Bucks News: Trade Pitch Sees Damian Lillard Flipped for $129M Former Champ

It's a risky, if interesting, move for Milwaukee.

Dec 6, 2024; Boston, Massachusetts, USA; Milwaukee Bucks guard Damian Lillard (0) controls the ball during the first half against the Boston Celtics at TD Garden. Mandatory Credit: Bob DeChiara-Imagn Images / Winslow Townson-Imagn Images

At 34 and with a clearly declining first step, Milwaukee Bucks All-Star point guard Damian Lillard is no longer quite the clutch All-NBA superstar he was during his Portland Trail Blazers prime, which at its zenith saw him leading a slightly underqualified 2018-19 squad past the then-rising Denver Nuggets in a hard-fought Western Conference second round contest and all the way to a West Finals date with the then-reigning champion Golden State Warriors, at that point loaded with All-Stars Kevin Durant, Stephen Curry, Klay Thompson and Draymond Green, all still in their primes. The Trail Blazers were promptly swept.

Lillard has never made it past the first round since.

When he joined All-NBA Milwaukee power forward Giannis Antetokounmpo, pundits considered the new-look Bucks to be a fringe title contender heading into the 2023-24 season. Without All-Defensive guard Jrue Holiday (offloaded in the deal to nab Lillard) and with former three-time All-Star small forward Khris Middleton declining, the team collapsed defensively along the perimeter. The Bucks still finished with a 49-33 record and the East's No. 3 seed last year, but they were trounced in the first round by the underdog Indiana Pacers, thanks in part to matchup issues and in part to an injury that cost Antetokounmpo the entire series.

This year's Bucks are thoroughly mediocre at 12-11. Should the team move on from the Lillard experiment and free up some cap space to build more around Antetokounmpo?

Fran Leiva of Fadeaway World submitted a fascinating trade pitch recently to both boost the Houston Rockets' upside and bolster the Bucks' depth.

"First off, Giannis is reportedly off the table for Houston," Leiva offers. "The Rockets don’t want to give up their entire young core to land him, which makes sense since gutting the team for one superstar doesn’t fit their timeline. But Dame? That’s a much more realistic target."

Lillard is earning $48.8 million this season, and has two years and an estimated $112.6 million headed his way through 2026-27, when he'll be 36 — ancient for a point guard.

"Pulling off a deal for Dame could look something like this: you send out Fred VanVleet, a couple of non-starters from the young core (think guys like Tari Eason and Reed Sheppard), and a big pile of future draft picks," Leiva writes. "That way, you keep your key guys like Jalen Green and Alperen Sengun intact while still landing a superstar. Dame would give the Rockets an elite scorer and playmaker who could take over in clutch moments, something they’re still missing. Plus, with his experience, he’d be the perfect mentor to help this young team learn how to win."

It's a fascinating proposal, and one that could at least help solve the Bucks' bench woes. But would VanVleet, Eason and Sheppard together comprise enough to provide comparable value for Lillard, in combination with a refreshed draft arsenal? Would Milwaukee be willing to probably take a step back this season, with an eye towards the future?

"Overall, trading for Damian Lillard could be the kind of bold move that solidifies the Rockets as legit contenders," Leiva concludes. "He’s a much more realistic option than Giannis, and the Bucks might be willing to listen if the Rockets come with a strong offer. It’s not every day you get the chance to add a player of Lillard’s caliber without blowing up your entire team. If Houston plays their cards right, Dame Time could be the next big thing in H-Town."

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