Buying or Selling Biggest Gambles from 2020 NBA Offseason

Craig Mitchelldyer/Associated Press

Every offseason transaction is a bit of a gamble if you think about it. Changing an NBA roster, even in the smallest ways, takes it from a known to an unknown commodity. As much as we like to pretend we know how a new acquisition will work, it's impossible to be sure until seeing the fit on the floor.

And then there's the cost aspect.

The size of a gamble in the NBA roster-building context depends on the amount wagered—the contract awarded or the assets surrendered—and the downside risk. Bet big with a fat contract or an outlay of multiple picks, and that's a sizable gamble. Same goes for additions that eliminate future flexibility and/or expose the team to a scary worst-case scenario.

The phrase "nothing ventured, nothing gained" is a good one to keep in mind.

Here, we'll decide which big offseason gambles look like they'll be worth the trouble...and which ones already appear ill-fated.

Sue Ogrocki/Associated Press

It can be hard to resist analyzing NBA moves from a pure asset-accumulation standpoint. We agree first-round picks are valuable, sure, but their actual worth is still theoretical.

That's something to keep in mind as we survey the Oklahoma City Thunder's mountain of incoming picks—which grew significantly larger over the last few weeks as OKC tore its roster apart. No team has more than the Thunder's 22 first- and second-round selections coming in the next five years.

It's not quite right to say the hard work is still ahead, though there's no denying the Thunder have to turn those selections into something tangible—whether by using them to draft young talent or as trade chips to acquire more established players. OKC transacted with more than a third of the league's teams in a condensed offseason; it's remarkably difficult to operate with so many irons in the fire, and GM Sam Presti did it all without getting burned once.

Oklahoma City's strategy seems like the best one for a small-market team that wants a fresh start, and the first edition of The Process, which took place not so long ago in Philadelphia, proved you don't even have to get very many of those forthcoming draft decisions right to lock in several playoff seasons in a row.

The Thunder could have run it back—with Chris Paul or whatever more present-focused package he could have commanded in trade—and fought for a playoff spot. But Presti flipped the rebuild switch and positioned his team to win the longer game.

There's massive risk in swapping so many actual players for first-round picks with TBD value. We have to acknowledge the towering uncertainty ahead, even as we assert this gamble was one worth taking.

Verdict: Buy

Mark J. Terrill/Associated Press

If he's healthy, Gordon Hayward makes the Charlotte Hornets more likely to win basketball games. Nobody's disputing that.

To stick with the gambling conceit, the issue with Charlotte committing four years and $120 million to the 30-year-old forward is all about the odds. The Hornets seem to believe the payout—a slight improvement in short-term playoff probability and moderately heightened relevance—are worth the bet.

But that's like saying it makes sense to lay down $100 for a shaky shot at winning $10. That comparison is actually too simple, as it discounts concepts like opportunity cost. But you get the basic idea: Charlotte spent huge and waived Nicolas Batum as well, stretching his $27 million in dead money, for the privilege of paying Hayward $30 million per year. If everything breaks just right, the exchange might net the Hornets the eighth seed—which, now that the league has instituted a play-in tourney for the teams ranked 7-10 in each conference, doesn't even assure a playoff berth.

Hayward's injury history is a problem. As is Charlotte's decision to spend its cap space on a fringe All-Star (at best), rather than using it to absorb bad money with picks attached.

This is the kind of move only a desperate gambler would make.

Verdict: Sell

Stacy Bengs/Associated Press

Whether or not the Milwaukee Bucks had assurances from Giannis Antetokounmpo that a talent-boosting trade would up the odds of him signing a supermax extension, they really had no choice.

They had to sell off their down-the-road draft capital to improve the 2020-21 roster. That's all they did in acquiring Jrue Holiday from the New Orleans Pelicans for three first-round picks and swap rights on two more, by the way. Holiday can become a free agent after the upcoming season.

You wouldn't normally assume Milwaukee would make such a move without at least some idea about Holiday's willingness to stick around on his next deal, but when your organization's sole focus is showing Antetokounmpo you're serious about getting him a ring, you can worry about Holiday's uncertain future after getting that supermax signature from Giannis.

No hiding the ball here. The Bucks were wise to make this gamble. The sticker shock is real; Holiday is a fine player, but Milwaukee gave up a lot to get him. If Antetokounmpo doesn't sign or later decides to depart via trade demand, the Bucks won't have the draft picks they'll need to rebuild. They'll just lose a ton of games without the lottery upside to ease their pain.

