Winners, losers from blockbuster Damian Lillard trade to Milwaukee

The NBA is the master of misdirection. Look over here, talk about Toronto and Miami as destinations for Damian Lillard to chase a ring.

Boom — in sweeps Milwaukee with a blockbuster trade, sending out Jrue Holiday in a deal that lands them a 75th Anniversary Team player in Lillard to go next to the two-time MVP one they already had in Giannis Antetokounmpo. The Trail Blazers get what they want, and the Suns get some depth (but do they get better?).

Let's break the winners and losers of this trade down, but first, the trade breaks down this way:
Milwaukee receives: Damian Lillard
Portland receives: Jrue Holiday, Deandre Ayton, Toumani Camara, Bucks 2029 first-round pick, and two pick swaps from the Bucks
Phoenix receives: Jusuf Nurkic, Nassir Little, Keyon Johnson, Grayson Allen

Winner: Giannis Antetokounmpo

Antetokounmpo threw down the gauntlet and challenged the Milwaukee Bucks with the threat of him leaving after this contract in two years.

"I'm a Milwaukee Buck, but most importantly I'm a winner… If there is a better situation for me to win the Larry O'Brien I have to take that better situation," Antetokounmpo said this summer.

The Trail Blazers heard him and went all-in trading for Lillard — someone Antetokounmpo has had a public mutual admiration society with. Antetokounmpo got what he wanted, the Bucks are better and serious title contenders for the next two years. Then next summer, the Bucks will put the largest contract in NBA history in front of him to sign. Unless he never intended to stay, Antetokounmpo got what he wanted. He won.

Winner: Milwaukee Bucks

Jrue Holiday is an outstanding player, an All-Star, a strong floor general and an elite perimeter defender — he's a key reason the Bucks hung a championship banner a couple of years ago.

Damian Lillard is better. Full stop. Lillard is one of the elite offensive weapons in the game, a clutch player who can carry a franchise. He's the kind of guy that ends up on the bottom half of MVP ballots. He makes the Bucks more dangerous, and most importantly for that title run, he gives them another shot creator in the half-court in the playoffs (a job that used to fall to Khris Middleton). The Bucks now have Middleton as their third option — their offense will be a juggernaut. This team is the new betting favorite to win the title for a reason.

Lillard for Holiday isn't even the biggest reason the Bucks are winners here — it's about Antetokounmpo signing an extension next summer.

Here is Antetokounmpo's quote this offseason about signing an extension next summer: "I would not be the best version of myself if I don't know that everybody's on the same page, everybody's going for a championship, everybody's going to sacrifice time away from their family like I do. And if I don't feel that, I'm not signing." Well, is trading for Lillard enough of a commitment for you? If not, he never had any intention of staying anyway. This feels very similar to 2020 when other teams thought the Greek Freak might bolt Milwaukee, then the Bucks signed Holiday and Antetokounmpo opted to stay. And won a ring. (There are some around the league who thought he was as good as gone this time, we'll see how this changes the vibe.)

Loser: Miami Heat

This was a punch to the gut, even if Heat fans may have seen it coming in the last week and can justify not making their biggest, best offer. Miami needs a point guard after Gabe Vincent went to the Left Coast, Lillard demanded to go there, and he was a perfect fit — exactly the guy the Heat needed to help generate offense in the playoffs. Pat Riley and the Heat front office didn't even play this wrong (Portland seemed frustrated with Lillard's agent and apparently due to that didn't want to send the superstar to his preferred, sunny destination). Things just did not break Miami's way.

Without Vincent and Max Strus (now a Cavalier), Miami is worse than they were a year ago. There could be a good consolation prize if Miami can talk to Portland and swing a Jrue Holiday trade, but the big fish got away. That doesn't happen often to Pat Riley.

Winner: Damian Lillard

Milwaukee may not be the destination he wanted, it's a little bit colder there in February than South Beach, but this was a win of a landing spot for a guy who wants a ring to complete his legacy.

Nobody should blame Lillard for asking out of Portland. He wanted to win, the Trail Blazers made it clear with their actions that they wanted to rebuild — this is a no-fault divorce. What was best for both sides was to part ways. Lillard lands on a team with Antetokounmpo that is a clear title favorite, which appears to be an acceptable outcome for him. It should be.

Now the pressure is on him to live up to that legacy.

TBD: Portland Trail Blazers (but mostly a win)

This feels like a win for the Trail Blazers, but we're not fully endorsing that call until we see what Portland can flip Jrue Holiday for.

From the start Portland wanted nothing to do with Miami's offer — Tyler Herro, a couple of picks, filler and maybe a young player or two — and as the Blazers ignored the Heat in recent weeks it felt like that was a mandate from somewhere in the organization (maybe due to frustration with Lillard's agent and how he approached the trade request). It worked for Portland, which ended up with something likely better than the Heat offer, and they got it done before the start of training camp, avoiding that distraction.

Ayton is a better center than Nurkic and at age 25 is closer to the timeline of their young stars. They get a first-round pick, a couple of pick swaps, plus whatever they get in another Holiday trade. More importantly, they have cleared the runway for a team built around a young Scoot Henderson, with Shaedon Sharpe and Anfernee Simons. And now Ayton, too.

Winner: Deandre Ayton

Part of Ayton's clashes with former Suns coach Monty Williams and the entire Phoenix organization was about his role. Ayton wanted more touches, more post-ups, and a bigger part in the offense. Frank Vogel may now be the coach but he's not an idiot — with Kevin Durant, Devin Booker and Bradley Beal on the team, Ayton's offensive role would get smaller.

Ayton is now one of the cornerstones of a rebuild in Portland, he will get the bigger role and the touches he wanted. Now we'll see what he can do with them.

TBD: Jrue Holiday

This week, Holiday said to a reporter, "[I] would love to [sign an extension with Milwaukee]. Before I even won here I think I said I'm a Buck for life and I mean that like deep in my heart." Well, so much for that.

In the sense of surprisingly getting traded, it would be easy to call Holiday a loser here, but it kind of depends on where he is traded. He could end up with the Clippers and be back home in Los Angeles, where he grew up and went to college (UCLA). He could end up on a contender in Miami with Jimmy Butler and Bam Adebayo. Until we see where Holiday lands, this is TBD. Still, it's fair to say this is not ideal for him.

Winner: NBA Fans

No more Damian Lillard trade updates! Halelujuia!

Now, if they can just settle the James Harden situation….