1) Tony Parker, Charlotte Hornets
Parker found himself at a crossroads with the Spurs in the summer of 2018. Tim Duncan had retired two years earlier and Manu Ginobili was now following him out the door. San Antonio’s all-time assists leader and 2007 Finals MVP, Parker was struggling after rupturing his quadriceps tendon during the 2017 playoffs. He posted career lows in scoring and assists in ’17-’18 and the always frank Gregg Popovich informed Parker that his role would be reduced. The former star point guard started exploring other options and found a friendly situation in Charlotte, where former Spurs assistant James Borrego had taken over as head coach. Though his numbers ticked up slightly from the previous season, Parker still struggled in ’18-’19 with injuries and increasing ineffectiveness. After 17 consecutive appearances with San Antonio, Parker missed the playoffs for the first time in his career and subsequently retired.
2) Shaquille O’Neal, Boston Celtics
After monumental, franchise-altering stints with the Magic, Lakers, and Heat, O’Neal surprisingly spent his twilight years as a mercenary. He was traded to the Suns in 2008, to the Cavaliers in 2009, then signed as a free agent with the Celtics in 2010. Shaq’s pairing with Boston was an irregular one from the beginning, starting with his awkward, self-applied “Big Shamrock” nickname. The 39-year-old O’Neal won the starting center job due to injuries to Jermaine O’Neal and Kendrick Perkins, and threw down a few vintage performances early in the season. But he struggled with leg soreness and knee pain, ultimately appearing in just 37 regular season games and two playoff tilts. After the Celtics lost a second round series against the Heat, O’Neal announced his retirement, citing a desire to no longer “hold Boston hostage.” In fairness to the Diesel, he did post respectable numbers for a big man his age and cost the Celtics less than $2 million for the year.
3) Rick Barry, Houston Rockets
So much had changed between Barry’s first departure from the Warriors in 1967 and his second a decade later. When he initially left Golden State, Barry shocked the basketball world by signing with the Oakland Oaks of the ABA to leverage against the lack of NBA free agency. He returned in 1972 and earned Finals MVP for the Warriors in 1975, but the team had fallen out of contention again by 1978. This time, Barry took advantage of the restricted free agency that now existed thanks to an Oscar Robertson lawsuit. He signed with the Rockets, who compensated the Warriors with John Lucas and cash. Barry’s two seasons with the Rockets were brief and relatively unmemorable, save for setting the NBA single season free throw percentage record in ’78-’79. Ever the malcontent, Barry would later call signing with the Rockets the biggest mistake of his career, referring to the franchise as a “zoo.”
4) Dominique Wilkins, Orlando Magic
He’s synonymous with Hawks basketball but Wilkins actually started his career with the Jazz and ended it with the Magic. Wilkins had no interest in playing for Utah after they drafted him third overall, forcing a trade to Atlanta. Over the next 11 seasons, he established himself as a Hawks franchise legend albeit with scant playoff success. As part of a rebuild, Atlanta traded Wilkins to the Clippers in 1994. From there, it was diminishing returns for the aging superstar, who struggled to contribute much for Los Angeles or in subsequent stints with the Celtics and Spurs. Wilkins was playing pro ball in Italy when the Magic signed him in 1998 at age 39. Orlando needed some veteran leadership and Wilkins took the opportunity to finally play alongside his his younger brother Gerald. Wilkins averaged just 5.0 points and 2.6 rebounds per game in one season with Orlando, then officially retired as the NBA’s eighth all-time leading scorer.
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5) Dave Cowens, Milwaukee Bucks
At age 31, the Celtics franchise legend Cowens theoretically could have continued on indefinitely as Bird’s teammate but was struggling with ankle and leg injuries. Cowens announced his retirement on the eve of the ’80-’81 season, ceremoniously handing over the reigns to Bird, who led the Celtics to a title that year. It was no big surprise to Celtics fans accustomed to Cowen’s capriciousness, which included a brief retirement in his prime to sell Christmas trees in Kentucky. Nor was anyone shocked when he announced a comeback two years later. The real bombshell though was Cowens asking for a trade and getting dealt to the Bucks. Playing under his former teammate Don Nelson, Cowens actually put in some solid contributions for Milwaukee as a backup center. But he suffered a leg injury in the regular season finale, leaving him sidelined for a second round series against the Celtics and forcing him to retire again, this time for good.
