1 of 14Kent Smith/NBAE via Getty Images, Manny Millan/SI
Arguably the game's greatest player, Jordan was anything but an MVP as a front-office leader. In a little more than a year as the Wizards' president of basketball operations, Jordan took a team that had gone 29-53 in the season of his arrival and rebuilt it into a 19-63 failure. After a short-lived comeback in uniform for two seasons, Jordan eventually made his way to the Bobcats' front office 2006 and then purchased majority ownership of the team in 2010. Under his leadership, the Bobcats have made it to the postseason just once, getting swept by the Magic in the first round in 2010, and are on pace to record the worst winning percentage in league history (1.06) this season.
2 of 14David Bergman/SI, Manny Millan/SI
After leading the Pistons to a pair of NBA titles, the 12-time All-Star enjoyed some modest success in building the Raptors before taking a sledgehammer to his executive career. In 1999, Thomas bought the Continental Basketball Association and led it to eventual bankruptcy before parachuting onto the Pacers bench as Indiana's new head coach. After guiding the Pacers to three playoff appearances, Thomas made his way to New York, where he oversaw a team that went 151-259 in his five years on the job.
3 of 14Greg Nelson/SI, Manny Millan/SI
A Hall of Famer and three-time NBA titlist with the Boston Celtics, McHale earned the ire of NBA fans across the league when he seemingly gift-wrapped the 2008 title for his former club by trading former MVP Kevin Garnett to Boston in the summer of 2007. That the Timberwolves were willing to peddle Garnett was also testament to McHale's mistakes in the Minnesota front office, from where he and the team had been stripped of three first-round draft picks after entering into an unsanctioned handshake agreement to retain one-time free agent Joe Smith in 2000. After a stint behind the camera as a TNT analyst, McHale accepted the head coaching job with the Rockets this summer.
4 of 14George Rose/Getty Images, Al Tielemans/SI
Millen, a four-time Super Bowl champion as a linebacker, failed miserably as a personnel man, leading the Lions to a 31-97 record from 2000 to `08 as the team's CEO/president. But Millen is far from the only athlete who had success on the field yet failed in the front office.
5 of 14David E. Klutho/SI, Robert Beck/SI
The NHL's all-time leading scorer has hardly been a Great One in the front office or behind the bench. During his eight seasons with the Phoenix Coyotes as managing partner, hockey operations director and coach, Gretzky has led the team to the playoffs only once. To his credit, Gretzky assembled the Team Canada squad that won the gold medal at the 2002 Winter Olympics, but his player talent pool was almost can't-miss.
6 of 14David E. Klutho/SI, Dave Sandford/Getty Images
One of the NHL's greatest goal-scorers (741; third all time), Hull washed out quickly as co-GM of the Dallas Stars. Upon being appointed to the role with Les Jackson in Nov. 2007, Hull's downfall was brought about by his insistence on signing notorious instigator Sean Avery, who proved to be a disruptive presence and was ultimately released during a 2008-09 season in which the Stars failed to make the playoffs for the first time in five seasons. In May, Hull was kicked upstairs to the title of Executive Vice President.
7 of 14V.J. Lovero/SI, John Iacono/SI
A World Series winner with the Yankees in 1978, and a big leaguer for nine seasons, Beattie was the Expos' GM from 1995 to 2001. Montreal posted losing seasons in all but one year of his tenure, which saw the Expos trade Pedro Martinez and acquire Hideki Irabu.
8 of 14 Vernon Biever/NBAE via Getty Images, Nathaniel Butler/NBAE via Getty Images
No one named one of the 50 greatest players in NBA history deserves this. But, hey, there are only so many NBA front-office jobs available, and only two in Los Angeles, where Baylor became the Lakers' all-time leading rebounder. Too bad Baylor found himself in the front office of L.A.'s "other" team. In 22 years leading the Clippers, Baylor watched the club reach the playoffs only four times, as opposed to the 14 seasons in which he guided the franchise to a 50-loss or more campaign.
9 of 14NBA Photos/ NBAE/Getty Images
The Knicks legend and NBA Hall of Famer was handed the front-office keys to the Nets' ship in 1988 and steered the club to a combined 257-399 record.
10 of 14Dick Raphael/SI
An All-Star in 1968, Hawk Harrelson played nine seasons in the Major Leagues, and eventually worked his way into the broadcast booth. Harrelson took a break from broadcasting in 1986, accepting the position of GM for the White Sox. During that time, he fired manager Tony LaRussa and assistant GM Dave Dombrowski, and traded rookie Bobby Bonilla (eventually a six-time All-Star) to the Pirates for Jose DeLeon.
11 of 14Andy Hayt/NBAE via Getty Images, Ron Koch/NBAE via Getty Images
The Hall of Fame center graduated to a front office career whose longevity stood in inverse proportion to its success. In Unseld's seven-year stint as Washington's GM, the club reached the playoffs once while averaging more than 53 losses a season.
12 of 14Heinz Kluetmeier/SI
An icon as Packers quarterback, Starr's success did not carry over to the personnel side. Green Bay hired Starr to be its head coach/GM in 1975 and stripped away his GM duties in 1982 after the Pack never had more than eight wins in a season during that stretch.
13 of 14Mark Kauffman/SI
Norm Van Brocklin
A Pro Football Hall of Famer as a quarterback and punter, Van Brocklin served as coach/GM for the expansion Atlanta Falcons from 1968 to `74. Though he did lead the Falcons to a 9-5 record in 1973, he was canned in 1974 after the team started 2-6.
14 of 14Herbert Weitman/WireImage.com
Wilson was a Hall of Fame safety for the St. Louis Cardinals, earning All-Pro honors eight times between 1960-72. After retiring, he worked his way up the organizational ladder and served as vice-president/GM from 1988 to `93, but the team never achieved a winning record during that span.
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