When Damian Lillard requested a trade not just from the Portland Trail Blazers, but specifically to the Miami Heat, he put the organization with which he has spent his entire career in a heck of a tough spot. Give general manager Joe Cronin credit. He didn't buckle under the pressure and take Miami's cut-rate offer because, as many folks ridiculously believed, he owed it to Lillard to send him to the destination of his preference.
The Portland Trail Blazers didn't owe Damian Lillard a thing. Frankly, they could've not traded him at all. He still has four years left on his contract. But if they were going to trade him, they owed it to their organization and the fans that pay all their salaries, including Lillard's, to do what was best for the Portland Trail Blazers.
The deal they got from the Milwaukee Bucks was the best deal out there. As a bonus, it's also a great deal for Lillard, who gets to join a ready-made title contender for a run at his first ring. Everyone wins.
Except, of course, the Heat, who banked on Lillard's sway over the Blazers being enough currency to get him despite not having the most attractive trade package.
Instead of Tyler Herro, the Blazers bring in Jrue Holiday, who will surely be flipped for at least one -- and I would argue probably two -- future first-round picks. Instead of Miami's two future picks that will probably be in late teens or 20s with they materialize, the Blazers basically land what could be three picks from the Bucks in the form of a guaranteed first-rounder in 2029 and swap rights in 2028 and 2030.
That's five to seven years from now. Do the math. In July of 2028, Lillard will be 38 years old. In August of that year, Khris Middleton, in the unlikely event that he is still with the Bucks, will be 37. Lillard's arrival is enough to satisfy a 28-year-old Giannis Antetokounmpo right now, but this is very likely a short-term play in Milwaukee, which, with no drat capital left and Lillard's behemoth salary set to hit the books, has zero flexibility to build out a roster that can contend for titles beyond this era.
In other words, when this ends, the Bucks are a good bet to be pretty bad. And when that happens, the Blazers will be sitting on potentially three of their draft picks. It's not unreasonable at all that one or even more than one of those picks ends up in the top five. Maybe even No. 1 overall.
Meanwhile, the Blazers also, finally, cut ties with Jusuf Nurkic, and in doing so get Deandre Ayton, who is still just 25 years old. Maybe he takes to the change of scenery, gets a bigger opportunity with Portland, and turns himself into another potential trade candidate for another first-round pick. Or maybe he's just good. And he sticks as a big-man anchor on a guard-heavy team. Jerami Grant could still be traded for potentially more first-round picks. Perhaps Anfernee Simons as well.
With Scoot Henderson and Shaedon Sharpe and all of this incoming capital, both potential and real, the Blazers came out of this smelling like a rose garden. (Sorry, I had to do it.) Had Cronin conceded to Dame and shipped him to Miami, it would've earned him some temporary street credit, I suppose, with other superstars who will likely never play for Portland anyway and their agents, but after the dust settled he would've come out looking like a sucker.
Instead, he held firm. He got the best deal he could get for the team he is responsible for, and he still did right by Lillard by sending him to a contender. If that's not winning, I don't know what is.