Wayback Wednesday: Where Legends Should Have Retired

This is Wayback Wednesday, your midweek blast from the past! From retrospectives of basketball games and their interesting features, to republished articles and looking at NBA history through the lens of the virtual hardwood, Wednesdays at the NLSC are for going back in time. This week, I’m reflecting on where a number of NBA Legends ideally should have retired.

With the 2026 NBA season underway, some of the biggest names in the league are continuing lengthy careers. LeBron James is embarking on a record-setting 23rd NBA campaign, which indeed may not be his last. Stephen Curry is in his 17th year, while former teammate Kevin Durant is in his 18th (though it would’ve been his 19th if not for missing the entire 2020 season). Of course, only Curry is still with the team that he began his NBA career with. As such, he’s the most likely of the three to retire with his original club, and having never left to boot.

Mind you, while it sometimes seems that superstars move around more often than they used to, even decades ago future Hall of Famers were wrapping up their storied careers on different teams. That’s how we’ve come to see so many familiar faces in strange places! To that end, while we focus on the accomplishments of those Legends and where they were in their prime more so than we do their weird final stints, we may still wish that they retired in the “right” place. Thanks to basketball video games, we can see what that would’ve looked like. Let’s take a look back…way back…

Michael Jordan: Chicago Bulls

I might as well begin with the most obvious example! Although I’ve come to better appreciate Michael Jordan’s Wizards years, my inner 90s child still wishes he’d only played for the Bulls. That would mean either remaining retired following The Last Dance, or making peace with being part of a rebuild and simply chasing the all-time scoring record. The latter was unlikely given his desire to compete for rings and a sour relationship with management that were set on blowing everything up. Returning alongside Scottie Pippen for a farewell tour is another option, albeit a highly unlikely one that wouldn’t be the same as going out on top. Still, MJ should’ve retired a Bull.

Dominique Wilkins: Atlanta Hawks

Funnily enough, this is actually the example that inspired this article! Dominique Wilkins’ final years in the league were single season tenures with different teams, alternating with his stints in Europe. He deserved better than that, and indeed that goes back to the Atlanta Hawks believing he was too old in 1994 when they traded him to the Los Angeles Clippers for Danny Manning. Granted, there’s no guarantee that Nique would’ve stayed in Atlanta right up until 1999, though if he did, it would’ve been a better send-off than warming the bench for the Orlando Magic. On the bright side, at least he finally returned to the Hawks in a front office role after he retired.

Shaquille O’Neal: Los Angeles Lakers or Miami Heat

See, this is where things get tricky! Obviously, the ship sailed on Shaquille O’Neal retiring in Orlando quite early. While he could’ve returned at the end of his career – and teamed up with Dwight Howard in the process – it wouldn’t mean as much as a return stint with the Los Angeles Lakers, or never leaving LA in the first place. The catch there is that once his feud with Kobe Bryant reached a breaking point in 2004, one of them clearly had to go! And so, if Shaq couldn’t realistically retire a Laker, his last stop should’ve been with the Heat. One good year in Phoenix aside, it was sad to watch him bounce around after leaving Miami, and truly bizarre to see him in Boston.

Moses Malone: Philadelphia 76ers or Houston Rockets

Despite being more nomadic compared to his generational peers, Moses Malone did have lengthy stints with the Houston Rockets and Philadelphia 76ers. And so, when he retired in 1995, it would’ve been cool to see him have one last run with either team. The Rockets are an interesting scenario because his longest tenure was with them, and he could’ve won another championship as Hakeem Olajuwon’s backup. On the other hand, he’s arguably better remembered for winning a title with the 76ers, and was also coming off a return stint with them in 1994. Joining the Rockets would’ve resulted in a grander farewell, but there would’ve been sentimentality in him retiring a 76er, too.

Patrick Ewing: New York Knicks

As much as having Patrick Ewing on the Seattle Supersonics and then the Orlando Magic made for some very interesting video game lineups, let’s face it: he absolutely should’ve retired a New York Knick! It’s what Ewing himself wanted, too. Granted, he ended up requesting a trade in 2000, but as Alonzo Mourning said when speaking on his friend and fellow Georgetown alum’s behalf, Ewing felt disrespected when the Knicks refused to sign him to an extension that’d take him through to the end of his career. At an impasse, the Knicks granted a request that it seems Ewing would’ve preferred not to make, meaning that one of their biggest Legends retired elsewhere.

Hakeem Olajuwon: Houston Rockets

Contrary to Patrick Ewing’s desire to remain in New York, his 1994 NBA Finals opponent Hakeem Olajuwon wanted out of Houston as his career was drawing to a close. With the Rockets entering a rebuilding phase and their contract offer of $13 million over three years not being to his satisfaction, The Dream preferred to move on. He found the Raptors and their three-year, $16.7 million offer appealing, and so was sent to Toronto in a sign-and-trade. Despite his excitement at the prospect of a fresh start, back injuries limited his minutes, and he retired at the end of the year. As such, I wish he’d remained a Rocket; a feeling former owner Leslie Alexander shares.

