1) Lakers trade Wilt Chamberlain to the Bulls and the Blackhawks trade Bobby Hull to the Kings (1972)

We may as well start here with arguably the most implausible yet valid trade rumor in NBA history. Similar to how the NBA was dealing with the upstart ABA at the time, the NHL had its own striving, neophyte rival in the WHA in the early ’70s. Hull was a franchise legend with the Chicago Blackhawks but was upset with his contract in 1972 and threatening to pull a Rick Barry by defecting to the Winnipeg Jets of the WHA. Jack Kent Cooke, who owned both the Lakers and the Los Angeles Kings at the time, found out about this situation and contacted Blackhawks and Bulls owner Arthur Wirtz with a wild idea. Cooke would trade Chamberlain, who was coming off a Finals MVP award but was similarly disgruntled about his paychecks, to the Bulls, while Wirtz would send Hull to the Kings. This could grant instant star power and legitimacy to young Bulls and Kings franchises while placating two aging superstars. The mechanics of how this would actually work would be fascinating but sadly we never found out, as the trade talks never progressed into tactile stages. Hull signed with Winnipeg and spent the rest of his career in the WHA, while Chamberlain played one more season with the Lakers, reaching another NBA Finals, before retiring.

2) Bulls trade #3 draft pick (used on Michael Jordan) to Clippers for Terry Cummings (1984)

It might be the ultimate NBA hypothetical of an unstoppable force meeting an immovable object. Could Jordan, the most singularly minded basketball machine in history, have turned the moribund, snakebitten Clippers into a championship franchise? Or would the Clippers curse have ruined his career, just like it did so many other superstars? We almost found out, as it was reported just days before the 1984 NBA Draft that the Bulls were shopping the #3 overall pick, which they eventually used on Jordan. Their most motivated buyer was the Clippers, who were looking to unload the disgruntled Cummings, who would have appreciated a return to his hometown of Chicago. The deal ultimately fell through, of course, and the Bulls held onto the pick while the Clippers eventually traded Cummings later that summer to the Bucks. Amazingly, the Bulls reportedly almost traded Jordan to the Clippers again in 1988. Though their superstar was coming off his first MVP season, Chicago owner Jerry Reinsdorf seriously considered an offer from Donald Sterling of the #1 and #6 draft picks, plus three (undisclosed) players. Ultimately, Reinsdorf wisely decided that Jordan was too talented and profitable to send him away.

3) 76ers trade Charles Barkley to Lakers for James Worthy and Elden Campbell (1992)

How close did this trade come to happening? So close that Barkley went out day drinking to celebrate it only to find out that the 76ers had backed out of the deal and he would have to play for them that night with a buzz. Rumors swirled throughout the ’91-’92 season that a 76ers trade of their disgruntled superstar was imminent. At some point, likely right before the February trade deadline, the Sixers had a deal in place to send Barkley and Ron Anderson to the Lakers for James Worthy and Elden Campbell, but backed out at the last minute. Barkley closed out the season with Philadelphia and was traded that summer to the Suns for Jeff Hornacek, Andrew Lang, and Tim Perry. It’s debatable which trade was theoretically better for Philly but no doubt both were certainly not a solid return for Barkley, as Worthy was undoubtedly a great player but was on a downswing already by ’91-’92.

4) Rockets trade Hakeem Olajuwon to Heat for Glen Rice and others (1992)

We’ve mentioned elsewhere how weird it was seeing Olajuwon finish out his carer in a Raptors uniform but even more uncanny is thinking about him joining the Heat in his prime a decade earlier. It almost happened because Olajuwon and the Rockets were an unhappy union in the summer of 1992. The ’91-’92 season had ended disastrously, with the Rockets missing the postseason for the first time in Olajuwon’s career. Late in the season, team management had accused its star center of faking an injury to sit out meaningless games and subsequently suspended him. Olajuwon’s agent demanded a trade and the Rockets definitively fielded offers from the Heat, SuperSonics, Lakers, Trail Blazers, and Clippers. The deal with Miami came the closest to fruition and it would have been a coup for the Heat, who offered Rony Seikaly, Harold Miner, and Grant Long. When the Rockets demanded Steve Smith or Glen Rice be included in the package, the Heat mistakenly balked, missing out on the chance to set up an epic Florida in-state rivalry between Olajuwon and Orlando’s Shaquille O’Neal. Olajuwon and the Rockets mended fences and had a quick turnaround, winning back-to-back championships in 1994 and 1995.

