If the Milwaukee Bucks engage in any trade conversations with the Portland Trail Blazers, getting back at least some of their own draft capital must be the first order of business. Portland owns Milwaukee’s first round draft pick in 2029 outright and pick swaps in 2028 and 2030 from the Damian Lillard trade in 2023. Reclaiming any of those picks would be a great move.

Bucks could certainly use some of their picks back

Rumor has it that the Milwaukee Bucks are big game hunting, and Jerami Grant is among the targets on their wish list. That is according to NBA insider Jake Fischer (subscription required), who noted that Milwaukee’s interest in the forward has spanned years at this point. Getting Grant could possibly help, but a deal would be more enticing if the Bucks got some of their capital back simultaneously.

Right off the bat, the 2029 first-rounder is likely off the table entirely. With rumors swirling that Giannis Antetokounmpo might not be with the Milwaukee Bucks much longer, which would send Milwaukee spiraling into a dramatic rebuild, Portland knows that draft pick is a potential gold mine. However, the swaps in 2028 and 2030 are likely much more attainable in the right package.

Again, with Giannis’ future uncertain, regaining control of at least some of their draft capital would be a good move for Milwaukee’s future.

The Milwaukee Bucks may hold power in getting it in negotiations as well. With over $102 million left on his contract over the next three years, the Bucks could lift a weight off Portland’s shoulders in a deal where they take Grant and give them players with deals that expire sooner. Furthermore, Grant is currently battling Achilles tendonitis, making him all the more risky to pay at that particular price.

Trading for Jerami Grant shouldn’t be Milwaukee’s Plan A to buff up this roster. He’s a quality player, but his contract is massive, he’s dealing with Achilles issues, and he might not raise their ceiling too much compared to Kyle Kuzma, who was putting up similar numbers in Washington before coming to Milwaukee via trade. If the Bucks want to go big, they may have to think even bigger than Grant.

These two teams clearly have familiarity from the Damian Lillard trade, and it won’t be surprising if they engage in talks before the February NBA Trade Deadline. However, if the Milwaukee Bucks plan to take on Grant’s contract and injury concerns, they must make sure they are not getting fleeced in any possible trade.

Stay tuned for more Milwaukee Bucks analysis.