NBA front offices have gotten so smart. Every year it feels like we see fewer and fewer questionable decisions. Free-agent signings. Contract extensions. Trades. Draft picks. Information is everywhere, everyone is so careful, and yet, at the end of the day, everything is still a gamble. Here are four offseason moves that feel like a pretty big roll of the dice. 

Warriors trade for D'Angelo Russell

There's an obvious school of thought that if you're the Warriors, and you're going to lose Kevin Durant for nothing with no realistic way of replacing him, then any player you get in return should be considered a bonus. If that player is a 23-year-old All-Star, as D'Angelo Russell is, then you would, by this school of thought, have turned undrinkable water into fine Italian wine.

There is truth in this. The Warriors were going to lose Durant for nothing, and looking forward, they didn't -- and still don't -- project to have any cap room for the foreseeable future, let alone enough to even broach the possibility of halfway replacing Durant. At some point, they were going to have to get creative. 

A last-minute sign-and-trade, Durant for Russell, is definitely creative. 

But Russell wasn't a pure bonus. He cost. A lot. For starters, the Warriors had to ship out Andre Iguodala to fit Russell's money below the hard cap the trade triggered, and while that could be seen as an organization getting ahead of the curve on an aging, relatively expensive player, if you're going into a playoff series tomorrow, particularly on a Warriors team that is suddenly starved for perimeter defense, most GMs would probably take Iguodala over Russell. 

So this is a long-term play, yes? Perhaps. If all goes according to plan, Russell thrives in Golden State's offense and becomes a young, budding-star building block that they would've had no other realistic means of acquiring. If that happens, the slot hit triple sevens. If he's good enough to maintain or even increase his trade value, and the Warriors get a package that puts them closer to championship contention in the short term, that's a win, too. 

The worst-case scenario is the Warriors, in the haste of losing Durant, jumped the gun giving a max deal to a one-time All-Star ... in the East ... who simply isn't worth what they paid. Russell can't play defense. His offense in Brooklyn was inflated and his shooting falls back to the 40 percent range, which in turn deflates his trade value and long story short, the Warriors are stuck for the next four years with a wildly overpaid player they can't trade without cutting their ear off. 

The answer, very likely, could be somewhere in the middle. Russell isn't an All-Star in the West but he's a good player; he did average 21 points and seven assists last season, and he went for 40-plus three times. Let's not get it twisted. He can really play. But let's say the season he had last year was somewhat circumstantial and he's not quite that good, and he's a weird fit, and while he might not ultimately command a huge trade package, the Warriors could trade for a pretty decent package for Russell given his age and upside. 

And something is better than nothing, which is what they would've had with Durant leaving as a free agent. This was really Golden State's one chance to land a young superstar to move forward with in the post-Curry/Thompson prime years. They had no money or trade assets to do it any other way, and Brooklyn was the only team they could deal with because that's where Durant was going on his own otherwise. 

It's not horrible. Given the team-friendly extension they just inked with Draymond Green, and the $17 million trade exception they got for Iguodala. this isn't going to kill the Warriors either way. But again, if the season Russell had last year turns out to be more an exception than the rule moving forward, there are surely ways that this deal, which seemed like free money at first glance, can backfire. 

Bucks let Malcolm Brogdon walk

If Giannis Antetokounmpo wasn't a free agent in the summer of 2021, trading Malcolm Brogdon to the Pacers -- for three future picks -- rather than paying him the $85 million over four years Indiana gave him, wouldn't seem like all that risky a move. You could argue, in fact, it would've been a shrewd move under normal conditions. Brogdon is not an All-Star. He's simply a good player, and over $20 million a year is steep for a Milwaukee team that just inked Khris Middleton to a five-year, $178 million deal. 

Fact is, that Middleton deal is probably an overpay, too -- but it's circumstantial, a lot like Tobias Harris getting $180 million in Philly -- more about a team right on the cusp not taking a step back than necessarily taking a step forward. Through that lens, there's really no way to argue the Bucks didn't take a step back by moving Brogdon. And for what? Maybe 5 or 10 million bucks in salary? Would they have been comfortable paying Brogdon the $70 million they gave Bledsoe?

There are tax considerations (Milwaukee is just under the luxury tax line as it is, and would've gone over for Brogdon), and these are steep penalties for a small-market team (ask OKC what it's like paying hundreds and hundreds of millions for a non-championship team). 

But again, this is about more that what the Bucks are now. They're paying now for the hope, the privilege, to eventually pay Giannis, who in 2021, given his combination of age and production, will be the hottest free agent on the market since LeBron James in 2010. The Bucks can offer Giannis the most money, just shy of $250 million over five years, but as we've seen for a lot of these young stars, money isn't everything. They're going to be silly rich no matter what. They want to win. 

The Bucks have one mission between now and then -- an even greater mission, perhaps, than actually winning a title (though the two might go hand in hand): Convince Giannis to deny the swarming pack of suitors and stay in Milwaukee. If that meant overpaying Brogdon a little bit, so be it, because there's really no alternative for the Bucks to replace him. They don't have the cap room to go get anyone even close to his caliber without trading existing parts. This was a pure money play. Perhaps prudent in one sense. Playing with fire in another. 

