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At first glance, a former great player becoming a front office executive or even a coach would seem like a no-brainer. Who better to assemble a championship-caliber roster than a person who experienced sustained success as a player? Who could run a franchise more effectively than a player who once carried it? But when looking at former greats who have transitioned from making plays on the court to executing deals in the front office, the results are varied.
Given Phil Jackson’s timely departure from the Knicks and Chauncey Billups’s pending deal to head the Cleveland Cavaliers’ front office, one question remains clear: Are the NBA’s GOATs equipped to handle the pressures of executive offices? Here's a look at the good, bad, and downright ugly.
The Good
Danny Ainge
Although he was more of a role player than his Hall of Fame teammate Larry Bird, Danny Ainge has transitioned well into the front office. The one time All-Star shooting guard did not find his footing as head coach during his failed stint with the Phoenix Suns, but he’s been the driving force behind Boston’s return to basketball glory in recent years. Since joining the Celtics as an executive in 2003, Ainge has developed a knack for negotiating deals to acquire major assets. His most notable haul involved assembling Boston’s “Big 3” in Paul Pierce, Kevin Garnet, and Ray Allen, which resulted in a 2008 NBA Championship and recognition as Executive of The Year. He also traded for star pint-sized guard Isaiah Thomas, signed utility bigman Al Horford, and hired Brad Stevens from the college ranks. Even now, the Celtics sit in a prime position to contend for the next few years with available cap space to sign a coveted free agent this summer—most likely (hopefully) Gordon Hayward—or trade for one with a stockpile of draft picks and assets. We will see if the Jimmy Butler trade that never happened comes back to bite him.
Jerry West
At this point, we might as well refer to Jerry West as a basketball god. Few people, if any, will ever be able to replicate his professional resume. As a player he experienced the pinnacle of success at every level imaginable. He was a highly coveted prospect out of high school, became a two-time All-American at West Virginia, and blossomed into one of the most influential players in league history. He's the goddamn logo of the NBA for crissakes. But for all of his accolades on the court, West has made an even bigger impact in the front office. He was the chief architect of the Lakers dynasty, from the Showtime Lake Show in the 1980s to the Kobe, Shaq, and Phil trio in the 2000s. He's also credited for resurrecting the Memphis Grizzlies to prominence, recently served as a special adviser to the Golden State Warriors, and currently holds a similar position with the LA Clippers. He has eight rings as an NBA executive. If there were ever a blueprint of how to transition from a Hall of Fame player to a Hall of Fame executive, West has it. He's got the keys.
Image via USA Today Sports/Trevor Ruszkowski
Larry Bird
Once a hallowed member of some of the Boston Celtics’ greatest teams, Bird was a beast on the court. The 6'9" forward from rural Indiana utilized his smooth shooting stroke, elite hustle, and uncanny consistency to excel as an all-around player both in college and the NBA. He garnered three league MVP trophies and led the Celtics to three NBA Championships over a superb 13-year NBA career. Five years following his retirement in 1992, Bird returned to his hometown Pacers as head coach and proved to be just as effective with a clipboard as he was on the court, taking Coach of the Year honors in 1998 and leading Reggie Miller and Co. to a 2000 Finals appearance. In recent years, Bird served as the Pacers president of basketball operations until stepping down this past season. He may not have any championships as an executive or a coach, but he's been influential in keeping the Pacers competitive for nearly a decade. If only LeBron James had played football instead of basketball, perhaps Bird might have some additional hardware in his decorated trophy closet.
Bill Russell
William Felton Russell knows a thing or two about “winning” basketball. After all, the Oakland native racked up five MVP Awards, 12 All-Star appearances, and 11 championship rings during his tenure in Boston, the most ever for a player. His presence is so profound throughout the league that the Finals MVP Trophy is in his namesake. But more impressive than his world-class rebounding, nimble passing skills, and tenacious defense, Bill Russell was known for possessing a remarkable basketball mind. During the final two years of his storied playing career, Russell succeeded Red Auerbach on the bench, becoming the first African-American to coach a professional sports team. He remains the gold standard for professionalism and excellence.