5) Pistons trade Dennis Rodman to Suns for Richard Dumas (1993)

What are the odds that a trade involving Rodman would fall through due to the personal issues of a different player involved in the deal? In this case, it was Dumas, a versatile forward coming off a breakout rookie season for the Suns in ’92-’93 but struggling with drug abuse. He had previously been suspended for the entire ’91-’92 season due to a failed drug test and was spending the 1993 offseason in a substance abuse aftercare program. This latter fact was not known initially by Pistons executives and they backed out of the trade in September of 1993 once they realized that Dumas was still in recovery. Whether that assessment was fair or not, it did work out in their favor as Dumas was suspended again for the ’93-’94 season and his NBA career was effectively over at that point. Not that keeping Rodman was fruitful for Detroit either. They were still forced to trade the mercurial forward a few weeks later to the Spurs in a disastrous deal that augured the end of the “Bad Boys” era.

6) Bulls trade Scottie Pippen to SuperSonics for Shawn Kemp (1994)

SuperSonics fans have long lamented the team’s immediate trading of Pippen after drafting him in 1987 (in exchange for Olden Polynice) but the fanbase arguably tanked the team’s ability to bring him back seven years later. In the summer of 1994, both the Sonics and Bulls were coming off disastrous postseason performances. Chicago was eliminated in a second round series that culminated in Pippen refusing to re-enter a game after coach Phil Jackson drew up a final play for Toni Kukoc. Seattle was stunned in the first round as a #1 seed and many were blaming it on the inexperience of young star Shawn Kemp. Jerry Krause offered Pippen to the Sonics in exchange for Kemp and a first round pick and it seemed like a done deal until news of the trade leaked through the media. Sonics fans were furious at the prospect of losing their high-flying, electrifying young forward and their backlash supposedly convinced Seattle owner Barry Ackerley to scuttle the deal. Pippen would remain a trade target for the rest of his time in Chicago, with the Bulls reportedly almost dealing him to the Clippers, Celtics, and Suns over the next few years, until finally shipping him to the Rockets in 1999.

7) Pistons trade Isiah Thomas to Knicks for Tony Campbell, Tim McCormick, and a first round pick (1994)

With Michael Jordan retired, the Knicks were an obvious favorite in the Eastern Conference in ’93-’94 but had one major problem. Once Doc Rivers was waylaid early in the season with a knee injury, they lacked a steady veteran at point guard. In early January, they seemed to have an agreement in place to acquire Thomas from the Pistons in exchange for Tony Campbell, Tim McCormick, and a first round pick but the deal fell through for undisclosed reasons. Pistons management maintained that they decided that the return package was too slight while rumors swirled that Thomas had actually exercised an unofficial no trade clause to keep himself in Detroit. Though he wasn’t quite an All-Star level talent anymore at age 32 (and would soon after suffer an Achilles’ tear that ended his career), Thomas himself argued that he could have been the difference maker for the Knicks in that postseason. They reached the NBA Finals without him after trading for a different aging point guard in Derek Harper but lost in game seven in an infamously terrible performance from John Starks. Thomas would later argue that he would have altered the game by keeping the ball out of Starks’ hands. Thomas and the Knicks would eventually come together in 2003, in a calamitous five year run as the team’s president and coach.

8) Trail Blazers trade Clyde Drexler to SuperSonics for Kendall Gill (1995)

It was no secret that Trail Blazers owner Paul Allen gave his new general manager Bob Whitsitt a directive to rebuild in the summer of 1994. That meant that the face of the franchise for over a decade, Drexler, was on the trading block. He was eventually dealt to the Rockets in exchange for Otis Thorpe and a first round pick but that was only after a trade negotiation with the SuperSonics broke down. Seattle offered Kendall Gill, who at the time was showing signs of All-Star potential as a young shooting guard. This was definitely a better deal at the time and in retrospect for Portland but Whitsitt got cold feet over trading his showcase star to Portland’s biggest rival and possibly spurring them to a championship. The Sonics were upset that spring in the Conference Quarterfinals by the Lakers, while Drexler and the Rockets won the championship.

9) Raptors trade Tracy McGrady and a first round pick to 76ers for Larry Hughes (1999)

Almost as soon as the Raptors drafted him with the ninth overall pick in 1997, McGrady’s time with the team seemed like a ticking clock leading down to his inevitable departure. Such was the reality at the time for the still young franchise, which struggled to lure and retain star players due to its northern locale and the then cratering Canadian dollar. Possessing two rising superstars in McGrady and Vince Carter (whom they drafted in 1998) was therefore an obviously temporary condition and in 2000, the Raptors opted to bet their future on Carter, as they traded McGrady to the Magic. They only got a first round draft pick in return and they used it on Fran Vazquez, who never played in the NBA. But the rate of return would have been arguably even worse if they had gone through with a proposed deal in 1999 to send McGrady and a first round pick to the 76ers for Larry Hughes. Though this was obviously a raw deal in retrospect for Toronto, it would have pretty intriguing for Philadelphia, who could have paired McGrady and Allen Iverson in the back court for years to come. It supposedly fell apart due to Stephen A. Smith breaking the story and the Raptors subsequently getting cold feet.

