Basketball Poetry

Basketball Poetry

The 7 riskiest moves of the offseason

Kawhi Leonard, Trae Young, guaranteed money for slot-machine centers, and much more

Mike Shearer
Aug 11, 2026
∙ Paid

Every transaction in the NBA is a gamble.

Lead executives are gambling that their talent evaluations are correct. They’re gambling that they know what their competitors will do. They’re gambling on player health, physical and mental. They’re gambling on chemistry forming, on personalities meshing.

But not all transactions have the same odds. Some are clear winners, while others are a bit murkier. I wanted to examine some of the higher-leverage moves that could swing the fortunes of several franchises, the riskiest bets placed.

Note that “risky” doesn’t always mean I disapprove (although I certainly do not like many of the moves below, as you’ll notice). You have to take a swing to hit a home run, after all. Risky, for these purposes, means a wide range of outcomes.

So, for example, I don’t view the Bucks’ $64 million deal for Gary Trent as risky. What, are the Bucks scared the league might take a first-round pick away from them? That’s what it would take to get off this contract anyway! (And with Damian Lillard’s stretched dead money on the books for the next few years, the finances were already kinda ruined.)

Let’s dig in.

Trae Young’s contract

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