The 7 riskiest moves of the offseason

Big trades, little player options, horrible timing, and more

We’re still waiting to hear what happens with Cam Thomas, Quentin Grimes, Josh Giddey, and Jonathan Kuminga, but other than that, the offseason is mostly settled.

In lieu of a traditional best/worst moves column, I wanted to explore instead some of the riskier moves that teams made. Risky does not inherently mean bad, and I’m very excited about some of the transactions we’ll talk about below, but it does mean that there is real potential downside.

1) The Suns extend Booker early

I get that Booker is a bastion of Suns culture (for whatever that’s worth). He’s loved locally, and he’s been an outstanding NBA player for a long time.

But giving super-maximum money (~35% of the salary cap!) to a guy who didn’t make an All-Star team last year is foolish. To do so two years before needed is even worse!

Booker will be 32 and 33 in the years he’s making nearly $70 million (2028-29 and 2029-30 seasons). Why are the Suns in such a rush to lock him up for the most they could possibly pay him?

It’s unfathomably poor roster management that’s turned Devin Booker, star player, into Devin Booker, terrible contract. His humanity is lost now, transmogrified into discourse that leans too heavily into phrases like “toxic asset” and “underwater” and “why, God, why?”

There are so many ways for this to go badly and so few in which it goes well.

But hey, good for Booker! Get your money, young man.

2) The Knicks change coaches

I was in favor of the Knicks replacing Thibodeau, even if he addressed some of my concerns with his postseason coaching. A new voice (and more importantly, a new offensive system) was needed.

That said, I felt better about the move when I assumed the Knicks had a successor in mind. It turns out that they misplayed the Jason Kidd situation in Dallas, and then had to go courting a half-dozen other coaches before they finally settled on their man, Mike Brown.

I’ve generally been a fan of Brown, and he was last seen using a Golden State Warriors-style movement offense in Sacramento. That system could not be more different from the Brunson-centric attack New York has run over the last few seasons. Expect to see more of Karl-Anthony Towns as a high-post hub, mimicking Draymond Green and Domantas Sabonis. It’ll be fun to watch Towns as a decision-maker. KAT is a tremendously gifted and staunchly goofy passer, sometimes at the same time:

His ability to lean more former than latter could determine New York’s ceiling.

Both Brown and the players will need to adjust significantly to replicate last year’s team success. Making it to the conference finals is hard; it’s entirely possible that Brown comes in, does a great job, and the team still doesn’t advance as far.

For all of Thibodeau’s woes, you knew exactly what you were going to get from him (so did opponents; that was part of the problem). It’s always a risk to shake up a successful team. Brown isn’t an unknown quantity by any means, but he represents major change for a team that is banking on the benefits of roster continuity. It was a necessary move, but that doesn’t mean it won’t backfire.

3) The Magic go all-in on Bane

I wrote in-depth about this trade at the time, and my feelings haven’t changed much. I love the Desmond Bane/Paolo Banchero/Franz Wagner/Jalen Suggs quartet on paper. But the Magic are essentially locked into this core going forward. They have few draft picks left to trade after sending out four firsts for Bane.

Would I have made this move? Yes. But adding Bane only works if Banchero and Wagner are on true #1 and #2 growth trajectories. At least one will have to become a more dangerous shooter, and both will need to improve their off-ball movement. Banchero and Wagner are really good players. They’ll need to become great.

They’re certainly being paid like great players. This roster has limited financial flexibility post-trade. Bane, Banchero, Wagner, and Suggs combined will make up about 90% of the salary cap alone in 2026-27. If they don’t coalesce the way the Magic think they will, Orlando will need to jettison some of those big contracts eventually.

I’m very excited for Orlando this season, particularly in a weakened East, but I’d be lying if I said I wasn’t nervous for their future.

4) You get a player option! You get a player option!

You may have assumed I’d have the Damian Lillard waive-and-stretch here, but I don’t view that as a risk since it’s become actualized: the Milwaukee Bucks no longer employ Lillard, portioning him into five $22.5 million payments each year going forward. It’s an operational certainty now. The upsides (lower tax bill, more financial flexibility to bring in a guy like Myles Turner during Giannis’ waning prime) and downsides (starting with a handicap every year) are realized.

The Lillard/Turner situation dominated Bucks headlines, but they actually had a rather nice summer other than that, re-signing key free agents and bringing in some buy-low veterans like Cole Anthony and Gary Harris.

But they also signed or re-signed five players (Kevin Porter Jr., Gary Trent Jr., Gary Harris, Taurean Prince, Jericho Sims) to 1+1 deals, meaning they have a player option in 2026-27. (They also gave Ryan Rollins and Bobby Portis 2+1 contracts, giving them control of their fate in 2027-28.) All those player options significantly hamper their flexibility next season (although the Bucks did well to get most of their signees to waive their implicit no-trade clause).

To have so many players in control of a roster spot next year just makes future planning harder. If it turns out some of these guys aren’t NBA-caliber anymore? Too bad, Milwaukee will be stuck with them. If they play fantastically and earn themselves a bigger payday? They’ll hit the market in a summer where plenty of teams will have at least a bit of salary cap room.

(In recent years, player options have surprisingly become a useful tool for teams when the option is tacked onto the end of bigger deals for older players; teams have been able to convince guys to opt out of that final year and re-sign for longer, lower AAV contracts. But Bobby Portis is the only player where that might remotely apply here.)

None of these are major risks in and of themselves, given the low contract value for most of these players. Giving out player options is sometimes the cost of doing business, the carrot that convinces players to sign for a bit less than they might think they’re worth. But the cumulative effects of five different player options for next season add up to something the Bucks will need to worry about.

5) The Pelicans dig themselves deeper

Everything went downhill when the Pelicans hired Joe Dumars (who’d been out of a teambuilding role for more than a decade) and Troy Weaver to head the front office, for, uh, reasons?

Maybe that’s not fair. New Orleans wasn’t exactly flying high to begin with; they were already at the bottom of said hill. There was no more hill to go down. They went subterranean.