Michael Jordan retired from the NBA for the second time in 1999, seven months to the day after leading the Bulls to their sixth title in eight years. He cited mental fatigue and no longer having challenges within the game as two of his main reasons for calling it quits, but in the final episode of The Last Dance, Jordan admits he would have been willing to return to seek a seventh championship if the rest of his roster had come back with him. The echoes sentiments from the fourth episode. In February 1998, then-Bulls general manager Jerry Krause publicly announced that the Bulls would welcome Jordan back for the 1998-99 season, but not Phil Jackson, who was told before the season that the 1997-98 campaign would be his last run with the Bulls.

If he had it his way, Jordan may have had the opportunity -- with Jackson and Scottie Pippen by his side -- to defend their title until they were no longer champions. But after Jackson was not welcomed back, the Bulls began to rip apart the fabric of their championship roster. With his dreams of another title defense in Chicago dismantled, Jordan made good on his promise not to return to the Bulls and retired for the second time. 

But given his seeming preference to continue playing, where might Jordan have landed if he had explored free agency in earnest? Let's look around the NBA and find the five best fits for Jordan had he played during the 1998-99 season. But first, we need to establish a few caveats. 

  • Jordan would have to take a pay cut to play for another franchise. He earned over $33 million in his final season in Chicago, and considering the entire 1998-99 salary cap was $30 million, he just couldn't feasibly have made that much playing for any other team. Instead, we will base his salary off that of the NBA's highest-paid player that season: Patrick Ewing, who made $18.5 million. Jordan's pride would have demanded he be the highest-paid player in basketball, so we will set his salary for this exercise at $18,500,001. All salary figures used here will come from HoopsHype's database, but bear in mind, numbers that are two decades old are likely to be inexact. 
  • Jordan's salary would still represent over 61 percent of the salary cap at this figure. That would cost teams the modern equivalent of $67 million in cap space. Obviously, very few teams had the capacity to create such space, so instead, we will be dealing solely with sign-and-trade scenarios. Considering Chicago's lack of assets at the time, we will assume that the Bulls will play ball on any deal that does not leave them with a significantly negative value contract. The CBA signed during the 1998-99 lockout stipulated salaries match within 115 percent of one another in any trade, including sign-and-trades, so that is the framework we will work under. Retired players whose salary was still on their team's books in 1999 will be considered fair game. It should be noted that these trades are all fairly lopsided, but thanks to the looser guidelines regarding roster spots during the offseason, they are all manageable. Chicago would likely flip many of the assets acquired in these deals, but we don't need to dive into their machinations. 
  • Rosters will be reset to where they were immediately after the end of the lockout, when the Jordan sweepstakes would have begun, as Jordan's availability certainly would have influenced any suitor's decision-making. However, in cases where it makes sense, teams can still make moves that they made in reality. 

With those parameters set, let's dive in. 

5. Toronto Raptors

The sign-and-trade: Sharone Wright, Dee Brown, Doug Christie, Kevin Willis, B.J. Tyler and Chauncey Billups for Michael Jordan

Personal relationships would have driven this potential move. Just before the lockout began, Toronto acquired Jordan's close friend, Charles Oakley, in a trade with the Knicks. Their top draft pick was a fellow North Carolina alum, Vince Carter, and while Tracy McGrady didn't flash much as a rookie, Jordan at least had some familiarity after the Bulls nearly traded Scottie Pippen for him in 1997. The chance to improve his brand in an entirely new country in Canada likely would have appealed to him as well. The fact Isiah Thomas had just left his role running the team's basketball operations over a dispute with ownership wouldn't have hurt either. 

The real-life Raptors finished 23-27 during the 1998-99 season, missing out on the postseason by four games. Jordan almost certainly would have gotten them in, but their immediate prospects would have been limited with such a young and thin roster. Had Jordan stuck around to watch Carter and McGrady blossom, though, the sky would have been the limit. 

The Raptors didn't win their first championship until 2019, a full 25 years after being founded. Jordan's presence could have gotten them there nearly two decades sooner, potentially making them the fastest post-merger expansion team to hoist the trophy. 

