Great players who became bad executives

Just how awful of an executive was Isiah Thomas, one of the greatest guards in NBA history? In May 2015, Rodger Sherman, then of SB Nation, explained why "hiring Isiah Thomas is the worst thing a basketball team can do." Tenures with the Toronto Raptors and New York Knicks, among other organizations, ended poorly, and the idea that a man accused of sexually harassing an employee, somebody who, as Howie Kussoy of the New York Post wrote, won over $11 million after filing a lawsuit, was given the privilege of running WNBA franchise the New York Liberty boggles the mind. For the benefit of all involved, Mr. Thomas, please stick to analyzing games on NBA TV. 

Norm Van Brocklin was one of the greatest pro quarterbacks of the 1950s, a nine-time Pro Bowl selection who won a pair of championships and earned MVP honors in 1960. From 1970 through 1974, he served as both head coach and general manager of the Atlanta Falcons, but only two winning seasons in five years and a lousy '74 campaign ultimately cost him the job. The outspoken "Dutchman" wasn't particularly popular among those he coached, per Dave Mangels of Bleeding Green Nation: "As a coach, the qualities that made him a great player didn’t apply, but the qualities that made him despised by some of his teammates made him hated by practically all his players. The intensity that drove him to success on the field made him a tyrant on the sidelines."

Hall of Famer Brett Hull twice won the Stanley Cup, and he scored one of the most controversial title-clinching goals in modern history. Hull already had a role with the Dallas Stars in the fall of 2007 when the club promoted him to interim co-general manager, and Dallas reached the 2008 conference final. Things went downhill from there. The Stars signed Sean Avery in one of the worst acquisitions in league history, and the team's failure to make the postseason the subsequent spring cost Hull and Les Jackson their gigs as co-GMs in May 2009.

Kevin McHale was a three-time champion worthy of the Hall of Fame and also a decent head coach. It's as an executive, though, where he came up short. The Minnesota Timberwolves named McHale general manager in 1995, and the hiring of Flip Saunders coupled with drafting Kevin Garnett seemed to indicate Minnesota was headed in the right direction. Trading Ray Allen, one of the greatest shooters in history, for Stephon Marbury the following year proved costly for McHale, as did the Joe Smith contract plan. ESPN.com offered the following after McHale's time with Minnesota concluded in June 2009: "There was McHale the gifted teacher, beloved by players and staff for his relentlessly positive demeanor and an unending eagerness to share his wealth of basketball knowledge. Then there was McHale the mistake-prone executive, vilified by fans for a series of blunders and the failure to make his team into a consistent championship contender."

Two-time All-Star Billy Knight remains the third all-time leading scorer in the history of the Indiana Pacers. The Atlanta Hawks promoted Knight to general manager in 2003, and following a lengthy postseason drought he piloted the club to the playoffs in the spring of 2008. Unfortunately his bad draft decisions hovered over the franchise until he and the Hawks parted ways in the summer of '08. He drafted Marvin Williams when Chris Paul was available in 2005, and the Hawks selected bust Shelden Williams the following year. 

Charlie Gehringer was a member of the 1935 Detroit Tigers that won the World Series, and he earned American League MVP honors after taking the batting title that season. Per the Chicago Tribune, Gehringer served as the franchise's general manager from 1951 through 1953, and the Tigers posted losing records in all three of those seasons. “I did not enjoy it. I had been away for nearly 10 years and I didn't know the leagues. I was more or less forced into it," Gehringer later said of the job, per Ruth Sadler of the Society for American Baseball Research.

Doc Rivers will likely do just fine as a coach as long as he lets somebody else make the decisions behind the scenes. The 57-year-old one-time All-Star worked as both head coach and vice president of basketball operations for the Los Angeles Clippers from 2013 through 2017 until he was demoted to just coach, and while the Clippers have remained playoff mainstays, they haven't yet taken the figurative next step toward a title. In August 2017, the SB Nation NBA staff posted a history of what it called Rivers' "uncreative and lackluster" job as an executive. 

Manchester United phenom Sir Bobby Charlton is one of the world's greatest-ever footballers and the man who won the 1966 Ballon d'Or. In 1976 Charlton took over as a director at Wigan Athletic, per The Telegraph's Robert Philip, and the club was welcomed into the Football League in 1978. By 1984, though, Charlton returned to United as an ambassador and director. He never again accepted a major role with a different club. 

Long before he was talking about NHL games on NBC Sports, Mike Milbury spent 12 years with the Boston Bruins, and he was part of the Boston rosters that lost the 1977 and 1978 Stanley Cup Final series to the Montreal Canadians. In 1995 the New York Islanders named Milbury, already the team's coach, general manager, and, well, let's just say he disappointed in the role through 2006. In 2010, Bleacher Report's Bradley Karp listed five mistakes credited to Milbury. Not to be outdone, The Hockey Writers recalled 10 Milbury blunders in February 2017. 

