finals runs, propelled in large part by the players they nearly traded away.

    Grant Hughes

Paul George to the Cavaliers (2017)

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    Michael Conroy/Associated Press

    Before Kyrie Irving was traded to the Boston Celtics in the summer of 2017, the Cleveland Cavaliers almost dealt another member of their Big Three.

    With Paul George telling the Indiana Pacers that he wouldn't be re-signing with them, the Cavs made a hard push to pair him with LeBron James and Irving.

    The cost? Kevin Love.

    The Denver Nuggets wanted Love and were willing to give up Gary Harris, then a 22-year-old shooting guard who was averaging 14.9 points on 42.0 percent from three. Harris would go to the Pacers, who would also be getting other pieces in the deal, per ESPN.

    All three teams agreed on the trade during a conference call before Pacers general manager Kevin Pritchard backed out, later trading George to the Oklahoma City Thunder for Victor Oladipo and Domantas Sabonis.

    Had George been sent to the Cavaliers, Cleveland would have been more likely to keep Irving, or at least trade him in more of a win-now deal instead of one highlighted by a draft pick. James and George would have both become free agents in 2018, with their success together in 2017-18 likely dictating where each would go on to sign. The Cavs-Golden State Warriors rivalry would certainly have taken an interesting turn, as well.

    The Nuggets wouldn't have signed Paul Millsap to a three-year, $90 million deal with Love already in place, but the Pacers would have suffered most.

    Both Oladipo and Sabonis have become franchise pillars and All-Stars on what's become one of the better teams in the East. Harris has regressed in Denver, now looking like a borderline starter instead of a future All-Star wing.

    Flipping Love for George would have been a franchise-saving move for Cleveland, and the Pacers now look like geniuses for breaking off the trade.

    Greg Swartz

Kyrie Irving to the Bucks (2017)

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    Jason Miller/Getty Images

    After three runs to the Finals and one championship, Kyrie Irving decided he no longer wanted to play alongside LeBron James in the summer of 2017.

    At the time, Irving was just 25, already a four-time All-Star who had averaged 25.2 points and 5.8 assists in 2016-17 even while sharing the ball with James and Kevin Love. He had two years remaining on a five-year, $80 million contract, meaning his trade value was quite high.

    Before Cleveland ultimately dealt him to the Boston Celtics, the Cavs had another significant offer on the table. The Milwaukee Bucks needed a second star to pair with Giannis Antetokounmpo and were willing to sell off some of their young talents to do so.

    ESPN's Zach Lowe reported that the Bucks offered Khris Middleton and Malcolm Brogdon to Cleveland for Irving, a deal that would have changed the Eastern Conference for years to come.

    Brogdon was coming off Rookie of the Year honors but hadn't yet evolved into the point guard currently averaging 16.3 points, 4.7 rebounds and 7.1 assists for the Indiana Pacers. While Middleton has made All-Star teams each of the past two seasons and is averaging 19.7 points, 5.8 rebounds and 4.1 assists over the last three years, he was putting up just 14.7 points per game during the 2016-17 season.

    Both were viewed as good role players, but it wasn't a strong enough offer for a budding superstar like Irving.

    Had Cleveland made the deal, the Cavs' lineup of Brogdon, Middleton, James, Love and Tristan Thompson would likely have remained at the top of the conference rather than the version that would ultimately stumble to the No. 4 seed before James dragged it to the Finals. The Cavs would have had length, passing and defense all over their starting lineup, the perfect makeup to take down a then-Kevin Durant-led Golden State Warriors team.

    Perhaps with Middleton and Brogdon, James would have considered staying in Cleveland instead of leaving for the Los Angeles Lakers after watching the Irving-Isaiah Thomas trade go down in flames.

    For Milwaukee, not making the deal was a blessing in disguise. Irving would have knee surgery and miss the entire 2018 postseason, and the topic of his free agency in 2019 could have been a distraction for a Bucks team that was just establishing a great level of chemistry.

    Milwaukee likely wouldn't have secured the No. 1 seed in the East the past two years, and there's a good chance Irving would still have departed for his hometown Brooklyn Nets, leaving Antetokounmpo's shadow much like he previously left James'.

    The Cavs could still be the best team in the East had the deal been completed, and Milwaukee's reign over the conference never would have begun.

    Greg Swartz


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