Bucks Receive Massive Haul For Damian Lillard in New Blockbuster Trade Proposal

Milwaukee would likely pull the trigger on this deal. But would the other teams involved be so amenable?

Nov 18, 2024; Milwaukee, Wisconsin, USA; Milwaukee Bucks guard Damian Lillard (0) drives towards the basket around center Brook Lopez (11) during the fourth quarter against the Houston Rockets at Fiserv Forum. Mandatory Credit: Jeff Hanisch-Imagn Images / Jeff Hanisch-Imagn Images

Is it time for the Milwaukee Bucks to end their Damian Lillard experiment, just 14 games into their second season with the eight-time All-Star?

The Bucks flipped All-Defensive Team guard Jrue Holiday to the Portland Trail Blazers as part of their deal to acquire Lillard just ahead of the start of training camp prior to the 2023-24 NBA season. Milwaukee posted a solid-but-unspectacular 49-33 record with its new dynamic duo of Lillard and All-NBA power forward Giannis Antetokounmpo, not too shabby for a club that fired head coach Adrian Griffin midway through the season.

Under Griffin's replacement, Doc Rivers, the team secured the Eastern Conference's third seed, but was hit by injuries to Lillard and Antetkounmpo in its first round playoff matchup against the lower-seeded Indiana Pacers. The Bucks were eliminated in six games.

Milwaukee stumbled to a brutal 2-8 season start, but has rounded into form a bit more of late, after Rivers tinkered with his starting five and replaced Gary Trent Jr. with second-year shooting guard Andre Jackson Jr. The Bucks have gone 3-1 across their last four contests, improving their record to a still-bad 5-9.

One big caveat of that 3-1 run: Lillard missed all but one of those contests. In his one available game, Lillard proved relatively inefficient in Milwaukee's 101-100 nailbiter victory against the Houston Rockets Monday, shooting 6-of-18 from the field — but he also clinched the buzzer-beating, game-winning layup late.

The 34-year-old can still summon up "Dame Time" on occasion, but the 6-foot-2 Weber State product doesn't look like his All-NBA Portland prime-era self. Should the Bucks move on while they can still potentially extract value from him?

Greg Swarz of Bleacher Report submits an intriguing three-team trade pitch that could help Milwaukee add some depth, cap flexibility and more draft equity.

Los Angeles Lakers Receive: PG Damian Lillard

Milwaukee Bucks Receive: G Austin Reaves, F Rui Hachimura, PG D'Angelo Russell, 2029 first-round pick (unprotected via Lakers)

Detroit Pistons Receive: F/C Christian Wood, 2025 second-round pick (via Lakers)

Lillard would be yet another past-his-prime former superstar point guard joining incumbent All-NBA Lakers frontcourt stars LeBron James and Anthony Davis, but unlike L.A.'s doomed Russell Westbrook experience, Lillard can actually thrive off-ball but also serve as a key supplemental ball handler next to the 39-year-old James, who's been the league's oldest active player for a year. The two-man pick-and-roll game between Lillard and Davis could prove lethal. Or, like Milwaukee's two-man game between Antetokounmpo and LIllard, it could be tantalizing in flashes but not utilized nearly as frequently as it should be.

Detroit, meanwhile, would hilariously re-acquire Christian Wood (who has yet to play a game for L.A. this season as he recuperates from surgery) while also bolstering its depth.

Adding two players with real value deals in Reaves and Hachimura could be huge for building out the Bucks' depth and helping the team embark on its next era as 33-year-old Khris Middleton and 36-year-old Brook Lopez age out. Russell is on an expiring contract and could prove to be a trade chip for another club. The Bucks desperately need to replenish their asset base, so bringing back an unprotected first round pick could be huge for Milwaukee.

Would L.A. pull the trigger on such an all-in deal? Given that, in this pitch from Swarz, the Lakers are only sacrificing one pick, perhaps the team may think about it. But Reaves is a really solid player, on a really good contract, and it seems risky to offload him for an aging Lillard.

More Bucks: Milwaukee Moves Damian Lillard, Lands $120M Star in New Blockbuster Trade Proposal