In the same summer that Kobe Bryant was being shopped around but ultimately stayed in Los Angeles, the Timberwolves did everything short of placing a “for sale” sign around [Kevin] Garnett’s neck

10) 76ers trade Allen Iverson to the Pistons in a four-team deal (2000)

Speaking of Iverson, the Philadelphia hero almost got traded out of town right before he began truly crafting his legend in the city. On the cusp of what would eventually be his MVP season, he was part of a four-team trade that, in principle, would send him to the Pistons. It’s unclear exactly which players were part of the overall package, but the rumored deal involved the Sixers, Pistons, Lakers, and Hornets, and reportedly as many as 12 players, including notable names Iverson, Eddie Jones, Glen Rice, Toni Kukoc, Anthony Mason, Christian Laettner, and Jerry Stackhouse. Did this massive blockbuster fall apart because one or more of the teams chickened out at the last minute? Or because one of the star players involved put a kibosh on it? Nope. Instead, it was veteran Sixers backup center Matt Geiger who derailed the trade by refusing to waive his no trade clause to go to Detroit. An improbable sidetracking of a transaction that would have completely reshaped the Eastern Conference for years.

11) Lakers trade Kobe Bryant to Pistons for Richard Hamilton, Tayshaun Prince, Amir Johnson, and a first round pick (2007)
12) Lakers trade Kobe Bryant to Bulls for Luol Deng, Joakim Noah, and Tyrus Thomas (2007)

There was no secret around the NBA that Bryant was fed up with the Lakers following their first round exit in the 2007 playoffs. Exhausted by the franchise’s slow bore roster building, he made quite public demands that the organization bring back Jerry West as general manager. Bryant was also still being dogged by accusations that he had run Shaquille O’Neal out of town years earlier, precipitating the Lakers’ decline from title favorites to also-rans. Several offers poured in and two almost came to fruition. The first would have sent Bryant to the Pistons in exchange for Richard Hamilton, Tayshaun Prince, Amir Johnson, and a first round pick. The other would have had Bryant following in Michael Jordan’s footsteps on the Bulls, in exchange for Luol Deng, Joakim Noah, and Tyrus Thomas. Each are equally intriguing as “what if” scenarios, as the Pistons could have extended their stranglehold on the Eastern Conference while the Bulls were a team on the rise. While Bryant vetoed the Pistons trade, he admitted later after retiring that he would have approved the trade to Chicago, but the deal ultimately fell through. It’s long been rumored that the Lakers also offered Bryant to the Cavaliers that summer in exchange for LeBron James but even if that’s real, it’s doubtful Cleveland took this overture seriously.

13) Timberwolves trade Kevin Garnett to Suns, Suns trade Amare Stoudemire to Hawks and Shawn Marion to Celtics, Celtics trade first round pick to Timberwolves (2007)
14) Timberwolves trade Kevin Garnett to Lakers for Andrew Bynum, Lamar Odom, and other undisclosed players and picks (2007)

In the same summer that Kobe Bryant was being shopped around but ultimately stayed in Los Angeles, the Timberwolves did everything short of placing a “for sale” sign around Garnett’s neck. According to the man himself, his three trade destination requests were the Suns, Lakers, or Celtics. A complex deal was on the table which would send Garnett to Phoenix, Shawn Marion to Boston, Amare Stoudemire to Atlanta, and a first round pick from Boston to Minnesota, but Garnett vetoed it, as he didn’t want to play on the Suns without Stoudemire or Marion. Jerry Buss supposedly then had a handshake agreement with T-Wolves owner Glen Taylor to trade Garnett for a package built around Andrew Bynum and Lamar Odom but general manager Kevin McHale instead agreed to trade him to Boston for Al Jefferson, two first round picks, and a few other pieces. Lakers fans were irate, claiming that McHale and Celtics GM Danny Ainge were conspiring to keep Garnett away from Los Angeles but Taylor would later claim he was swayed by Jefferson’s potential and afraid to send Garnett to a Western Conference rival. The Lakers eventually landed a star big man in Pau Gasol (and didn’t have to give up Odom or Bynum in the process) and faced off against the Celtics in the 2008 and 2010 NBA Finals.

