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Bucks' path to reacquiring discarded draft picks is staring them in the face

A trade with Milwaukee, Portland, and Boston has positves for every party.
Milwaukee Bucks forward Giannis Antetokounmpo (34) reacts after a play against the Orlando Magic in the first quarter at Kia Center on January 10, 2025.
Milwaukee Bucks forward Giannis Antetokounmpo (34) reacts after a play against the Orlando Magic in the first quarter at Kia Center on January 10, 2025. | Nathan Ray Seebeck-Imagn Images

The Milwaukee Bucks are short on draft capital at the moment, given that they sent a good chunk of it out in the 2023 Damian Lillard trade. With so much chatter about a Giannis Antetokounmpo trade, the Bucks getting their own picks back, whether directly through Portland or with the Trail Blazers as a facilitator, has been making the rounds.

While a Giannis to Portland trade seems unlikely, though not impossible, getting them involved one way or another feels like a logical move, and the Boston Celtics could oblige. Rip City Project's Reese Kunz proposed a massive three-team trade between all three parties that would shake up the NBA, headlined by sending former Finals MVPs to new squads.

Why the Bucks do it

There aren't many teams that can offer an adequate balance of draft capital and solid young players. Portland is one of those franchises. Even if they won't get Giannis, they could indirectly help replenish Milwaukee's draft and young player stash in a move like this, setting the Bucks up nicely for the next several years.

From the moment the Giannis rumors started floating around, the Bucks said they want a blue-chip prospect in an Antetokounmpo trade. They would get two here. Henderson was the third overall pick just a few short years ago, while Sharpe, also still young, has shown explosive upside when healthy. These two could give the Bucks a nice young duo to build with, in addition to their draft picks.

It's a better return than what teams like Minnesota or Golden State, which are either pick-heavy or player-heavy, can offer.

Why the Celtics do it

Stunning first-round exits can make teams do wild things. Remember when the Bucks suddenly went out and traded for Damian Lillard after their first-round exit? After being stunningly struck down by the Philadelphia 76ers, perhaps trading for Giannis could be Boston's version of the Lillard deal. The hope is that it would work out much better for them, though.

While Brown is an All-NBA caliber player, he's not Antetokounmpo. If Boston thinks it's time to break up the Jaylen Brown/Jayson Tatum duo, doing so for one of the best players in the NBA would make plenty of sense. Tatum and Antetokounmpo would be an elite duo and would certainly be the favorite to come out of the weak Eastern Conference next season.

Why the Trail Blazers do it

The Trail Blazers want Giannis for themselves, but no one is really taking them seriously as a suitor. The Athletic's Sam Amick and Eric Nehm (subscription required) recently talked about how Giannis wants to join a contender, and Portland might not even be that with the two-time MVP. If he puts his foot down and says he won't go there, this could be a nice Plan B for Portland.

Brown would make plenty of sense in Portland. Unlike Henderson and Sharpe, he's an established player who is ready to help a team win now. Alongside Jrue Holiday and Damian Lillard, these three could wreak havoc on both sides of the ball, matching up with other guard-heavy teams in the West, such as the OKC Thunder and Los Angeles Lakers.

Stay tuned for more Milwaukee Bucks analysis.

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