Still respected as one of basketball's all-time greats, Elgin Baylor made 11 All-Star teams from 1959 through 1970. He also won NBA Executive of the Year in 2006. How, then, did Baylor land here? As ESPN's Kevin Arnovitz wrote in 2009, Baylor worked as vice president of basketball operations for the Los Angeles Clippers from 1986 through the fall of 2008, and, per Arizona Sports, the Clippers suffered through 20 losing seasons and tallied an overall record of 607-1153 during his time as a team executive. From Arnovitz: "However you grade his performance, Baylor will likely go down simultaneously as one of the most enduring — and least notable — executives in the history of sports." The harsh reality is Baylor became synonymous with one of the most dysfunctional organizations in North American pro sports. 

Depending on your age, you know Ken "Hawk" Harrelson as the one-time All-Star who led the American League in RBI in 1968, a commentator for the Chicago White Sox for over three decades or a combination of the two. Per Rob Ogden of the Chicago Sun-Times, Harrelson called the MLB general manager position "the worst job in baseball" in 2016. It's easy to understand why he'd feel so passionately about the matter. Back in 1986, his one and only year spent as White Sox GM, Harrelson fired Tony La Russa, a decision for which he labeled himself a "fool" in 2014, as ESPN's Doug Padilla wrote. Harrelson also traded Bobby Bonilla, who became a six-time All-Star, before quitting that September. 

As time goes on, history likely will forget Hall of Famer Joe Cronin was one of the finest shortstops of his era and a seven-time All-Star. Instead, the man who took over as Boston Red Sox general manager in 1947 is viewed as a reason the franchise failed to racially integrate the roster, and for why a team that lost the 1946 World Series failed to make the postseason up through and past Cronin's last year on the job in 1958, per Mark Armour of the Society For American Baseball Research. According to ESPN's Gordon Edes, Cronin once passed on Willie Mays. 

Just the mention of Jim Paxson's name sends shivers down the spines of Cleveland Cavaliers fans. The two-time All-Star was already with the Cavs when he became team general manager in June 1999, and Cleveland accumulated a record of 185-307, per the Associated Press (h/t ESPN), until the franchise fired Paxson in April 2005. At least he knew to tank so the Cavs could draft LeBron James in 2003.

We keep it in the Paxson family to focus on one half of the #FireGarPax social media movement mentioned by fans of the Chicago Bulls on a daily basis. John Paxson won three rings as a player with the Chicago dynasty of the 1990s, and it's not the fault of the executive who has been with the organization since 2003 that Derrick Rose's body betrayed him. As Ricky O'Donnell of Blog A Bull has written multiple times, Paxson, still the team's vice president of basketball operations, hasn't offered much evidence that he has the answers to right the ship. Recently, Patrick Sheldon of Da Windy City suggested even the Bulls don't trust the club's current rebuilding process. 

Hall of Famer and five-time All-Star Chris Mullin unquestionably deserves credit for building the Golden State Warriors roster that stunned the Dallas Mavericks in the opening round of the 2007 postseason for what NBA.com referred to as "maybe the greatest playoff upset in NBA history." The one-off of a No.8 seed toppling the conference's best regular-season side wasn't enough for Mullin to keep his job for long. Losing Baron Davis to free agency in the summer of 2008 along with other poor decisions and the Warriors falling in the standings resulted in the club choosing a different direction in 2009.

As the Telegraph's Luke Edwards humorously pointed out in July 2013, Joe Kinnear wasn't always the most truthful individual during his stint as Newcastle United director of football, but Kinnear did win the FA Cup, League Cup and UEFA Cup while playing for Tottenham Hotspur. He announced he'd accepted the role at Newcastle in June 2013 but resigned the following February after a pair of disappointing transfer windows. Soon after Kinnear's departure, Metro's Paul Mannion wondered if Kinnear was ""the worst director of football in history:" 

"From the minute Kinnear announced his return on national radio, abusing the club’s fan base and continuing his trend to confuse players name, he has been nothing but an embarrassment. It’s been two transfer windows since he claimed ‘judge me on my signings’ but no player ever put pen to paper on a permanent deal. Who can blame them. [sic]"

Hall of Famer Wes Unseld was named Rookie of the Year and Most Valuable Player for the 1968-69 season, and the five-time All-Star earned MVP honors for his play in the 1978 NBA Finals. In 1996 he became general manager of the then-named Washington Bullets, and the team made the playoffs that season. Then came curious decisions, like trading Chris Webber for Mitch Richmond and Otis Thorpe and dealing Ben Wallace for Isaac Austin. His run as Washington general manager ended in 2003.