Karl Malone: Utah Jazz

Ideally, Karl Malone and John Stockton would’ve ridden off into the sunset together. It would’ve been a bittersweet ending – a first round defeat at the hands of the young Sacramento Kings – but it’d still be a fitting way to wrap up their careers. Of course, The Mailman wasn’t quite done yet, and decided to sign with the Lakers for one more shot at that elusive ring. Malone had demanded a trade a couple of times during his 18 years with the Jazz, so in retrospect it shouldn’t have been altogether shocking that he left Utah in the twilight of his career. At the same time, it was still a strange sight! As with the other 90s Legends who retired with another team, it just doesn’t feel right.

Mark Price: Cleveland Cavaliers

It’s understandable that the Cavaliers decided to move on from Mark Price in 1995. He’d definitely peaked, though more importantly he was beginning to become plagued by injuries. They also had Terrell Brandon ready to take over at point guard, though ironically Brandon would be traded in 1997, and retired young due to injury woes of his own. Nevertheless, much like Dominique Wilkins in Atlanta, it was a shame to see Price cast aside after a decade with the Cavs, and for someone who didn’t turn out to be a long-term replacement. Considering his two solid years with the Warriors and Magic, Price should’ve retired a Cavalier after transitioning to a bench role for them.

Nick Anderson: Orlando Magic

Let’s take a break from All-Stars and all-time greats to talk about team Legends! I recall an article about Nick Anderson signing an extension with Orlando in the 90s that described it as ensuring he’d be “a Magician for life”. As it turned out, they traded him to the Kings a couple of years later. Considering that he was the very first Draft selection in club history – not to mention still healthy, young, and productive – it was a shame to see. When you look at the way that the Oklahoma City Thunder kept Nick Collison and even retired his jersey, I think that Orlando should’ve done the same for Anderson. It does make you think twice about criticising players for a lack of loyalty!

Gary Payton: Seattle Supersonics

As you may know, Gary Payton played 999 games for the Seattle Supersonics before being traded at the deadline in 2003. Given that the split came about due to clashing with then-owner Howard Schultz, it’s a bitter footnote that makes the situation feel all the more petty. That’s not to absolve GP of all blame for the relationship souring, but at the end of the day, he should’ve retired a Supersonic. The Supersonics should also still be in the league, but that’s another topic entirely! I’m glad that Payton was able to get a ring with the Heat in 2006, but it’s still unfortunate that he was sent packing like that, and that the bad blood prevented a return stint before the team was relocated.

Shawn Kemp: Seattle Supersonics

While we’re on the subject of Gary Payton and the Sonics, fellow All-Star Shawn Kemp also should’ve hung up his Reeboks in Seattle. After a strong first year in Cleveland, The Reignman’s career went swiftly downhill. In all fairness, that may have happened anyway with the lockout and his substance abuse issues, and there’s a chance he was always destined to leave the team. I’d have loved to have seen Kemp and Payton have a much longer run together though, akin to John Stockton and Karl Malone. If nothing else, it would’ve been great to see them honoured with both of their jerseys retired in Seattle before the team became the Oklahoma City Thunder.

Chris Webber: Sacramento Kings

You can certainly argue this one, as it was cool to see Chris Webber retire after a brief return to the Warriors. It was a nice bookend to his career after abruptly leaving the team following his rookie campaign due to a feud with head coach Don Nelson. Still, Sacramento was where he finally established himself as a perennial All-Star, and he was healthy and playing well when they traded him in 2005. Hindsight is 20/20, but the Kings floundered and failed to rebuild after breaking up the core that almost made the NBA Finals in 2002. I’d suggest they may as well have kept C-Webb as their elder statesman star until he retired; assuming that he was just as keen to stay, of course.

Tim Hardaway: Miami Heat

It’s easy to forget that not only was Tim Hardaway still on the Heat in 2001, but that even though he was past his prime, he had a solid season as the team went 50-32. An injury late in the year limited his availability in the Playoffs however, and that was the beginning of the end; not just for his time in Miami, but in the NBA. Hardaway was still a capable player with the Mavericks and Nuggets in 2002 – an incident with a TV monitor aside – but retired in the offseason. He then had an optimistic but ultimately unsuccessful comeback with the Pacers in 2003. To that end, he might not have been able to keep playing until 2006 and win a ring, but he should’ve still retired in Miami.