The Bad
Michael Jordan
Michael Jeffrey Jordan is widely regarded as the GOAT for a reason. Not only was he an assassin on the court, but he's also one of the most iconic professional athletes of all time and helped revolutionize the sneaker industry. We'll be wearing Jordan's Retros and debating whether anyone could ever live up to his Airness's accolades from now until the end of time. But despite Jordan's ruthless dominance as a player, his front office guru skills have left much to be desired. MJ began his executive career with the Washington Wizards, eagerly drafting one of the biggest busts in league history with the first overall pick in the 2002 draft, Kwame Brown.
Jordan later became a minority owner of the Charlotte Bobcats in 2004 (he is now majority owner, the first player to become such), and resurrected his career as a front office executive. However, the results weren't any better, as Jordan developed a penchant for drafting poor pro prospects. Here's a list of Charlotte's first-round picks under Mike's tutelage: Emeka Okafor (2004, 2nd overall), Raymond Felton (2005, 5th overall), Sean May (2005, 13th overall), Adam Morrison (2006, 3rd overall), Jared Dudley (2007, 22nd overall), D.J. Augustin (2008, 9th overall), Alexis Ajinca (2008, 20th overall), Gerald Henderson (2009, 12th overall), Kemba Walker (2011, 9th overall), Michael Kidd-Gilchrist (2012, 2nd overall), Cody Zeller (2013, 4th overall), and Frank Kaminsky (2015, 9th overall). That's 12 top 22 picks in 11 years with one All-Star appearance. One. (THANK GOODNESS FOR KEMBA WALKER!) Well, At least he's still selling out XIs every year on Black Friday!
The Ugly
Isiah Thomas
There's no denying Isiah Thomas's place as one of the best point guards the NBA has ever seen. Long before Stephen Curry, and the younger Isaiah Thomas who now plays for Detroit's vaunted rival, it was number 11 who utilized his dazzling speed to power the Pistons to back-to-back NBA championships. He was a giant killer on the court, serving as the floor general that commanded the Bad Boys to dismantle two dynasties (Bird's Celtics, and Magic's Lakers) before falling to His Airness.
But Thomas' tenure off the court has been mired in failure and controversy. Thomas began his post-playing career as president of basketball operations for the expansion Toronto Raptors in 1994. Although Zeke managed to draft some talented players in Damon Stoudamire, Marcus Camby, and Tracy McGrady, he ultimately left the franchise in a messy dispute regarding his role. Thomas then went on to coach the Indiana Pacers following Bird's retirement and an Eastern Conference title. The Pacers were loaded with young talent in Jermaine O'Neal, Brad Miller, Ron Artest, Al Harrington, and JamaalTinsley, with Reggie Miller serving as the wileyol' vet. But again, Thomas's arrogance and inexperience led to two consecutive first-round playoff exits.
Then there's New York. Not only did Thomas mortgage the Knicks’ future to acquire Eddie Curry, he also signed StephonMarbury to one of the worst contracts in the history of professional sports. Oh, let's not forget the sexual harassment debacle that resulted in $11.6 million being awarded to a female staffer. Thomas currently serves as president of basketball operations for the New York Liberty with his pal Bill Lambeer coaching on the bench. We'll let you know when this shit blows up.
Phil Jackson
Phil Jackson did the impossible. He’s the chief architect of one the league’s most signature offenses. He coached two of the game’s most iconic players—Michael Jordan and Kobe Bryant—during their respective reigns. He also found a way to make the NBA’s most dysfunctional franchise even worse. Eager to return the team he once suited up for back to prominence, Phil became the Knick’s president of basketball operations in 2014, and in his three years captaining James Dolan’s sinking ship, losing might be the best thing he’s accomplished.
Things were doomed from the start as Jackson fired Mike Woodson and his entire staff after a disappointing 2013-14 campaign. He then replaced Woodson with former point guard Derek Fisher, who was familiar with Jackson and his preferred style of play but had no prior coaching experience of any kind. That was followed by trading away Raymond Felton and Tyson Chandler for a pile of wet socks and two draft picks in the 2014 NBA draft—which he followed up by selecting more wet socks in Cleanthony Early and Thanasis Antetokounmpo. Jackson then proceeded to criticize, sign, and then criticize star forward Carmelo Anthony, and piss off the Knicks' only hope for the future, Kristaps Porzingis. Thankfully, Jackson’s no longer running things at Madison Square Garden. Let’s hope he never does anywhere else.