15) Suns trade Amare Stoudemire to Cavaliers for J.J. Hickson, Zydrunas Ilgauskas, and a first round pick (2010)

With LeBron James set to hit free agency that summer, the Cavaliers were desperate to land an All-Star caliber player at the 2010 trade deadline. They found a willing partner in the Suns, another franchise about to be altered by the subsequent offseason free agent spending frenzy. Phoenix knew its star center Stoudemire was ready to move on when his contract expired at the end of the ’09-’10 season and the frugal franchise was listening to offers to at least get a return on his departure. A beat-up, 34-year-old Ilgauskas and a late first round pick were basically throw-ins, as the Suns were interested in the young Hickson, who was flashing some promise at age 21. Reportedly, that long-term potential of Hickson is what ultimately caused the Cavaliers to renege on the deal. They instead exchanged Ilgauskas and a first rounder for an aging Antawn Jamison at the deadline and the rest is history. James and Cleveland were eliminated by the Celtics in the Conference Semifinals, the Suns hung on to Stoudemire and reached the Conference Finals, and the two superstars signed contracts with the Heat and Knicks, respectively. According to Stoudemire years later, he believes his presence in Cleveland would have convinced James to re-sign and he himself would have stayed there with him long term, completely altering the Eastern Conference of the ’10s.

16) Hornets trade Chris Paul to Lakers for Lamar Odom, Goran Dragic, Louis Scola, and Kevin Martin; Rockets receive Pau Gasol (2011)

This one was agreed to in principle by all three sides. The only issue was that one side was technically the NBA league office itself, which took control of the Hornets after buying out owner George Shinn in 2010. Though Hornets general manager Dell Demps spearheaded the deal in December of 2011 just as the lockout was lifted for the ’11-’12 season, commissioner David Stern stepped in quickly and vetoed it as the technical “owner” of the franchise. Stern would later claim that he only cancelled the transaction because Demps was technically not authorized at the time to make it but reports eventually surfaced that the commissioner’s hand was forced by NBA owners who were skittish over the new bargaining agreement terms and the burgeoning power of star players to choose their playing destinations (this was especially true of Cavs owner Dan Gilbert, who was still smarting over LeBron James’ departure for Miami one year prior). Paul was traded a few days later to the other Los Angeles team, the Clippers, for an arguably vastly inferior package of Eric Gordon, Al-Farouq Aminu, Chris Kaman, and a first round pick. It completely turned around the fortunes of that franchise while the Lakers fell into a prolonged slump, eventually missing the postseason for six straight seasons.

17) Timberwolves trade Kevin Love to Warriors for Klay Thompson and David Lee (2014)

The Cavaliers and Warriors wound up facing off in four consecutive NBA Finals, starting in 2015, but how different would those seasons have looked if this trade happened? It made sense at the time for Golden State, who had a certified young superstar in Stephen Curry, a young defensive anchor in Draymond Green, and a strong new coach in Steve Kerr. Thompson was still a bit of a question mark at the time, not yet the versatile, world destroying “Splash Brother” he would develop into in the ’14-’15 season. Love was a hot trade commodity in the summer of 2014, with the Timberwolves undergoing yet another rebuild and the All-Star making clear he wouldn’t re-sign with them in 2015. The Bulls, Knicks, and Celtics all made solid offers, while Golden State initially submitted Lee and Harrison Barnes. When Minnesota asked for Thompson instead of Barnes, the Warriors reportedly debated it but ultimately declined, opening it up for the Cavaliers to land Love instead.

18) Cavaliers trade Kyrie Irving to Suns, Pacers trade Paul George and Eric Bledsoe to Cavaliers, Suns trade first round pick to Pacers (2017)
19) Cavaliers trade Kyrie Irving to Bucks for Malcom Brogdon and Khris Middleton (2017)

When Irving made it clear that he was not interested in returning to Cleveland for the ’17-’18 season, the Cavaliers were flooded with offers for their All-Star guard. His eventual landing spot was Boston and the return for Cleveland was retrospectively poor, as a hobbled Isaiah Thomas barely contributed, the Cavs lost the 2018 NBA Finals in a sweep, and LeBron James left town for Los Angeles. Things may have gone completely different if they had instead pulled off one of the other two offers detailed above. Trading Irving (along with Channing Frye) to the Suns in a three-team deal with the Pacers would have landed them an All-Star in Paul George and a solid starting point guard in Eric Bledsoe. But when the Suns pulled out of the deal, it not only cost the Cavaliers those players, it also reportedly was the tipping point for Irving demanding a trade, as he believed James’ agent, who also represents Gordon, was orchestrating the move to push Irving out of Cleveland. Once the demand was made, the leading contender seemed to the Bucks, who were offering Brogdon, the reigning Rookie of the Year, and Middleton. Most experts agreed at the time that the trade package they received from Boston was superior but in hindsight there’s no doubt they were better off dealing with Milwaukee.