2025 NBA Free Agent Signings That Hurt

The NBA has entered Day 2 of Free Agency, 2025. Players are getting scooped up like crazy. The shocking news of the day has been the Milwaukee Bucks waiving Damian Lillard in a historically big contract stretch. Close on the heels of that is Indiana Pacers center Myles Turner defecting to the Bucks, presumably the reason Milwaukee made a move that will add $22 million of dead money to their cap for the next five years.

The Portland Trail Blazers haven’t made any moves early in free agency save waiving center Deandre Ayton. Trading Anfernee Simons for Jrue Holiday last week was their big splash. We’ll see if they try to acquire anyone as the action continues to unfold.

That said, every year at least one or two free agency signings make you say, “What if?” They’re the kind that hurt your heart, because you halfway wish your own team got those players instead, especially given the amount of money involved.

So far this year I’ve seen two for Portland.

One will come as no surprise to anyone who read our pre-free-agency Mailbag. Ty Jerome is reportedly signing with the Memphis Grizzlies for a three-year, $28 million contract. Jerome has a player option in Year 3, but that’s still at least two solid years of service from the bench guard for a little more than $9 million per season. Or, put another way, Jerome’s whole contract was about one year of Simons pay. That’s a pretty good deal.

The other one was point guard Tyus Jones going to the Orlando Magic for a one-year, $7 million deal. Jones is a little short at 6’1 and his defense isn’t great, but he is a good distributor, a heady point guard, and he shot 41.4% from the three-point arc last season on 5.0 attempts per game. He would become the third point guard on the squad for now, but I’m not a huge believer that Jrue Holiday and Scoot Henderson will co-exist in the same lineup forever. Jones would be relief for either, either extending Holiday’s distributive play or providing a nice contrast to Scoot when a more traditional point guard was called for.

Neither Jones nor Jerome would revolutionize the team on their own, but I love them individually and together as awesome back-ups at the guard spots. They’re the kind of players that would round out a playoffs team in fine form. The Blazers may not be a playoffs team yet, but they seem to be angling that way. Getting either player on an inexpensive contract would have been a nice bonus in free agency.

These signings, and a dozen or so others, underline something about the new CBA. Stars like Shai Gilgeous-Alexander—who just signed the richest contract in league history—are going to prosper under this system. Middle-ground salaries appear to be down, or at least contained, even though the cap itself is rising. You’re not seeing a lot of $15-20 million per year signings nowadays, or even full MLE’s being used on single players. Above $30 million and below $10 million seem to be the order of the day. Maybe that’s an artifact of this particular free agent class, but it feels like the league is headed towards a “have” and “have not” system where we get closer and closer to stars demanding (and getting) near-max deals while players without as much leverage get pushed closer towards the minimum.

Either way, seeing a potentially-excellent pair of guards sign for about the amount of a Mid-Level Exception combined is certainly interesting. Good players out there are going for great prices. Let’s see if, and when, Portland gets in the game.

Have any signings hurt for you so far? Share them in the comments section below.