4. Charlotte Hornets

The sign-and-trade: Anthony Mason, Bobby Phills and David Wesley for Michael Jordan. (Additionally, Charlotte would have had to have foregone its offseason signing of Derrick Coleman to make the move viable under the cap.)

Jordan's connection to his home state is well known. Not only did he attend the University of North Carolina, but currently owns these very Hornets. Even if the basketball situation isn't quite as enticing as some of the others, the temptation of home potentially could have lured Jordan back to Charlotte just as it eventually did to LeBron James in Cleveland. 

The roster here is admittedly underwhelming, though the cupboard isn't entirely bare. Star sharpshooter Glen Rice, coming off a 1998 All-Star appearance, would have been an excellent sidekick. Former teammate B.J. Armstrong was in place as well, though he was nearing the end of his career by this point. While much of Charlotte's veteran talent would be lost in this trade, a number of younger players on its roster would go on to meaningful NBA careers and could perhaps be rushed along. Brad Miller and Ricky Davis headline that list. 

Even still, this is the least-talented potential Jordan roster on this list. As they were, the '99 Hornets, after losing to Jordan's Bulls in the second round in the previous spring, would finish a game behind the Knicks for the final spot in the playoffs. With Jordan, the Hornets could have conceivably finished in the middle of in the East standings, and while a championship may not have been in the picture, his presence likely would have ensured at least a trip to the second round.

3. Miami Heat

The sign-and-trade: Tim Hardaway, P.J. Brown, Dan Majerle, Mark Strickland and Terry Mills for Michael Jordan

After coaching against Michael Jordan during the Bulls' legendary playoff matchups against the Knicks earlier in the decade, Pat Riley would have had the luxury of coaching Jordan, a player that shared his maniacal obsession with winning. Jordan never played with a center nearly as productive as Alonzo Mourning, and Jamal Mashburn was still in his prime as well. With 3-point marksman Voshon Lenard and veteran point guard Terry Porter in Miami as well, this would have been an extremely potent roster. 

The primary concern here would be depth, but thanks to the newly created mid-level exception, the Heat could have added at least one more weapon for their bench. Some notable options that made less than the $1.75 million Miami had to offer were shooting guard Dell Curry (who led the NBA in 3-point percentage that season), scoring wing Jim Jackson and forward Scott Burrell, a teammate of Jordan's during his final year in Chicago. In a fairly weak East, this roster should have been able to waltz to the Finals. Jordan should only improve a team that earned the No. 1 seed in reality with a 33-17 record. 

It's safe to say that the Heat, with Jordan replacing Hardaway, wouldn't have lost to the eighth-seeded Knicks in the playoffs. Beyond San Antonio in the Finals, it's hard to find a true challenger for such a balanced roster. In retirement, Jordan has settled in nearby Jupiter, Florida, only a 90-mile drive to Miami, so it's safe to say he enjoyed the region. Combine that with Riley's notorious aggression in roster building and this is a match made in heaven. 

2. Los Angeles Lakers

The sign-and-trade: Elden Campbell, Robert Horry, Travis Knight and Sean Rooks for Michael Jordan

A 61-win team during the 1997-98 campaign, the Lakers, led by Shaquille O'Neal and Kobe Bryant, fell to the Utah Jazz in the second round for a second consecutive postseason. Those struggles parallel those of Jordan's Bulls before their championship run, watching their season end at the hands of the Pistons three springs in a row before finally breaking through in 1991. 

While he was still the NBA's best player, Jordan had begun to show signs of fatigue during the '98 playoffs. Uniting with a 20-year-old Bryant, fresh off his first All-Star selection, would surely have helped him manage his workload, and while their skill sets certainly overlapped, the close bond the two formed in real life likely would have translated well in this scenario. If nothing else, they would respect each other's work ethic. 

Jordan never had the luxury of playing with a star center in Chicago, but O'Neal would have changed that. Shaq, who went on to win three consecutive Finals MVP awards, was at the peak of his powers entering the 1997-98 season. The trio of Jordan, Bryant and O'Neal almost certainly would have earned Jordan championship No. 7, and Nos. 8 and 9 would be in play as well. 

