Winners and losers of the Damian Lillard trade

PORTLAND, OREGON - APRIL 02: Giannis Antetokounmpo #34 of the Milwaukee Bucks dribbles against Damian Lillard #0 of the Portland Trail Blazers in the third quarter at Moda Center on April 02, 2021 in Portland, Oregon. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Abbie Parr/Getty Images)
PORTLAND, OREGON - APRIL 02: Giannis Antetokounmpo #34 of the Milwaukee Bucks dribbles against Damian Lillard #0 of the Portland Trail Blazers in the third quarter at Moda Center on April 02, 2021 in Portland, Oregon. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Abbie Parr/Getty Images) /

Damian Lillard has been traded, but not to the Miami Heat. Instead in a surprise move, the Milwaukee Bucks acquired Lillard from the Portland Trail Blazers in a three-team deal that included the Phoenix Suns. Let’s get to the biggest winners and losers of the trade.

Winner: The Milwaukee Bucks

Lillard will join Giannis Antetokounmpo to form the most devastating two-man game in the NBA. The two are a hand-in-glove fit much in the same way Lillard would have seamlessly fit with Bam Adebayo and Jimmy Butler, only in this version it’s with a two-time MVP and perhaps the best player in all the league.

No player puts more pressure on the rim than Giannis, and no player outside of the Bay Area spaces the floor as much as Lillard. Defenses won’t know which way to go. Put bodies in the paint to defend against Antetokounmpo’s surges to the basket, or have your defenders prepared to pick up Lillard at 30 feet? It’s an impossible decision for any opposing coach.

If there is a critique to the deal, which sent away Jrue Holiday, Grayson Allen, an unprotected 2029 first-round pick and swaps in 2028 and 2030, it’s that it leaves the Bucks with questions on defense. A projected starting lineup of Lillard, Giannis, a rapidly aging Khris Middleton, Brook Lopez and either Malik Beasley or Pat Connaughton is certainly shaky on that end. But Giannis, perhaps the NBA’s most disruptive defender, covers up for a lot of weaknesses, and last I checked Lopez is still seven feet tall. Lillard and Milwaukee’s other guards will have a hard time staying in front of elite ball handlers, but they’ll also have plenty of support behind them. There are depth concerns, but Bobby Portis is still around and maybe Jae Crowder can give them something this season or one of MarJon Beauchamp or Andre Jackson Jr. pops.

The Bucks should be considered the clear favorites in the East and on the same tier as the Denver Nuggets and Phoenix Suns as top-end championship contenders.

But the real reason the Bucks are winners is because of what this could mean for Giannis, who put the organization on notice when he told the New York Times that he wanted to see the team make moves before signing an extension next summer. Well, this is one heck of a way for the Bucks to show Giannis they’re committed to winning championships.

Loser: The Miami Heat

This is a tough blow for the Heat, who reportedly were not “desperate” to add Lillard but had also held off on other offseason business with the intent of trading for Lillard. According to reports, the Heat and Blazers did not talk after a brief conversation soon following Lillard’s trade request on July 1. The Blazers clearly did not want to deal with the Heat in this scenario.

Now the Heat go into training camp with a good roster, but one with the same offensive issues it had when they won 44 games last regular season. Before Jimmy Butler went full Super Saiyan and lifted the Heat to the Finals, Miami’s offense sputtered between the Tyler Herro-Bam Adebayo pick-and-roll and occasional Butler isolations. Butler doesn’t want to carry the offense in the regular season the way he does in the playoffs, and the Herro-Bam PnR yielded only average results.

Lillard would have given the Heat an identity. Coach Erik Spoelstra would have reoriented the offense around the Lillard-Bam Adebayo pick-and-roll, allowing Butler to thrive as an off-ball cutter and Adebayo as a rocking rim-finisher. Lillard has been among the league’s best pick-and-roll ball-handlers for years and, when that failed, is also an elite isolation scorer.

Spo will tinker and find solutions, but this team has won despite its mediocre offense. Adding Lillard would have been a needed jolt. Now, they’ll have to find that jolt from another source.

Winner: Small markets

If you think the NBA has a problem with stars leaving small markets for big markets like L.A., New York or Miami, well, then this trade is for you.

In the wake of the uproar over Lillard having one preferred destination, he ended up going from one small market (Portland) to another (Milwaukee). Yes, the second small market also happens to have one of the biggest NBA stars on the planet and legitimate championship aspirations, but it’s a small market nonetheless.

Loser: The Trail Blazers

After all the hemming and hawing over Lillard’s trade value, here’s what Portland got for him: Holiday, Deandre Ayton, Toumani Camara, one first-round pick, and two swaps.

The Blazers will try to spin Holiday into additional assets. ESPN’s Brian Windhorst reported that contending teams have already shown interest in the 33-year-old guard.

"“But because Holiday’s skill set — he’s a voracious defender coming off one of the best offensive seasons of his 14-year career — is so desired by contenders in the league. That he’s got championship experience and can play a variety of different roles only makes him more valuable on a star-laden team.”"

Holiday is on the books for $35 million this season and has a $37.3 million player option for next season. We’ll see what the Blazers end up getting for Holiday, which will ultimately determine how great a haul they got for Lillard.

On the flip side, it can be argued that the Heat’s reported offer of Tyler Herro and two first-round picks is a better starting point than what the Bucks gave up. If Portland showed any willingness to engage Miami’s front office, they might have been able to get the swaps and another young player like Jaime Jaquez Jr. or Nikola Jovic. But because Blazers GM Joe Cronin refused to do business with the Heat (and after allowing the media to lambaste Herro’s perceived trade value) he put himself in a position where he couldn’t accept Miami’s offer.

The Suns part of the deal would have always been there regardless of what team acquired Lillard. Adding Ayton, Herro, and two first-round picks (instead of one) — plus the swaps and whatever else Miami would have thrown in — is arguably a better return. But Portland will never know.

Loser: Jrue Holiday

Holiday goes from a core member of a championship team to a rebuilding outfit in Portland. It’s unlikely he stays there very long, and may never even suit up in the Blazers uniform, but his uncertain future must be unsettling.

According to ESPN’s Adrian Wojnarowski, the Blazers “remain engaged elsewhere on deals and will are expected to immediately engage contending teams on trade talks to move on Holiday.”

Teams like the Clippers, 76ers and Heat make sense as potential landing spots for Holiday. His contract is a near-match for James Harden’s and could be used to facilitate a multi-team deal and send Holiday to Philadelphia. The Clippers have expiring contracts and up to two future first-round picks.

Meanwhile, the Heat have an all-but stated need at point guard. But after Cronin refused to engage with them on a Lillard trade, would the Heat’s top brass really want to talk about Holiday? A potential offer could include Lowry’s expiring contract and a first-round pick.

Holiday’s fit in Miami makes sense on paper. Even at his age, he may still be the best defensive guard in the NBA, he has championship experience and was born just nine months after Butler. The problem is that he doesn’t solve Miami’s issues on offense. While he’s a good 3-point shooter (career 36.6%) he doesn’t strike fear in opponents like Lillard. He’s a good pick-and-roll ball-handler but most of his impact is derived from who he’s passing to (such as Giannis) than his own finishing ability. Like the Heat, the Bucks have had issues scoring in the halfcourt come playoff time. Holiday was part of the problem.

If I were the Heat, I’d hold onto my assets for the next star who asks for a trade or use them to acquire players who help solve my issues scoring or fill a long-term roster need. Those could be conversations for another day. Damian Lillard has joined a rival, the Eastern Conference landscape has dramatically shifted. It’s time to reevaluate.

Next. Should the Heat trade for James Harden?. dark