fb-pixelDamian Lillard trade: How the Bucks' big move affects the Celtics Skip to main content
Gary Washburn | On basketball

With Damian Lillard traded to the Bucks, the Celtics’ road to a championship got a bit tougher

Damian Lillard averaged a career-high 32.2 points per game for the Trail Blazers last season.Kevin Kolczynski/Associated Press

There had been so many superimposed photos of Damian Lillard in a Miami Heat jersey it seemed as if he had already purchased a condo on South Beach in preparation of playing there.

He wanted to go to Miami. He wanted to leave Portland and its rebuilding plan. Instead, Trail Blazers general manager Joe Cronin worked out a deal with another Eastern Conference contender in a three-team blockbuster trade.

Lillard will be paired with two-time MVP Giannis Antetokounmpo with the Milwaukee Bucks, as the club pushed all of its chips in the middle of the proverbial NBA Finals title by moving stellar two-way guard Jrue Holiday to the Trail Blazers and key reserve Grayson Allen to the Phoenix Suns.

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The Celtics remain the favorites in the Eastern Conference, although the Bucks will be more offensively entertaining and more difficult to contain because of Lillard’s ability to score in bunches. But they are now older. Lillard is 33 and has dealt with numerous injuries the past few years and the supporting cast for Antetokounmpo is also aging.

The Bucks are going all-in on winning a title now by adding a 33-year-old superstar in Damian Lillard.Steve Dykes/Associated Press

Brook Lopez is 35. Khris Middleton is 32 and shot just 31.5 percent from the 3-point line in an injury-marred 2022-23 season. Former Celtic Jae Crowder is 33. The aging Bucks will play under a new coach in Adrian Griffin in his first NBA job.

The betting sites immediately boosted the Bucks to the top of the NBA championship odds. And yes, they became more dynamic, but losing Holiday could be a blow. He’s one of the league’s best defensive guards. He can score, shooting nearly 40 percent from the 3-point line in his three years in Milwaukee.

Allen, as maligned as he has been during his career for his overly physical and questionable play, was a key contributor off the bench and a career 40 percent 3-point shooter. It’s uncertain what style of play Griffin will implement , but it won’t be difficult to pair Lillard and Antetokounmpo in pick-and-rolls.

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But defense could be an issue. Holiday was assigned to the opposing team’s best scorer, giving the Bucks an edge. Who in the world is going to guard Jayson Tatum? Or even Jaylen Brown?

Another wrinkle in this trade is the future of Holiday. The Trail Blazers are going young and a 32-year-old point guard won’t fit when they just drafted Scoot Henderson to be their floor leader of the future. The Blazers are likely to want expiring contracts, prospects and draft picks for Holiday, who has an expiring contract of $36 million and a player option for 2024-25 at $39 million.

Now, the Celtics could package Malcolm Brogdon, Al Horford, and multiple first-round picks for the rights to Holiday, who would assume point-guard duties and send Derrick White back to his shooting guard position. It all depends on the Trail Blazers.

Portland is certainly going to get multiple offers for Holiday, a group of teams that likely include Miami and Philadelphia. Holiday is a game-changing player who remains in his prime and with something to prove after being suddenly dislodged from a Finals contender to a lottery team.

Celtics president of basketball operations Brad Stevens might not mess with the roster but he nearly traded Brogdon to the Clippers in July and may be intrigued by the possibility of acquiring a two-time All-Star point guard and three-time All-Defensive team selection to a team with two All-Stars primed for a deep playoff run.

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Jrue Holiday is now on the Trail Blazers, but the veteran point guard could be a smart target for NBA title contenders like the Celtics.Morry Gash/Associated Press

It’s definitely something for Stevens to think about. But again, it all depends on Cronin, who waited all summer to make the more profitable deal for Lillard, who demanded a trade to the Heat before relenting and including other clubs when talks with Miami stalled.

Holiday’s value could be increased at the trade deadline, but it appears Cronin will receive enough lucrative offers filled with future first-round picks and assets to make a deal soon. Stevens told the Globe on Tuesday he was content with the current roster, especially with the summer additions of Lamar Stevens, Kristaps Porzingis, and Oshae Brissett.

But he is likely inclined to make a call to Cronin to figure out an asking price. Holiday would make the Celtics a championship favorite again and complete the league’s best starting lineup.

As of now, the Celtics are still the best team in the Eastern Conference, and Blazers sending Lillard to the Bucks damages the Heat’s contending chances. They saved roster space for a potential Lillard deal and just hours after the deal was announced, Miami made a series of minor roster moves as it attempts to make amends with Tyler Herro, who was dangled for months for Lillard.

While the Bucks made headlines Wednesday and brought in a bona fide superstar, the price may have been too high unless their aging core can respond with standout seasons. The Celtics have two players 30 and over — Brogdon and Horford. The rest of the core is in its prime or nearing that point. That’s what makes them the championship favorites.

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Although the competition may have gotten tougher with one of the league’s best players heading east.


Gary Washburn is a Globe columnist. He can be reached at gary.washburn@globe.com. Follow him @GwashburnGlobe.