Jun 13, 2026 12:32 AM

A complex three-team blockbuster could leverage Milwaukee’s draft picks to land Jaylen Brown in Rip City, pairing the All-Star wing with Damian Lillard to ignite a championship-caliber rebuild.

Ever since the Giannis Antetokounmpo trade talks really began ramping up, I've held the opinion that the Portland Trail Blazers can offer the Milwaukee Bucks the most in any sort of return package. 

Sure, the Miami Heat may be able to string together a better package of players, but the Blazers possess the key needed for the Bucks to rebuild: their own draft picks. 

Portland holds Milwaukee's 2028 and 2030 swap rights, two picks in years when it would be highly unlikely to see the Bucks contend after losing a player of Antetokounmpo's caliber. 

But the "Greek Freak" has expressed a desire to remain in the East, likely ruling the Blazers out as a destination. So how do we resolve this? 

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It's actually quite simple. Below is a realistic framework, courtesy of Jake Weinbach, that gives Milwaukee their picks back while shipping Antetokounmpo to the Northeast and landing Jaylen Brown in Rip City. 

Celtics receive: Giannis Antetokounmpo

Trail Blazers receive: Jaylen Brown

Bucks receive: Jerami Grant, Shaedon Sharpe, Yang Hansen, No. 27 overall pick (via BOS), 2027 first-round pick (via POR), 2028 first-round pick (via ORL from POR), 2029 first-round pick (most favorable of POR/BOS/MIL from POR), 2028 and 2030 first-round swaps (via MIL from POR)

In this scenario, Milwaukee does lose out on Miami's package including Tyler Herro, Jaime Jaquez, Kel'el Ware and multiple first-rounders, but the Bucks do manage to regain some sort of foundational safety net should they sit near the bottom of the East moving forward. 

It makes sense for Milwaukee, which obviously matters the most. But it actually makes sense for all three parties involved. 

Boston pairs Antetokounmpo with Jayson Tatum in an attempt to fight for each's second NBA Title, while Portland assembles a backcourt of Damian Lillard and Jaylen Brown to complement its exciting young core. 

Assuming Lillard and Brown are tabbed as the starters in the backcourt, that would mean the Blazers get to bring Shaedon Sharpe and Jrue Holiday off the bench. That's incredible depth. 

Of course that's assuming both of those guys would be okay with coming off the bench, but them doing so would allow Portland to contend at the top of the West as soon as next season. 

If not, Holiday and Sharpe could even be used in a separate trade down the line to further solidify the Blazers' roster as one ready to win now versus later. 

Once Brown is in Portland, nothing will be off the table. 

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