Anatomy of a Fleecing: How NBA Teams Make Bad Trades

As this goes to press, Twitter is exploding with news that the Milwaukee Bucks traded Eric Bledsoe, George Hill, and (get ready, folks) three first-round picks and two future pick swaps to the New Orleans Pelicans for Jrue Holiday.

The Bucks are in blatant win-now mode trying to put a Big Three together (and saying in no uncertain terms that Bledsoe is not a Big Three third guy) alongside two-time reigning MVP and 2020 Defensive Player of the Year Giannis Antetokounmpo and two-time All-Star Khris Middleton.

But in the process, they’ve pretty much told their fans “if Giannis leaves in free agency and we don’t win a title, get ready for at least a five-year stretch of suck that makes the mid-10s Brooklyn Nets look like the Showtime Lakers.”

This is a massive risk-reward play, but for possibly the first time in one of these sorts of deals, the team that acquired the metric ton of picks might actually be left holding the bag.

On the one hand, you’ve got the classic Brooklyn Fleecing (you’re welcome for the neologism), as perpetrated on the Nets by Danny Ainge in 2013. The Nets sent their 2014, 2016, and 2018 first-round picks (gods bless Ted Stepien) and a 2017 pick swap.

From that haul, the Celtics got Jaylen Brown and Jayson Tatum, then flipped the 2018 pick (Collin Sexton) to Cleveland for Kyrie Irving.

Yeah, they whiffed on the 2014 pick (James Young), but Young went 17th. Picks beyond the lottery are, ironically enough, lottery tickets in terms of their chances of winning something big. It seems there’s only one Giannis (15th in 2013), Pascal Siakam (27th in 2016), or Kawhi Leonard (15th in 2011) per draft, if that.

Speaking of Stepien, his generous willingness to get rid of draft picks is how the Lakers ended up with James Worthy in 1982. He also traded Cleveland’s picks in 1984 and 1986 to the Mavericks, who got Sam Perkins (a whiff by Dallas; they could’ve had Charles Barkley or John Stockton) and Roy Tarpley (in one of the worst drafts in NBA history.)

Cleveland picked first in the ’86 draft, because the NBA was so desperate to force a sale of the Cavaliers that they actually awarded new owner Gordon Gund picks that ended up being Charles Oakley, Brad Daugherty, and Kevin Johnson. The Cavs flipped Johnson for Larry Nance; they foolishly traded Oakley to Chicago for Keith Lee and Ennis Whatley. Imagine that late-80s Cavs team giving the Pistons and Bulls a run for their money over and above what the core they actually built got them.

Nobody’s giving the Bucks any first-round lottery picks if they screw up this trade.

As a bit of a tangent, the NFL saw this kind of nonsense in the 1980s and ’90s. There’s a reason you don’t see massive amounts of NFL draft picks traded for one guy anymore, and it’s a lesson basketball is going to learn the hard way if Milwaukee ends up as hot garbage and doesn’t get a title to show for it.

In 1989, the Dallas Cowboys shipped running back Herschel Walker to Minnesota; in exchange, they got draft picks that turned into Emmitt Smith, Russell Maryland, and Darren Woodson, powering their early-’90s dominance.

In 1999, the New Orleans Saints traded up with the Washington football team, sending their entire draft to DC for running back Ricky Williams, who was out of New Orleans in 2002 and for a time out of the league entirely because he preferred smoking marijuana to playing football.

The Saints trade wasn’t as one-sided as it at first appears, thanks mainly to Daniel Snyder having bought the Football Team—had Washington been competently managed, they might have built a dynasty with all of those picks, but they had to settle for 21 years and counting of being a garbage fire.

The point is that football teams don’t mortgage their future by trading truly ridiculous amounts of draft picks in order to win now.

The NBA has already seen this screw-up happen once; the Nets didn’t get good again until they did so the old-fashioned way and went through free agency to shore up a badly depleted roster of second-rounders and washouts; they got Kevin Durant and Irving and are rumored to be trying to pick up James Harden as the Houston Rockets’ ongoing 2020 offseason fire sale continues.

Milwaukee, in 2025, might be stuck doing the same—I wonder what Luka Doncic will be going for on the open market by then.

But we’ve got two sports’ worth of hard data to suggest that the Milwaukee Bucks just did something inexcusably stupid.

Football or basketball, you do not trade away your entire ability to stock your franchise with affordable young talent to win now. Too often, you don’t get the ring you wanted (the next time it happens will be the first), then your fans are subjected to years upon years of losing with no hope for the future.

Good luck with that, Bucks fans. Maybe it’ll work out for you.