6) Hakeem Olajuwon, Toronto Raptors
7) Patrick Ewing, Orlando Magic
Two of the great paint warriors in NBA history, Ewing and Olajuwon are both indelible to the franchise that drafted them first overall. Ewing spent 15 seasons with the Knicks and is still the all-time franchise leader in games played, points, rebounds, blocks, and steals. Olajuwon put in 17 years with the Rockets, leading them to back-to-back titles in 1994 and 1995 while setting all the same franchise records that Ewing did. They matched up against each other in the 1994 NBA Finals, a terrific battle of two Hall of Fame bound centers in their prime. Their final matchup was a little less dramatic and in unfamiliar environs. In March 2002, Ewing finished with six points and five rebounds for the Magic, who defeated the Raptors and Olajuwon, who scored only two points. Ewing had joined Orlando as a free agent in 2001 while Olajuwon had been traded to Toronto. Both legends then retired in the subsequent offseason. Olajuwon did so after reportedly turning down a contract offer to return to Houston.
8) Alex English, Dallas Mavericks
Traded three times in his first four NBA seasons, English finally found a home in Denver. It was a match made in heaven in the Rockies, with English’s mid-range shooting and dribble-drives thriving in coach Doug Moe’s up-tempo system. He was the league’s overall leading scorer in the ’80s, named to eight All-Star Games, and led the Nuggets to nine consecutive playoff appearances. But that run did not include an NBA Finals appearance and the Nuggets opted to rebuild in 1990, firing Moe and letting English walk as a free agent. Upon signing a one-year contract with the Mavericks, the aging English announced that ’90-’91 would be his final season. He averaged just 7.6 points per game for Dallas and when they fell short of the playoffs, stayed true to his word and retired as the then seventh-highest scoring player in NBA history. The Nuggets retired his jersey soon after, and he still holds the franchise records for games played, points, field goals, and assists.
9) Walt Frazier, Cleveland Cavaliers
It must have been quite a culture shock for the effortlessly urbane Frazier, going from the culture hub of New York to the dying rust belt of late ’70s Cleveland. Over 10 legendary seasons with the Knicks, Frazier was the essence of NYC basketball on and off the court. He radiated cool with custom suits, a signature beige Rolls-Royce, and a steady presence in the night life scene. Frazier was also the heart-and-soul of two Knicks championship teams and the premier point guard of his era. But the Knicks started struggling in the wake of Willis Reed’s 1974 retirement and Frazier was shouldering the blame, especially after suffering a knee injury that sapped his athleticism. He was traded to the Cavs in 1977 in exchange for Jim Cleamons and made the best of it with his new lowly, far-flung franchise. Frazier’s stats declined sharply over the next couple seasons and he retired in 1980 to return to New York and become a broadcaster.
10) Michael Jordan, Washington Wizards
Here’s the thing about Jordan’s time with the Wizards: it’s not as bad as you remember. Despite carrying a little extra weight after three years away from basketball and playing with a subpar supporting cast, he managed to average a respectable 21.2 points, 5.9 rebounds, and 4.4 assists per game over two seasons. Washington improved by 18 wins in Jordan’s first season there, and came within a few games of reaching the playoffs in both campaigns. It’s also notable that his brief second comeback was a first opportunity for many fans to watch him play live, especially younger ones (and Spanish-speaking ones, as ESPN Deportes had been launched just before his return). But there’s no denying just how weird it was seeing Jordan in a non-Bulls uniform, especially one as tacky as what the Wizards were wearing in the early aughts.
11) Sidney Moncrief, Atlanta Hawks
After 10 seasons, two Defensive Player of the Year trophies, five All-Star nods, and three Conference Finals appearances, Moncrief still got a “what have you done for me lately?” response from the Bucks when his contract ended in 1989. Granted, the combo guard had struggled in his final three seasons in Milwaukee, dropping well off his typical career averages while suffering from the effects of a knee injury. With the Bucks moving on, Moncrief retired and purchased a car dealership back in his native Arkansas. A year later the Hawks, in need of some guard depth, called on the then 33-year-old Moncrief to return. He didn’t contribute much, averaging just 4.7 points in 15.2 minutes per game during the regular season, but his veteran leadership was immeasurable. Moncrief saved his best that season for nearly last, scoring 23 points in a shocking first round playoff upset win over the Pistons (Detroit put the series away one game later).
