Scottie Pippen is undoubtedly the best sidekick in all of basketball. In his prime, the 6-foot-8 two-way superstar was good enough to be the number one option in any team in the league.
As seen in the recently concluded ESPN 10-part docuseries “The Last Dance”, Pippen’s tenure in The Windy City wasn’t always smooth sailing. The Hamburg, Arkansas-native had fought through contract disputes and feeling undervalued for much of his stay in Chicago.
Things have gotten so out of hand that then Bulls GM Jerry Krause tried to trade away Pippen on more than one occasion. Those deals, of course, never came to fruition, and Pippen became a vital contributor in the Bulls’ six NBA championships.
Still, it’s quite baffling to think that the team even considered shipping away their phenomenal winger. Here are five potential deals that the Bulls could have gotten for Pippen.
5. Los Angeles Clippers (1995)
The deal: It’s unclear what the exact offer was, but multiple first-round picks were discussed.
Details surrounding this mysterious deal were scarce considering it was just intriguing speculation back then. However, the Clippers did, in fact, had strong interest to make Pippen their franchise star and were reportedly willing to shell out multiple first-rounders to get him to LA.
According to Sam Smith in his book the “Second Coming,” Clippers executives Elgin Baylor and Andy Roeser pressed hard during the 1995 trade deadline for a deal for Pippen. Given the growing tensions between him and the Bulls brass, Pip actually entertained the idea of joining the disenchanted franchise at first.
Pip, however, was dissuaded by his teammate and former Clipper Ron Harper. The Bulls point guard was once quoted saying that his tenure in LA’s “other” team was like a jail sentence.
The Bulls and Clippers failed to reach an agreement minutes into the deadline and Pippen stayed in Chicago. Years later, Roeser confirmed the Pippen trade talks but claimed that no agreement was ever put in place. “I don’t think it was ever that close,” he said.
4. Phoenix Suns (1995)
The deal: Pippen for Dan Majerle, Wesley Person and two first-round picks.
Pippen and Charles Barkley eventually became teammates with the Houston Rockets in 1998-99 but it could have happened way sooner.
At a time when trade rumors continued to follow Pippen, the Suns reportedly tried to acquire him in a bid to return to the Finals. Pip even gave his thumbs up for the deal, describing Phoenix as a “paradise” destination to play in.
The deal centers around the Suns’ dependable swingman, Majerle. Granted that Pippen is overall the more superior player, Majerle was also a dependable defender and a better 3-point shooter. The Bulls also gets younger with the pair of first-rounders and an impressive rookie in Person.
The Bulls seemingly dodged a bullet on this one, as Majerle’s production dipped each year, while Person’s career was rather underwhelming.
3. Boston Celtics (1997)
The deal: Pippen and Luc Longley for two draft first-round picks (No. 3 and No. 6) or for the No. 3 pick and Antoine Walker.
Krause was indeed one busy man heading into the draft that year as he was orchestrating a possible deal with the C’s for their high draft picks.
Although Tim Duncan was the player everyone coveted in the draft that year, the Bulls would have been happy with a haul that could have resulted in the likes of either Keith Van Horn, Ron Mercer, and Tracy McGrady.
Boston even sweetened the pot by offering an alternate deal which includes sweet-shooting forward Antoine Walker. Had the deal been accepted by both parties, we could have McGrady and Walker in Bulls uniforms while Scottie would have pledged to the green.
Apart from losing Scottie, giving up Longley would have been quite a blow for the Bulls considering he gave them a huge boost on both ends of the floor. Although this could have prepared the Bulls in the second post-Jordan era, no doubt Chicago wouldn’t have completed its second three-peat had they pulled off this swap.
2. Toronto Raptors (1997)
The deal: Pippen for Tracy McGrady.
Jerry Krause’s never-ending quest to find the future of the Bulls (while neglecting the present team’s accomplishments) perhaps reached its peak when he intended to swap Pippen with a young high school phenom in Tracy McGrady. The Mount Zion Christian Academy standout, after all, was the same height and just as athletic (if not more) than Pippen.
Despite just winning their second consecutive title and 5th in franchise history, the Bulls were wary of their two superstars’ age. Jordan just turned 34 while Pippen was 32.
This trade was pretty much kept under wraps up until McGrady blew the whistle 13 years later on The Jump.
T-Mac recalled how Kraus even flew him to Chicago to do a physical and had discussions with team brass. That supposed draft-day trade never pushed through, and Toronto kept its 9th pick and selected McGrady.
No doubt the Raptors would have been the winners of this one had it gone through. While T-Mac eventually became a star, he would have trouble filling in Scottie’s shoes in his rookie year. Pippen, on the other hand, would have been surrounded by young talent in Vince Carter, Damon Stoudemire, and Marcus Camby in the upcoming years and could have been contenders in the East.
1. Seattle SuperSonics (1994)
The deal: Pippen, Will Perdue and the No. 21 overall pick in 1994 for Shawn Kemp, Ricky Pierce and the No. 11 overall pick).
Pippen could have very well played for the team that originally drafted him fifth overall in the 1987 draft. Krause always talked about rebuilding for the Bulls’ future and that was the perfect time to do so. Jordan just retired a year ago while Pip’s value was an all-time high following career-best averages across the board.
The 7-time All-Star also wanted a change in scenery, saying “I hope I am” when asked by the late Craig Sager about a potential trade.
In hindsight, the Sonics’ spread was quite enticing. Not only will Chicago get a mid-first round pick, but they will also get one of the most exciting power forwards in the league at the time in Shawn Kemp. Before weight issues grounded the 6-foot-10 rim-rocker, Kemp was an absolute destroyer and would have given the Bulls another fearsome interior presence.
Kemp could easily replace Purdue’s spot, while the Bulls will also get an experienced role player in Pierce. All signs pointed to the trade pushing through up until Seattle ultimately nixed the offer.