Chris Corlew
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Running a sports team is hard. Hell, running a fantasy football team is hard, not that you'll hear us ever admit it. The goal of every sports team is the win the championship and become friggin' legends, bro, but the goals of every front office is different from year to year. Sometimes it's a contending year, sometimes it's a rebuilding year, but always, the goal is an eventual championship. Unfortunately, winning it all is hard, and your very stupid screw-ups along the way are very public. Sometimes you screw up so much you get on a list like this:
Wikimedia Commons: UCLA digital library
It's maybe the biggest blunder in the history of sports (well, until we get to #1 on this list, but gotta start with a banger). Kareem Abdul-Jabbar, the third-greatest NBA player of all time, wanted to sign with the New York Nets out of college. Kareem was going to join the relatively new ABA, the NBA's flashier little brother. Commissioner George Mikan was going to offer Kareem $1 million on the spot, just for meeting with them. But Mikan, a “dumb SOB” according to subordinates, never gave Kareem the check. So Kareem went and won a championship in Milwaukee. Then five in Los Angeles. The Nets get to show up on this list again later. Without a championship.
Wikimedia Commons: Mack Male
Decades of box scores have documented the Chicago Bulls' failure to be halfway competitive since Michael Jordan's retirement; what doesn't get talked about (outside Bulls fans) is what an insular white boys' club the front office is. For years, decision-making positions and public-facing identity was led by John Paxson—a two-time Finals hero turned terrible GM—and a cadre of losers mostly associated with Iowa college basketball or personal friendships with owner Jerry Reinsdorf, like Tim Floyd, Gar Forman, and Doug Collins. Why they went that way instead of asking literally anybody else from the most globally popular basketball team ever remains a mystery.
This is less a management blunder and more a lament of the market forces of capitalism and the economic gravity of empire. Of course Wayne Gretzky wasn't going to stay in Edmonton his whole career, his dad knew that watching him hoist his fourth Stanley Cup. But still, what a tremendous loss for Canada, the country that makes hockey. Our hearts still go out to Oilers fans all these years later.
Wikimedia Commons: Keith Allison
Steve Kerr introduced Robert Sarver to the NBA. Turns out, that was a huge mistake, even if he doesn't think so. But his second-worst blunder on the Phoenix Suns was trading for 35-year-old Shaquille O'Neal, ending the exciting Seven Seconds Or Less Era and setting the Suns up for boring mediocrity at the end of Steve Nash's career (save for a fun 2010 conference finals run).
Wikimedia Commons: Keith Allison
Being an Orioles fan is hard. Team has real history—World Series-winning Brooks and Frank teams, the beloved Cal Ripken teams, that time Brady Anderson hit 50 homers outta nowhere—but Peter Angelos and his idiot sons act like broke boys. They probably never had a shot at re-signing Triple Crown threat Manny Machado, but the fact that they never really even tried is dog poop in the crab bushel.
Gail Goodrich was an NBA player who could shoot and that's about it. In 1975, the New Orleans Jazz wanted to sign 33-year-old Goodrich (he “wears his years well," coach Butch van Breda Kolff said, in an article that details coach's nine-hour pub crawl for his 54th birthday). As Bill Simmons points out, the Jazz had to renounce the rights to Moses Malone to get Goodrich. Any time you can have a past-his-prime white guy over a future MVP and champion, you gotta do it, right?
Wikimedia Commons: Keith Allison
A lot of digital ink has been spilled over Oklahoma City trading a future MVP for Jeremy Lamb and Kevin Martin (stash those names away for trivia night) that we don't need to rehash here. Bottom line: 10 years later, we can see that the Oklahoma City Thunder had three MVPs, never won a championship, and only made the Finals once. Bad times.
Sam Bowie over MJ. Darko over Melo, Wade, and Bosh. Jabari Parker over Joel Embiid. Derrick Williams over Klay Thompson or Kawhi Leonard. So many #2 draft picks are answers to trivia questions instead of All-Stars.
Wikimedia Commons: Keith Allison
Carmelo wanted to go to the Knicks. He would've signed there over the summer of 2011. Before he was a Knick, Carmelo was going to be a Knick. But lockout fears and James Dolan's impatience meant the Knicks traded half their team and all their depth to begin an ultimately doomed marriage.
The “not good enough” arguments fall apart when teams spent years signing 40-year-old has-beens and nepotism hires to pretend to play backup QB instead of Kaep. The “distraction” arguments fall apart when Deshaun Watson has a job and Kaep doesn't. Forget culture war BS, so many teams simply didn't sign a good quarterback.
Wikimedia Commons: Keith Allison
With the cultural cache of Watch The Throne-era Jay-Z and untold fortunes of new owner Mikhail Prokhorov, the New Jersey Nets moved to Brooklyn promising a title within five years. Bummer for Prokhorov's wild oats, turns out winning a championship's hard. The ill-fated trade of (checks notes) every single draft pick for aging stars Paul Pierce and Kevin Garnett didn't pan out, and Prokhorov sold the team before they even made a conference finals.
The 2011 Dallas Mavericks upset the Heatles Heat to finally win Dirk Nowitzki a championship. Instead of giving his team a chance to defend that title, Mark Cuban let the team fall apart. They had their eyes on superstars Dwight Howard and Deron Williams in free agency, but Deron & Dwight Do Dallas was not to be (Cuban even skipped the pitch meeting with Williams). The Mavs spent the next decade not winning playoff series.
Wikimedia Commons: Keith Allison
Yeah, Carlos Boozer stabbed them in the back. Sure, maybe LeBron phoned in the 2010 playoffs. But the bottom line is that the Cavs drafted the sure-thing greatest player of his generation in 2003, and the best player they could ever put next to him was Mo Williams. That team LeBron dragged to the 2007 Finals only to get embarrassed by the Spurs was a joke. LeBron's first run with the Cavs was organizational failure, no matter what Scott Raab says.
Wikimedia Commons: Erik Drost
“It's probably fair to say the Angels have wasted Mike Trout to the degree that has no precedent in any major sport," Baseball Prospectus wrote in 2016. The Ringer wondered if the Angels would stop wasting “the best baseball player on his generation” in 2017. That was before the Angels added Shohei Ohtani, a 46-homer, 156-strikeout two-way force unlike anyone we've seen since Babe Ruth. And, uh…yeah. The headlines about wasting talent haven't changed. This kind of management malpractice should really land people in The Hague.
Wikimedia Commons: Frances P. Burke
Maybe the most obvious and biggest blunder on this list. Greatest baseball player of his generation, the only guy who could pitch and hit at an elite level until Ohtani came around. Hope the $125k was worth it, Harry Frazee.
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