12) Dennis Rodman, Dallas Mavericks
Looking to make an immediate splash, new Mavericks owner Mark Cuban signed Rodman in 2000. Not only did he grant a contract to the outlandish 38-year-old who was a full year removed from his last NBA appearance, Cuban also let Rodman crash in his Dallas home. Sporting the jersey #70 and his hair dyed blue-and-yellow to match the team color scheme, Rodman lasted just 12 games in Dallas. He tallied double-digit rebounds in 10 of those games but also got ejected twice, suspended once, and essentially challenged David Stern to a naked boxing match. Maybe worst of all, the mercurial star seemingly had permission from Cuban to show up late to practices or even skip them outright. And how did he express gratitude for his new owner’s graciousness? By criticizing Cuban for his intrusiveness in player activities and overt chumminess with the roster and staff. This was likely the final straw, as Cuban (who later claimed it was unrelated) waived Rodman one day after those comments hit the media.
13) Dave Bing, Boston Celtics
In nine seasons with the Pistons team that drafted him and with which he’ll always be entwined, Bing had plenty of individual accolades but never any playoff success. Detroit reached the playoffs just three times in his nine years there, all first round losses. Bing was traded to a much better Bullets team in 1975 but they were soon stunned in the first round of the playoffs in 1976 and injuries started to hamper him. Thanks to years of carrying subpar Pistons squads, Bing was essentially damaged goods and signed with the Celtics on the cheap for the ’77-’78 season. He played much better in Boston than he had in Washington, but Bing was joining the Celtics just at the end of the Dave Cowens/John Havlicek title contending era and they missed the playoffs in 1978 for the first time in seven years (meanwhile, his former Bullets team won the title that spring). Upon retiring he returned to his adopted hometown of Detroit, eventually becoming mayor of the city in 2009.
14) George Gervin, Chicago Bulls
He was just two years removed from being a scoring champion and leading the team to the Conference Finals but the Spurs were ready to move on from Gervin in 1985 as part of a rebuild. The “Ice Man” was 32 years old with shaky knees but could still contribute and the Spurs traded him to the Bulls. This didn’t sit well with Chicago’s reigning Rookie of the Year Michael Jordan, who told the media he was “unhappy” about the transaction. Part of that was Jordan rejecting another prolific scorer on the roster but it was also related to Gervin being among the cadre of veterans who froze out Jordan in the 1985 All-Star Game. The trade turned out to be a blessing for the Bulls, who lost Jordan early in the season with a broken foot. Gervin averaged 17.8 points per game during Jordan’s lengthy absence, keeping the Bulls afloat and playoff bound. When Jordan returned, Gervin was suddenly buried on the depth chart, playing just 11 total minutes in the postseason to end his NBA career.
15) Karl Malone, Los Angeles Lakers
16) Steve Nash, Los Angeles Lakers
According to our metrics, Malone is the greatest player of all-time to never win a championship, while Nash is the second greatest to never reach the NBA Finals. Both made a late career push out to Los Angeles in an attempt to rectify their respective situations. Both were unsuccessful. Of the two, Malone was the much bigger disappointment as he joined an ’03-’04 Lakers team heavily favored to win the title. Malone looked decent enough at age 40 up until a knee injury sidelined him for 40 games and left him struggling in the playoffs. This was especially true in the NBA Finals upset loss to the Pistons, where Malone looked downright decrepit. Nash arrived in L.A. in 2012 alongside Dwight Howard, heralded as the last chance for Kobe Bryant to make a title run. But the two-time league MVP was a shell of his former self at age 38 and the Lakers stumbled into a first round series loss. Unlike Malone, who immediately retired after one season with the Lakers, Nash made one more go of it in ’13-’14 but played in just 15 games as they missed the playoffs entirely.
