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Damian Lillard to play with Giannis Antetokounmpo and Bucks?

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James Foglio
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James Foglio Sports Editor

James is a Basketball Insiders contributor. He earned his bachelor's degree in English and Creative Writing from Southern New Hampshire University. James enjoys watching sports and helping gamblers win money.

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Sports Editor

Updated27 Apr 2023

Trail Blazers Damian Lillard to play with Giannis Antetokounmpo and Bucks?

Damian Lillard of the Portland Trail Blazers retweeted an image of himself and Giannis Antetokounmpo in Portland jerseys, but the more ideal scenario is Lillard asking for a trade to Milwaukee. The six-time All-NBA member inked a two-year, $121.77 million max veteran extension with the Trail Blazers last July.

Lillard made $42,492,492 this season and is projected to earn $45,640,084 in 2023-24. More importantly, the guard exercised his $48,787,676 player option with Portland for 2024-25 last offseason as well. If a deal manifests in the months ahead between the two teams, the guard cannot be traded until July 9 due to contract restrictions.

Referring to a few NBA betting sites, the Trail Blazers have a 10.5% chance of receiving the No. 1 overall pick in the 2023 NBA Draft Lottery. Sportsbooks show the San Antonio Spurs, Houston Rockets, and Detroit Pistons with a 14% probability of winning the first overall pick.

Since Giannis Antetokounmpo wants to win, it would make little sense for Milwaukee to trade its 10-year veteran to Portland. Therefore, if Damian Lillard wants to play alongside the two-time MVP, he would have to join him on the Bucks. Antetokounmpo signed a five-year, $228 million max veteran extension with Milwaukee in 2020.

With the Bucks, the seven-time All-Star earned $42,492,492 this season and is set to make $45,640,084 next season. The Greek Freak also has a 2025-26 player option worth $51,935,268. So, he’s locked in for the foreseeable future.

Would Trail Blazers star Damian Lillard be up to playing with Giannis Antetokounmpo on the Bucks?

The Trail Blazers or Bucks trading away their superstar will be a tall order. What general manager would want to move on from a player who just averaged a career-high 32.2 points per game in only 58 starts? Lillard dealt with an abdominal injury in the 2021-22 season, but he’s still one of the best players in the league today.

Likewise, Antetokounmpo averaged a career-high 31.1 points in 63 starts this past regular season. For one downside of such a trade, the Bucks would probably have to tear their team apart to acquire Damian Lillard. That’s not practical for a championship contender.

Bucks G.M. Jon Horst might have to package Jrue Holiday and/or Pat Connaughton, along with at least a second-round draft pick for the Trail Blazers star. This is not ideal for a team that finished with an Eastern Conference-best record of 58-24.

Even then, Portland G.M. Joe Cronin could put his foot down and demand at least one first-rounder. At the age of 32, Lillard just played the best season offensively of his 11-year career. If the Bucks had to give up Holiday, a first-rounder, and Connaughton for Damian Lillard, that might not sit well with some Milwaukee fans. The price will be high.

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