Elected into the Pro Football Hall of Fame in 1978, safety Larry Wilson made eight Pro Bowl squads during his career that spanned from 1960 through 1972, and he was First-Team All-Pro every year from 1966 through 1970. Per Pro-Football-Reference, he spent 14 seasons as director of pro personnel and, later, general manager and vice president with the Cardinals franchise. The club made one playoff appearance over that time. As explained by the Associated Press (h/t Huron Daily Tribune), he oversaw "Cardinals Charities, special events, team travel and training camp at Northern Arizona University in Flagstaff" after serving as GM until he retired in April 2003.

We'll always remember Willis Reed as a two-time NBA champion and, of course, for that one iconic on-the-court appearance. After coaching the New Jersey Nets for a couple of seasons, Reed accepted a front office role with the organization following the 1988-89 campaign, and his Nets made the playoffs every year from 1992 through 1994. The shine quickly disappeared from the apple, though, and he was moved to senior vice president of basketball operations in 1996. 

Bart Starr will forever be a legend as long as the Green Bay Packers and pro football exist, but the Hall of Famer and two-time Super Bowl MVP made for one lousy general manager. Along with accumulating a losing record during a dark period for the storied franchise, Starr's Packers suffered a different type of humiliation when defensive tackle Bruce Clark, selected fourth overall in the 1980 NFL Draft, opted to play in Canada rather than for Green Bay. The club dismissed Starr in December 1983. 

All Magic Johnson, a five-time champion player and arguably the greatest point guard and all-around player in history, had to do as Los Angeles Lakers president of basketball operations, a job he earned in 2017, was surround LeBron James with enough talent to qualify for the postseason after King James took his talents from the Cleveland Cavaliers to the West Coast in the summer of 2018. Yes, James dealt with injury woes throughout his first not-so-Showtime campaign, but Johnson's failures to acquire Anthony Davis or any other noteworthy player ahead of the February trade deadline ultimately sank the Lakers and his tenure with the organization. Last April, Chris Herring of FiveThirtyEight explained why he believed Magic was never the right man for the job.

As Clark Spencer and Barry Jackson of the Miami Herald wrote, Derek Jeter earned the right to become an owner and also the chief executive officer of the Miami Marlins in September 2017, so it's early days into this experiment. Many have, however, been left unimpressed since that time. Luther Campbell of the Miami New Times called Jeter "worse than Jeffrey Loria as Marlins owner" in October 2018 following the ousters of stars Christian Yelich and Giancarlo Stanton, and dealing J.T. Realmuto to division rivals the Philadelphia Phillies also didn't sit well with members of the fan base. As of June 26, the Marlins were well in last place in the NL East. 

You don't have to be some hockey expert to know Wayne Gretzky is the sport's greatest player. Arguing the point is silly. Similar to Mario Lemieux, who prevented the Pittsburgh Penguins from relocating to Kansas City, Gretzky officially became a managing partner with the Phoenix Coyotes in 2001, as Michael Farber of Sports Illustrated wrote, in part to keep the financially struggling team from potentially moving. "The Great One" appointed himself coach ahead of the 2005-06 season, and he tallied a record of 143-161-24 over four years before parting ways with the organization. 

"My brother is a lions [sic] fan, and we aren’t allowed to say Matt Millen’s name inside the house." "Legit exactly the same with my uncle. He immediately starts cussing about it and gets super sour. Anytime Millen is mentioned or on screen he goes and mows his lawn in a fit." Those are just a couple of Reddit endorsements regarding former Detroit Lions team president and general manager Matt Millen. The four-time Super Bowl champion as a player is widely regarded as one of the worst executives in the history of North American pro sports, a man who sank the Detroit Lions to an overall record of 31-97 from 2001 through 2008, since Pro-Football-Reference "credits" him with Detroit's 0-16 2008 season even though he was fired in September of that year. Just search "Matt Millen worst GM," and you'll come upon literally hours of reading material. 

Michael Jordan may be the G.O.A.T. player (debate on your own time), but his executive skills haven't led the Charlotte Hornets to anything resembling the success His Airness enjoyed with the Chicago Bulls. M.J. became a part owner of what was then known as the Charlotte Bobcats in 2006, per NBA.com, and the organization has made only three playoff appearances since 2010 under the club's current majority owner. The draft mistakes over the past 13 years stand out in a big way. Adam Morrison in 2006. D. J. Augustin in 2008. Gerald Henderson in 2009. Michael Kidd-Gilchrist instead of Bradley Beal or Damian Lillard, among others. Malik Monk over Donovan Mitchell?!? Ouch.