Antetokounmpo is a generational player. Appeasing him is so singularly important to Milwaukee that even if the Pelicans had insisted on more draft assets for Holiday, the Bucks would have been justified in paying up.

Verdict: Buy

Ashley Landis/Associated Press

A $28.5 million trade exception is nothing to sneeze at. That's a multi-use tool that can be split up however the Boston Celtics see fit. If a mystery superstar (that makes $28.5 million or less) gets disgruntled during the year, the Celtics can swoop in with picks and that TPE to make a play for him.

Nonetheless, Boston may come to regret the other opportunity it passed up in the Gordon Hayward departure saga.

Indiana Pacers center Myles Turner, reportedly available in a sign-and-trade agreement for Hayward, would have been an ideal fit on Boston's front line. His mobility, stretch and rim protection would have opened up the Celtics offense to degrees heretofore unseen while also adding an element of interior defense Daniel Theis, bless him, can't match.

Turner is imperfect. He can't post up switches and struggles to rebound his position. But you don't expect perfection from a player making $18 million per season. That's "quality starter" money, and Turner is a quality starter—one who would have fit particularly in Boston.

Yes, that TPE gives the Celtics options. And if saving cash is a priority, they don't have to use it at all. But unless thriftiness was the sole motivation, it's hard to understand how Boston determined that Indy sign-and-trade was a worse return than a trade exception that might prove useful if the right circumstances arise at some point this season.

Boston is good enough to view itself as being one player away from a title. It's a stretch to say Turner is definitely that player, but there's a decent chance he is. Who knows what, if anything, will come from that TPE?

Verdict: Sell

Jeff Chiu/Associated Press

As physically impressive and undeniably talented as he may be, James Wiseman is still a center.

The league (Detroit Pistons notwithstanding) isn't big on those anymore, so the Golden State Warriors' decision to select Wiseman at No. 2 in the draft is absolutely a gamble.

Positional trends aside, the Wiseman pick was also a bold bet because Golden State could have traded the selection. That wouldn't have been at all surprising for a Warriors team trying to squeeze the most it can out of the end of Stephen Curry and Draymond Green's primes. For months leading up to the draft, speculation swirled around Golden State; it would have made perfect sense for the Dubs to package the No. 2 pick with Andrew Wiggins' salary, their $17.2 million TPE or even their highly valuable incoming Minnesota Timberwolves 2021 first-rounder (top-three protected).

The Wiseman pick looked a lot better after Golden State managed to use its TPE to get Kelly Oubre Jr. from the Oklahoma City Thunder without sacrificing any of its most valuable draft capital. For a while there, it seemed like the only way Golden State was going to extract value from that exception was by attaching it to the No. 2 pick. It turned out the Warriors didn't have to choose between Wiseman and help on the wing.

Optimistically, Wiseman will be serviceable at the 5 in his rookie season. The Warriors will limit his responsibilities to rim-rolling and shot-blocking at first. They'll play faster, which will make use of the center's uncommon open-court speed and fluidity. Maybe by the end of the year, he'll have shown enough growth to stretch the floor a bit or survive when switched onto guards. More likely, the defensive end will be a struggle, and Wiseman will vacate the center spot for Green in key moments.

Strange as it sounds given the Warriors' current position in the league, keeping Wiseman was the right gamble because it provides the franchise with a bridge to the future. The Warriors aren't true contenders, but there's a way for them to regain that status in a couple of years.

If Wiseman truly is a transformational talent who goes from just looking like David Robinson to playing like him, and if that Wolves pick nets the Dubs a second young cornerstone, well...we've got something that looks a little like the 2010s San Antonio Spurs.

Curry, Green and a hopefully healthy Klay Thompson would mirror Tim Duncan, Tony Parker and Manu Ginobili, while Wiseman and another young star would split the ascendent Kawhi Leonard role.

We're way into the weeds on this, and there are too many variables to count between now and the time Wiseman hits his stride. But because the Warriors couldn't realistically use the No. 2 pick to add a player capable of making them a contender in 2020-21, they were right to pursue a course that could get them back to that elite tier in a couple of years.

Verdict: Buy

Stats courtesy of NBA.com, Basketball Reference and Cleaning the Glass. Salary info via Basketball Insiders.