To cap it all off, the Lakers did sign Jordan's former teammate, Dennis Rodman, near the end of the '99 season. While Rodman ultimately flamed out in Los Angeles, Jordan's influence probably would have made a significant impact on Rodman. Surrounding the four of them would be a solid cast of role players: Eddie Jones (who isn't traded to Charlotte in this scenario, though perhaps could be flipped for another forward), Derek Fisher, Rick Fox and Derek Harper. If Jordan's sole goal was winning more championships, the Lakers would appear to be the front-runner here. 

1. New York Knicks

The sign-and-trade: Allan Houston, Chris Childs, Marcus Camby, Buck Williams and Charlie Ward for Michael Jordan

Sacrificing this much depth would have been problematic for a Knicks team that reached the NBA Finals without a true superstar in 1999. Ideally, they would have sent out Larry Johnson's bad contract in this deal, but Chicago would not have realistically taken it. Even without that depth, the Knicks would have complemented Jordan with Patrick Ewing, a teammate of Jordan's on the 1992 Dream Team and one of his closest friends in the NBA. 

While Johnson's contract may have been a long-term issue, he was in the midst of a career resurgence in New York and had arguably his greatest NBA moment during New York's 1999 title run with his famous four-point play against the Pacers. We'll assume that the Knicks still would have traded John Starks for Latrell Sprewell, giving Jordan another potent scorer to work with on the perimeter. 

The Knicks pursued Jordan in free agency in 1996 and very nearly landed him. It's not hard to see why. A union between the two sides would have been mutually beneficial. It's safe to say that, in terms of Jordan's legacy, helping bring the Knicks their first title in 26 years is the only thing that would have come close to capturing a seventh -- and fourth consecutive -- championship for the Bulls. The Knicks have not reached the Finals since that fateful 1999 season. If anything could enhance Jordan's already nearly infallible resume, it would be a championship in New York. 

Honorable mentions

San Antonio Spurs: An extremely tempting option based on their actual success in the 1998-99 NBA season, but hindsight is 20-20. While Jordan would have undoubtedly seen a talented roster here, even he likely assumed incumbent contenders like Utah and Indiana were better positioned to contend immediately. The market is likely also too small for Jordan's liking, and unlike most of the teams mentioned here, San Antonio might not be interested in trading half of its roster for Jordan. Such a move would seem uncharacteristic of Gregg Popovich. 

Portland Trail Blazers: Another contender on the rise, Portland had the contracts to trade for Jordan and the talent to win with him. But how would the notoriously competitive six-time champion feel about joining the team that infamously passed on him at No. 2 in the 1984 NBA Draft? Throw in a small market and the Blazers miss the cut. 

Houston Rockets: Scottie Pippen actually did land in Houston for the 1998-99 season, but there would have been no way to reunite him with his legendary teammate. The Rockets created the cap space they needed for Pippen by convincing Charles Barkley to accept a $1 million salary for this season, and even then they needed to deal Rodney Rogers to get him in the door. The Rockets just didn't have the salary to feasibly bring in both, and in any case, Jordan wasn't interested in playing with Barkley due to his poor work ethic. 

Philadelphia 76ers: Jordan has professed fondness for Allen Iverson in the past, and the two shared an agent in David Falk at the time. They just would have been horrible fits as teammates, as Iverson never played with a scorer remotely as gifted as Jordan. 

Utah Jazz/Indiana Pacers: Obvious candidates based on their place near the top of the 1999 pecking order, but Jordan simply seems too competitive to join a team he had just vanquished. Market size doesn't help either of their cases.  

Milwaukee Bucks/Washington Wizards: Jordan was hired as GM of the Wizards after his playing career ended, and he discussed a similar position with the Bucks at the time. Either could have potentially pursued him with the promise of a front-office position after his retirement. Such a scenario is fairly far-fetched, though, and not worth serious consideration.