From Sam Bowie To Anthony Bennett: Here Are The Biggest Misses In NBA Draft History

sam bowie, kwame brown, anthony bennett
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The 2016 NBA Draft is nearly upon us, and though most accounts have Ben Simmons and Brandon Ingram as the jewels of this class and a tier above the rest, the one guarantee is that someone who’s widely considered a lesser pick will prove over the course of his career that he should have been selected a lot higher. For the players, being overlooked is often motivation to prove the doubters wrong, but for the teams, those mistakes represent brutal “what if” scenarios that change the course of history forever. Let’s look at 10 of the most regrettable oversights in draft history.

(NOTE: While there is considerable overlap here with the millions of draft bust lists out there, and necessarily so, these choices are made more for who teams didn’t select rather than who they did.)

1984: Portland Trail Blazers, Sam Bowie

The man from the crying face meme wasn’t the first or second pick of the 1984 Draft, but the third behind Hakeem Olajuwon (unimpeachable) and Sam Bowie. You can wonder why the Blazers drafted him — probably some combination of the league’s constant thirst for big men, and the presence of star Clyde Drexler at Michael Jordan’s position of shooting guard — but you will never wonder as much as Blazers fan do about the possibility of Michael Jordan going to Portland at No. 2.

1987: Los Angeles Clippers, Reggie Williams

The Dunbar high school star has never shown up on any all-time draft busts we’ve seen, because he was only the fourth pick and played 10 seasons with a couple of good ones thrown in. But he was a small forward, and a different small forward was picked one selection after, at fifth overall: Scottie Pippen, picked by the Seattle Supersonics (RIP) before being traded the same day to Chicago for a package centered around eighth pick Olden Polynice. Williams was an elite scorer for an elite college program in Georgetown while Pippen played for Central Arkansas, so the selection was defensible at the time. Looking back, though… yes. And it’s worth noting that self-important Bulls general manager Jerry Krause was super paranoid someone else would discover Pippen was so good and went out of his way to shroud his talent from other teams.

1995: Golden State Warriors, Joe Smith

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Of the first five picks in the 1995 Draft, four of them were power forwards. All of them would go on to have long careers, but Smith’s was significantly less distinguished than all the other three: Antonio McDyess, Rasheed Wallace and — most notably — Kevin Garnett. McDyess had a couple of 20-point, 10-rebound seasons for Denver before settling in as a useful role player later in his career following knee surgery that limited his athleticism; ‘Sheed was ‘Sheed, and KG is still KG. Joe Smith’s biggest NBA distinction was as one of the most traded players in league history. Not the kind of legacy the Warriors were envisioning.

2001: Washington Wizards, Kwame Brown

For my money, Kwame Brown is still quite possibly the biggest bust at No. 1 overall since the lottery began. His was another case of being the worst choice among a host of big men picked near the top of the draft, though one could go on about who was worse between him and Eddy Curry, taken fourth overall. But second and third were Tyson Chandler, an NBA champion and Defensive Player of the Year, and Pau Gasol, who won two titles with Kobe in Los Angeles, led some middling Grizzlies teams to the playoffs before being traded, and might wind up in the Hall of Fame when all is said and done. Meanwhile, Kwame provided the rare instance when a Stephen A. Smith rant was completely correct.

2003: Detroit Pistons, Darko Milicic

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Of all the teams picking in the top five of the 2003 Draft, the Pistons were an outlier. They were already a successful team that, thanks to a trade from six years prior, still lucked into the second overall pick. Sure, LeBron was always going first overall, but there was loads of other talent available. Perhaps, with a roster that would go on to win the NBA title the following season, the Pistons felt free to swing for the fences, but they popped out on a 3-0 count with the bases loaded and missed on (in order): Carmelo Anthony, Chris Bosh and Dwyane Wade. Think about the second life the Billups/Wallace/Wallace/Hamilton core could have had with one of those guys, and despair.

2006: Toronto Raptors, Andrea Bargnani

Bargnani’s selection at No. 1 overall is probably Dirk Nowitzki’s fault. The Raptors saw a 7-footer with three-point range and thought, “Hey, one of those just took a team to the NBA Finals! Let’s get him!” They simply overlooked things, like defense — just like Bargnani! Meanwhile, LaMarcus Aldridge has been one of the very best power forwards in the NBA since he was drafted. So what if he played the same position as Chris Bosh? It’s not like Bargnani was a rim protector or anything.

2008: Memphis Grizzlies, O.J. Mayo

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This is the first of two cases in a row when the Grizzlies whiffed on a superstar, in part because of the player they drafted in the lottery the year before. Mike Conley was their pick in 2007, so they went shooting guard in 2008 with the third overall pick. The thing is, Russell Westbrook was still on the board, and he wound up getting picked next. O.J. has bounced around the league and seems to have settled in as a decent shooter and role player. Meanwhile, Russ is a hellbeast who cannot be contained by humans. Shoring up all your positions is nice, but I’ll take the hellbeast, please and thank you.

2009: Memphis Grizzlies, Hasheem Thabeet

And of course, because of O.J., the Grizzlies didn’t consider James Harden, who was picked third after Thabeet was picked second. Thabeet never averaged more than the 3.1 points per game he did in his rookie season, which means a 7-foot-3 guy couldn’t figure out how to dunk the ball an average of twice per game (but it was really his defense and low basketball IQ that kept him off the court). The Grizz didn’t know what they had in a young Marc Gasol, who was already on the roster, but imagine if they had. Grit ‘n Grind sounds a lot different with James Harden to run the offense, doesn’t it?

2009: Minnesota Timberwolves, Ricky Rubio and Jonny Flynn

Wah wah.

How bad was this draft for Minnesota that one of the biggest busts ever at No. 2 is a footnote? The Timberwolves needed a point guard and had two picks in a row at five and six. So, OF COURSE David Kahn and company picked two point guards, neither of them being one Steph Curry, who went to Golden State seventh. Flynn and Rubio never played together, as Flynn flamed out amazingly quickly and Rubio took a couple years to get to the States. Though Rubio seems like a quite good point guard (jump shot notwithstanding), he’s not the back-to-back MVP. And, y’know, maybe they could have picked a point guard and someone else?

2013: Cleveland Cavaliers, Anthony Bennett

Some conspiracy theorists among us believe that the NBA knew how badly the Cavs screwed up this pick, so they gave them the first pick again (for the fourth time in 10 years) the next year for Andrew Wiggins (who would allow LeBron to return to Cleveland, setting up an incredibly lucrative redemption song — SEE?! YOU’LL ALL SEE!!). Bennett was such a strange pick that Bill Simmons lost it on the ESPN broadcast. You could make an argument that of all the players drafted in the first round — not just the lottery, the whole round — in 2013, Bennett was legitimately the worst of anyone who played NBA minutes. It was a notoriously talent-poor draft, out of which Giannis Antetokounmpo might wind up being the best player, but yeah, literally anybody else would have been a better choice. That doesn’t happen often!