Jason Kidd: Dallas Mavericks

Remember Jason Kidd’s final season with the New York Knicks? It’s understandable if you don’t, as it certainly didn’t end on a good note with Kidd failing to make a field goal in his final ten Playoff games. That’s not to say that he would’ve performed much better had stayed with the Mavericks in 2012, as he was already in decline. However, the sentimentality of finishing his career with the team that drafted him and he won a title with in 2011 after returning a few years earlier would’ve glossed over the fact he was running on fumes. Kidd’s decision to back out of a verbal agreement to stay with Dallas led to a falling out with Mark Cuban, but of course he’s now the Mavs’ coach.

Grant Hill: Orlando Magic or Detroit Pistons

It was only appropriate that co-1995 Rookies of the Year Grant Hill and Jason Kidd retired the same year. Like Mark Twain and Halley’s Comet, they came in together, and went out together! In Hill’s case, it was cool to see him revive his career after injuries in the early 2000s threatened to end it prematurely. It wasn’t as fun to see him warming the bench for the Clippers in his last year, though. He probably should’ve retired with the Suns, but I for one would’ve loved seeing him finish up in Orlando following a longer and more successful run there. Alternatively, I’d have enjoyed seeing him stay in Detroit rather than leave in 2000, or come back for his final season.

Rasheed Wallace: Detroit Pistons

Speaking of players that have a connection to Jason Kidd, Rasheed Wallace was also briefly on that 2013 Knicks squad. Sheed came out of retirement in 2012, having last played for the Celtics in 2010. Aside from the fact that his Boston stint almost netted him a second ring, Sheed ending his career with the Celtics or Knicks rather than the Pistons just doesn’t seem right. Considering that Chauncey Billups, Ben Wallace, and Tayshaun Prince all ended up returning to Detroit – though only Billups and Wallace finished their careers there – it’s unfortunate that Sheed didn’t, and that the starting five of the 2004 Championship team wasn’t ever able to reunite for one last run together.

Tracy McGrady: Houston Rockets or Orlando Magic

You can’t help but wonder how the early to mid 2000s might’ve gone down if Tracy McGrady and Grant Hill had actually been able to play significant minutes together. The possibility of Tim Duncan joining them in Orlando is naturally another massive “What If“, but T-Mac and Hill becoming the next great dynamic duo was obviously far closer to being a reality. McGrady’s years in Houston playing alongside Yao Ming were entertaining, albeit not as successful as fans hoped. I feel he should’ve retired with one of those clubs, rather than bouncing around in his final years. However, had the Spurs won it all in 2013, I’d nominate that as the ideal finale to T-Mac’s career!

Steve Nash: Phoenix Suns

One can’t blame Steve Nash for jumping at the opportunity to compete for a ring as his career was winding down. He was still playing at a high level too, so when he signed with the Lakers in 2013, it was a move intended to make them frontrunners for the title. Unfortunately, he suffered a leg fracture in the second game of the season, and with Kobe Bryant’s Achilles injury towards the end of the year, the 2013 Lakers ended up being one of the most underwhelming on-paper superteams in the history of the NBA. Again, hindsight is 20/20, but given his injury woes and the Lakers’ lack of success, it’d probably be a happier ending if Nash had just retired in Phoenix instead.

Tony Parker: San Antonio Spurs

Did the Spurs let Tony Parker walk to appease Kawhi Leonard, only for the move to come back to bite them when the latter demanded a trade? Seeing as how Leonard was sent to the Raptors before Parker even signed with the Hornets, I’d suggest there’s no truth to that. Moreover, the Spurs did try to re-sign Parker, but as he explained, he wanted to explore other opportunities in light of his reduced role on the team. Rather ironically, he ended up in a similar situation in Charlotte, and only played the first year of a two-year contract before retiring. Parker has since expressed regret that he didn’t retire a Spur, so I feel quite confident in saying that’s what should’ve happened!

Carmelo Anthony: New York Knicks

To state the obvious, Phil Jackson’s tenure in the Knicks’ front office was far less successful than his career on the sidelines. One of his biggest blunders was driving Carmelo Anthony out of town in 2017. Now, it’s true that the team only won one Playoff series during Melo’s time in the Big Apple, and there’s always a chance he would’ve demanded out and waived his no-trade clause at some point, even if he never butted heads with the Zen Master. Still, after so many other Knicks Legends retired in other clubs’ jerseys, the team should’ve sided with Melo with an eye to him finishing up in New York; especially since Jackson was let go that offseason anyway.

Paul Pierce: Boston Celtics

Technically speaking, Paul Pierce did retire as a Celtic. As more and more players seem to be doing in recent years, he signed a ceremonial contract with Boston in the 2017 offseason so that he could officially retire with them. Of course, he also poked fun at his departure in 2013 by wearing Brooklyn Nets shorts along with a Celtics t-shirt! Furthermore, considering his stated desire to retire a Celtic, it’s interesting that both sides never explored an actual return. I suppose the wounds were still fresh in 2014, and the Clippers were closer to home and a Playoff team when he joined them in 2015. Nevertheless, The Truth’s final game really should’ve been in Celtics green.

