While he ended up a six-time NBA champion with the Chicago Bulls, Scottie Pippen was nearly traded from the Windy City numerous times.

Pippen was dealt to the Houston Rockets following Michael Jordan's second retirement in 1998, but the seven-time All-Star wanted out of Chicago two other times in his career.

Hindsight tells us that Pippen and Jordan were meant to be. They became one of the most dominant and successful duos in NBA history and needed each other to win those six titles.

But if the Bulls had pulled the trigger on a Pippen deal earlier, these are the best packages they would have received. All rankings are based on Chicago's potential to keep their dynasty going with Jordan, which would have been nearly impossible had they actually traded Pippen when he wanted out.

No. 4: Pippen Pairs with Charles Barkley in Phoenix; Dan Majerle to Bulls

Proposed Trade: Pippen to the Phoenix Suns for Dan Majerle, Wesley Person and two first-round picks in 1995

Before the trade deadline in 1995, Pippen was openly asking to be traded.

The Bulls were in their second year without Jordan and had a 23-25 record heading into the All-Star break. Pippen was the fifth-highest-paid player on the Chicago roster that season, making just $2.23 million despite finishing third in MVP voting the year before.

"Phoenix would be paradise," Pippen said at the time, per Michael Arace of the Hartford Courant. "It would be great. The Suns are a very competitive team. They're very experienced. It would be great for me. I'm hoping. I've heard every [rumor] from Milwaukee to Phoenix. I can see [the Suns] maybe pushing to make something happen. Charles [Barkley] isn't getting any younger. I can see them trying to push for a title."

Pippen even proposed a deal himself, something unheard of in today's NBA. His version had Majerle as the headliner, a three-time All-Star who had to dodge trade questions throughout the midseason break. Rookie Wesley Person and two first-round picks would be the sweeteners for Chicago.

While the Bulls were ultimately wise not to trade Pippen at all, this trade would have been a disaster.

Majerle was never the same following the 1994-95 season, averaging just 7.5 points on 39.3 percent shooting over the final seven years of his career. Person would go on to play 11 solid seasons in the NBA, averaging 11.2 points and 3.3 rebounds while shooting 41.8 percent from three but never making an All-Star team.

No. 3: Pippen Traded to Raptors for Tracy McGrady on Draft Night

Proposed Trade: Pippen to the Toronto Raptors for Tracy McGrady

Coming off a second straight championship and the fifth title in seven years for Chicago, general manager Jerry Krause was still eyeing the next era of Bulls basketball. 

Michael Jordan was 34 at the time, and Pippen was set to turn 32 a month before the start of the 1997-98 campaign. Pippen was also going into the last season of a seven-year, $18 million bargain contract and would certainly be seeking a raise.

McGrady was a high school phenomenon and a projected lottery pick out of Mount Zion Christian Academy as a 6'8" wing who could score, rebound and pass.

According to McGrady, Krause wanted him so badly that he flew him in right before the 1997 draft for a physical, willing to give up his current All-Star small forward in the process.

"The first thing that really stuck out to me, because I almost was a part of that, is 1997, Jerry Krause wanted to trade Scottie Pippen. It was said that if they went 82-0, no matter what, he was going to dismantle that team," McGrady said on ESPN's The Jump while reacting to the first two episodes of The Last Dance.

McGrady also stated that once Michael Jordan got wind of the trade, he "axed it," therefore keeping Pippen in Chicago for one more year. He never mentioned which team was willing to trade the pick used to select him, though the Raptors ultimately chose him at No. 9 overall.

Vince Carter was chosen fifth overall by Toronto a year later, winning Rookie of the Year and making the All-Star team by his second season. Although Carter's prime would come far later than Pippen's, the pair would have had a few successful seasons together in the late 1990s and early 2000s.

While McGrady would go on to make seven All-Star appearances and be inducted into the Hall of Fame, taking Pippen's place in 1997-98 would certainly have cost the Bulls their sixth championship and ruined Jordan's final season in Chicago.

No. 2: Pippen to Boston, Bulls Get Nos. 3 and 6 Overall Picks

Proposed Trade: Pippen and Luc Longley to the Boston Celtics for either the Nos. 3 and 6 overall picks in 1997 or the No. 3 overall pick and Antoine Walker

This trade could have gone a number of different ways.

Rick Pitino had just taken the Celtics' head-coaching job with the hope of drafting Tim Duncan first overall, and Boston had the best odds entering the lottery. The San Antonio Spurs ultimately landed the No. 1 pick, so Pitino was left searching for ways to acquire star players instead of bringing in two rookies with Boston’s third and sixth overall picks.

That's where Pippen came in.

The five-time champion had made seven of the past eight All-Star Games and was still playing at a high level heading into his age-32 season. He was the kind of star Pitino craved and needed to make the playoffs.

In a potential deal, Chicago could have acquired the two top-six picks and was eyeing Keith Van Horn, Ron Mercer and Tracy McGrady, per Sam Smith and Terry Armour of the Chicago Tribune.

There was also talk that Boston could have kept the sixth overall pick, sending second-year forward Antoine Walker (or third-year swingman Eric Williams) and the No. 3 overall pick to Chicago for Pippen and Longley.

While Duncan and Van Horn went Nos. 1 and 2, Chicago could have selected Chauncey Billups third overall (ultimately Boston's pick) and snagged McGrady at No. 6 (Boston took Mercer). Had Walker been substituted, he would have been a strong floor-spacer for Jordan. He made the 1997-98 All-Star Game while averaging 22.4 points, 10.2 rebounds, 3.3 assists and 1.7 steals for the Celtics.

Getting McGrady and Walker would have been the best possible long- and short-term option for Chicago, while Billups and McGrady would have completely rebooted the franchise at the cost of a sixth championship.

No. 1: Pippen Joins Gary Payton in Seattle; Shawn Kemp to Chicago

Proposed Trade: Pippen, Will Perdue and the No. 21 overall pick in 1994 to the Seattle SuperSonics for Shawn Kemp, Ricky Pierce and the No. 11 overall pick in 1994

This was the first major trade rumor involving Pippen to surface.

Michael Jordan had retired the year before (for the first time), and Pippen was the new face of a surprisingly competitive Bulls team that finished the 1993-94 season 55-27 before losing in seven games to the New York Knicks in the second round of the playoffs.

No longer looking like a title team without Jordan, the Bulls wanted to move Pippen while he was still in his prime. In 1993-94, Pippen finished third in MVP voting, trailing Hakeem Olajuwon and runner-up David Robinson while averaging 22.0 points, 8.7 rebounds, 5.6 assists and 2.9 steals.

Kemp was four years younger than Pippen, a high-flying power forward who was one of the most vicious dunkers of the decade. He had already made a pair of All-Star teams and put up 18.1 points, 10.8 rebounds, 1.8 steals and 2.1 blocks per game during the 1993-94 season.

Sonics head coach George Karl wanted to break up the duo of Kemp and Gary Payton, instead bringing in Pippen to form what would have been the best defensive duo in the NBA. And while Seattle ultimately killed the deal, this would have been the best offer for the Bulls.

Kemp and Jordan would have formed an incredible pairing. The athletic big man would go on to make four more All-Star teams and averaged 18.8 points, 10.0 rebounds, 1.3 steals and 1.3 blocks over the next six years.

While Jordan later told ESPN's J.A. Adande that he probably wouldn't have come out of retirement to play for the Bulls in 1995 had Pippen been traded for Kemp, this would have been the best non-rebuilding trade Chicago could have made.