Eric Bledsoe is a huge X-factor here. A big reason -- if not the whole reason -- the Bucks cheaped out on Brogdon is because they inked Bledsoe to a four-year, $70 million deal last March. If he plays up to that consistently, including and most specifically in the playoffs, where he has been anything but consistent in the past, then Brogdon's loss won't be felt in nearly the same way.

But right now, it feels mighty risky if the Bucks fails to capitalize on this open championship window and end up losing Giannis in part because they were willing to lose Brogdon. 

Houston Rockets Introduce Russell Westbrook - Portraits
The Rockets took a huge risk this summer by investing serious money in Russell Westbrook. Getty Images

Rockets invest heavily in Russell Westbrook

Let's stay with the Bucks letting Brogdon walk for a second. On a smaller scale, this is what the Rockets did with Trevor Ariza last summer. They had a conference finals team in 2018, right on the brink of a championship, then let Ariza walk in the summer to the Suns, who only gave him a one-year deal for $15 million. Ariza wasn't the best player for the Rockets. Not even close. He's not as good as Brogdon was, or is, in fact. But he was central to Houston's ability to defend Golden State with his size and ability to switch everything defensively, and slotted perfectly as a floor-spacing shooter as James Harden and Chris Paul did their isolation work. 

Houston took a step back when it lost Ariza and went from a championship contender to a team kind of scrambling all season that eventually felt short to the Warriors even without Kevin Durant. Would Ariza have changed that? I'm certainly not going to say that. But this is a thought exercise. They cheaped out on Ariza, and now, perhaps in a bit of a get-back panic move as an impulsive response to seeing their title window close, they're pushing all their chips in on Russell Westbrook, who they now owe an obscene amount of money over the next four years. 

  • 2019: $38.5 million
  • 2020: $41.3 million
  • 2021: $44.2 million
  • 2022: $47 million

Seriously, look at those numbers for a guy who is, at best, a strange fit next to Harden and a really bad 3-point shooter in a system that almost completely relies on 3-pointers -- or at least the threat of them as Harden attacks the rim. Westbrook is going to put up good-to-great numbers and it was definitely a splash move to potentially re-energize a fading team, but were they really fading all that bad? Obviously Harden wanted Paul out of there, and Paul didn't seem to eager to stick around either, but the only team that was standing between the Rockets and a championship was the Warriors, and they came back to the pack and then some by losing Durant. 

This is the definition of risky, and it could get a lot worse as the contract goes on. It's hard to imagine the value on Westbrook not diminishing every year of this deal. By the time Houston is potentially paying him $47 million three years from now, when he's 34 years old, well, let's just say the Rockets are hoping the bet will have paid off by then. Serious gamble. 

Blazers take the three out of their D

Let's take a steep walk down the name-power ladder until we end up at ... Moe Harkless. The Blazers were part of the four-team deal that sent Jimmy Butler to Miami, and it cost them Harkless to the Heat, who re-routed him to the Clippers. Who did Portland get in return? Hassan Whiteside

In a perfect world, Whiteside can summon some of the player he was when he earned that $98 million deal from the Heat in 2016, though he was probably never actually worth that even at his best. But he is a monster rebounder and can protect the rim, which helps Portland on paper with Jusuf Nurkic still out for a good while with no guarantee he'll return to the player he was prior to his gruesome broken leg late last season, at least not in the short term. Look at how long it's taken Gordon Hayward

So Whiteside can help, maybe, but don't necessarily count on it. What you can count on is the Blazers, as currently constructed, having a major hole at small forward. On paper, they have Rodney Hood and Nassir Little, who has never played a single NBA minute. But in a conference that boasts LeBron James, Kawhi Leonard and Paul George, defending the three/stretch-four position with a like-sized, at least halfway capable athlete like Harkless seems like a bare minimum for any team with conference title aspirations, which the Blazers certainly have. 

Portland fans will gripe about Aminu's shooting, but he is a born defender with unteachable size and length and instincts. The Blazers, who have been in salary cap hell for ill-advised 2016 decisions for years, can explain not ponying up for Aminu. But Harkless is on an expiring deal. To not play that out for one more year of a premium-position defender is, well, risky. They didn't have to bring in Whiteside, which was in part a necessity because they let Enes Kanter walk, which, again, they didn't have to do. 

None of these guys are real difference-makers on their own. Harkless, Whiteside and Kanter are all flawed, in some cases seriously flawed. But on a team with Damian Lillard and CJ McCollum, you're just trying to plug the right holes. instead, by letting Harkless walk, they appear to have opened up a big one. Maybe Portland will be active at the trade deadline, or maybe Little will bust out as a rookie and contribute defensively right away (a scout I've spoken with says he has top-10 or in some cases even top-five talent). 

But those are unknowns. For now, Blazers fans are thinking about a second-round matchup with the Lakers or Clippers and having to watch Rodney Hood play 40 minutes defending LeBron, Kawhi and/or George, maybe with a little help from ... Zach Collins. It's not pretty on paper.