17) Moses Malone, San Antonio Spurs
Switching jerseys was no rare occurrence for Malone, who was on the roster of 10 different teams during his lengthy career. That included two different stints with the 76ers. One was in his prime during which he earned league MVP and Finals MVP in 1983. The other was at age 38 in ’93-’94, when Malone averaged career lows in scoring and rebounding but was at least queued up to retire as a 76er. Instead, he shockingly signed on for one more season but with the Spurs, for reasons still not fully understood. Fifth at the time in NBA history in scoring and third in rebounding, perhaps Malone was just looking to pad out those stats a little more and secure his place in history. He didn’t do much of that in San Antonio, making just 17 appearances and averaging 2.9 points and 2.7 rebounds per game. That final season did at least provide a memorable denouement moment for Malone, when he hit a buzzer-beating three-quarter-court shot to defeat the Hornets in his final game.
18) Robert Parish, Chicago Bulls
His most notable career moments all came alongside Celtics lifers Larry Bird and Kevin McHale but Parish both began and ended his career outside of Boston. He was drafted by the Warriors in 1976 and spent four seasons with the team before getting traded to the Celtics. Parish was three years older than Bird and four years older than McHale but far outlasted them both, playing to age 43 before retiring in 1997. Even at that advanced age, Parish was an asset for the Bulls in ’96-’97. He appeared in 43 regular season games, including three early season starts, as the Bulls cruised to a second straight title. It was a fourth career championship for Parish, who had previously earned three with the Celtics. Prior to his one season with Chicago, Parish also had a brief stint with the Hornets. It was mostly nondescript but did include him breaking Kareem Abdul-Jabbar’s record for career games played.
19) Gary Payton, Miami Heat
20) Clyde Drexler, Houston Rockets
As the SuperSonics slipped into mediocrity in the mid ’00s, Payton set off across the country to win his elusive first title. He made unsuccessful stops with the Bucks, Lakers (as Karl Malone’s teammate in ’03-’04), and Celtics before finally hitting pay dirt with the Heat. Payton was just two years removed from his last All-Star appearance when he signed with Miami in 2005, but his skill set was dipping precipitously at age 37. He still made some solid contributions, backing up Jason Williams as the Heat won a championship. Payton re-signed and played for one more season with Miami before retiring. Over a decade earlier, Drexler overcame the title-less fate that otherwise awaited contemporaries like Karl Malone and Charles Barkley. After 11 seasons with the Trail Blazers, he was traded at the deadline in 1995 to the defending champion Rockets. Still in his notional prime, Drexler averaged 21.0 points, 7.0 rebounds, and 5.0 assists per game as the Rockets repeated as champs. He spent three more seasons in Houston, making two more All-Star appearances, before retiring in 1998.
21) Paul Pierce, Los Angeles Clippers
Looking to make a splash under new owner Mikhail Prokhorov, the Nets traded for veterans Pierce and Kevin Garnett from the Celtics on the day of the 2013 NBA Draft. Despite spending his entire 15-year career up to that point with Boston, Pierce was at peace with the decision, claiming that a move to Brooklyn was his best chance to win another championship. It didn’t quite work out that way, as the Nets were bounced in the second round of the playoffs in 2014, and the same result ensued for Pierce on the Wizards in ’14-’15. Truthfully, he would have been much better off getting traded to the Heat in 2013 or signing with the Cavs in 2014 or 2015, but Pierce was likely much too stubborn to give in to playing alongside LeBron James. He made one last go of it by signing a two-year contract with the Clippers in 2015. Both of those seasons ended with the Clippers bowing out of the postseason first round and Pierce was waived. He then signed a ceremonial contract with Boston to officially retire as a Celtic.
22) Cliff Hagan, Dallas Chaparrals
With the NBA still hoarding the majority of talent, ABA franchises had to get creative in finding usable players. The two main options were drafting high-risk, high-reward phenoms, or giving veterans a chance to prolong their career. Hagan was the ultimate example of the latter, signing with the Dallas Chaparrals in 1967 at age 36. Hagan had spent his entire NBA career with the St. Louis Hawks, making five All-Star teams and winning a championship. But as the ’60s wore on, Hagan was phased out of the Hawks game plans and eventually retired in frustration in 1966. The Chapparals, a charter ABA franchise, brought him on as player-coach and it was mutually beneficial. Hagan revived his career, making an All-Star appearance and leading Dallas to the Division Finals. Hagan lasted three seasons in the ABA until achy knees and a fiery temperament caught up to him. He retired as a player in 1969 then stepped down as coach in 1970 to take over as athletic director at his alma mater Kentucky.
Next up in Bird and Magic
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