Amar’e Stoudemire: New York Knicks

Another player who ceremonially signed with a former club in order to officially retire with them is Amar’e Stoudemire. Although STAT continued to play overseas until 2020, he retired from the NBA in 2016 after spending his final season with the Heat. He’d left the Knicks a year earlier after they agreed to a buyout in the midst of an awful season, allowing him to latch on with the Playoff-bound Mavericks. In that respect, I guess Amar’e at least had a say in how his final seasons played out, but it would’ve been nice for his last NBA game to be with New York. A return to the Suns would’ve been cool too, but it does seem that he ultimately saw himself as a Knick.

Richard Hamilton: Detroit Pistons

I truly wanted to get excited about the Bulls signing Richard Hamilton in 2011. They were in need of scoring, and even at the end of his career, Rip remained a capable shooter. I also bore him no ill will, unlike fellow former Piston Ben Wallace! He was well past his prime though, making him yet another veteran star that the team picked up way too late. Obviously, Derrick Rose’s devastating knee injury was what really derailed the team’s promising future in the early 2010s, but Rip was never going to be enough at that point in his career. I don’t blame him for moving on, or the Bulls for taking a chance on him for that matter, but Rip really should’ve retired in Detroit.

Jermaine O’Neal: Indiana Pacers

I’ll admit that this one is a bit harder to argue. The Pacers parted ways with Jermaine O’Neal in 2008, following a season in which he missed 40 games and the team went 36-46. With JO in decline and having two years left on a big contract, it’s difficult to envision a scenario where he remains a Pacer right through to 2014. However, had he returned to the team in 2013 for one last run, he could’ve been a better backup to Roy Hibbert than Ian Mahinmi on a squad that was once again close to topping the Miami Heat. Of course, had he stuck around on the Warriors for one more year, he would’ve had a ring, but I respect his decision to step away to spend more time with his family.

Derrick Rose: Chicago Bulls

The idea of Derrick Rose “coming home” to finish his NBA career became something of a meme among Chicago Bulls fans. Truth to be told, it was definitely a suggestion inspired by sentiment rather than a belief that he’d make the team better. Mind you, I think they could’ve done (and did do) much worse than bringing him back in a bench role during his later years; at least while he was still relatively healthy and productive. In fact, I’ll still give in to sentimentality and say that his final year in 2024 should’ve been in a Bulls uniform, even if most of it was spent on the bench. I do understand ending his career with the Grizzlies though, bringing things full circle with Memphis.

A Few Thoughts on Storybook Endings

There’s a word I’ve used throughout this article: sentimentality. It’s the main reason that I and most other basketball fans would have preferred that Legends and other players who were important to their teams retired in the “right” place. Once again though, the fact that they retired in different jerseys or were far past their peak at the end of their illustrious careers doesn’t detract from what they accomplished in their prime. It could also be argued that we place too much importance on players spending their entire careers with one team. Plenty of all-time greats have switched teams, and there have been countless examples of clubs failing to reciprocate player loyalty, too.

However, to that point, it is still special to see players spend their whole career with a single club. It demonstrates tremendous loyalty on both sides, in a profession where that’s far from a guarantee. Similarly, it’s special when players who changed teams conclude their career on the one they’re most closely associated with. It allows that last season to be a celebration of their career, and wrap up with an emotional send-off. If a player’s final year allows them to have one more run that yields a championship, that’s even better. It’s why Michael Jordan’s Wizards comeback left many of us feeling so wistful. Hollywood couldn’t have scripted a more epic finale than The Last Dance!

Of course, sentimentality doesn’t define careers. We don’t rank David Robinson ahead of Michael Jordan or Kareem Abdul-Jabbar, just because his final NBA game was a championship-clinching contest and theirs were not. Hakeem Olajuwon’s later years and stint with the Raptors don’t place him behind Joel Embiid, though there are some younger fans and older contrarians who may try to argue otherwise. No one with any sense will claim that Shaquille O’Neal wasn’t one of the most dominant players we’ve ever seen just because he had a lacklustre, injury-plagued final year, or that he wasn’t a true franchise player because he moved around as his career was coming to an end.

Storybook endings make for entertaining narratives, but realistically, most Legends will retire without getting one…and that’s OK! That’s not to say that there isn’t any place for sentimentality in sports. The stories of triumph, heartbreak, and all sorts of fascinating journeys are what make basketball so fun to follow. Wondering “what if” and suggesting “what should’ve been” are all part of being a fan as well, which is why I set up these scenarios using video games. As long as we acknowledge that their weird stints and subpar twilight years ultimately don’t define their legacies, I believe it’s perfectly normal to wish that these Legends had retired in more fitting jerseys.

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