The Damian Lillard Trade Changes Everything for the Milwaukee Bucks

The Damian Lillard trade saga is finally over—and it ended with a stunning climax: The seven-time All-Star is headed not to the Miami Heat, nor the Toronto Raptors, but instead to the 2020-21 champions. After suffering a humiliating upset as the no. 1 seed in the first round of the 2022-23 NBA playoffs, amid burbles of discontent from franchise icon Giannis Antetokounmpo, the Milwaukee Bucks are the surprise winners of the Lillard sweepstakes.

Wednesday’s three-team shocker came together like sleep, or love: slowly—extremely slowly, with months of stagnation and only redundant rumors about the Heat—and then all at once. Now, Lillard is headed to Milwaukee. Jrue Holiday and potentially three unprotected future firsts (a 2029 pick, and swap rights in 2028 and 2030) are headed from Milwaukee to Portland, where they’ll be joined by Deandre Ayton and Toumani Camara, via Phoenix. Jusuf Nurkic, Grayson Allen, Nassir Little, and Keon Johnson are all headed to Phoenix to round out the deal.

Assuming Lillard suits up for his new team, despite reported threats to sit out if he were traded anywhere other than Miami, the Bucks will now add one of the NBA’s best offensive players to the league’s best defensive frontcourt. They’ll signal as strongly as possible to Giannis that they’re “going for a championship” and “on the same page” as he is, as he contemplates whether to sign a new, three-year extension. And they’ll undercut other Eastern Conference rivals—Miami? Boston? Philadelphia? New York?—that hoped to either add Lillard this summer or poach a discontented Giannis soon after.

In essence, the Bucks dove all in to sacrifice future flexibility in both the draft and cap room, but in so doing they might have solved their greatest problems in both the present and future.

The first answer comes from Lillard’s own offensive prowess; it’s impossible to overstate his greatness as a lead ball handler. Last season, Lillard ranked first among all players in the offensive component of EPM, first in RPM, second in BPM, and second in RAPTOR. You don’t need to know what those acronyms stand for, other than that they’re all advanced stats that measure overall offensive impact. And Lillard was either first or second behind Finals MVP Nikola Jokic in every single one.

Or, if you care more for traditional stats, Lillard averaged a career-high 32 points per game—the most for any player in league history who moved on to a new team the next season—before being shut down for, uh, “right calf tightness” as Portland coincidentally sought better draft position. He’s a career 37 percent 3-point shooter on high, difficult volume; an elite pick-and-roll creator who should form an immediately dominant thunder-and-lightning pairing with Giannis; and one of the NBA’s best clutch performers. “Dame Time” is both a nickname and a solution for the Bucks’ greatest weakness, as they so often fumbled late-game possessions in the postseason.

This megadeal represents a fascinating tactical reversal for the Bucks at the point guard position. The outgoing Holiday is one of the NBA’s best defensive guards—he was an All-Defensive honoree in all three seasons he played in Milwaukee—but an erratic postseason scorer. Over the last three postseasons, Holiday ranked 42nd in postseason true shooting percentage out of 43 players who attempted at least 300 shots, ahead of only noted chucker Dillon Brooks.

Lillard, meanwhile, is an offensive savant but a disengaged defender at best. It’s not his fault, necessarily, that Portland has ranked 27th or worse in defensive rating, per Cleaning the Glass, in each of the last four seasons, but as a skinny 6-foot-2 guard who focuses much of his energy on the other end, Lillard certainly didn’t help stem that defensive slide.

Yet after this spring’s shocking first-round flameout, it’s not a huge surprise to see Milwaukee pivot so drastically. Lillard’s half-court creation and clutch scoring can also help the Bucks reduce their reliance on Khris Middleton, whose health and effectiveness after a succession of injuries are now in question. And Milwaukee can bet that a frontcourt with Giannis and Brook Lopez will compensate for any defensive backslide in the backcourt.

The offense-for-defense swap comes at a tremendous cost, both now and in the future. The Bucks already didn’t control any of their next four first-round picks—they still owe New Orleans two swaps and two outright picks from the previous Holiday trade—and now they’re out three more, meaning they can’t use a future first to upgrade their roster for the next two years, at which point their 2032 (!) pick will be available to deal.

And Lillard’s contract complicates Milwaukee’s cap sheet, just as more onerous luxury tax penalties arrive with the new CBA. There’s a reason the market for a player with Lillard’s talent was so slow to develop: He’s a small 33-year-old guard who’s owed an estimated $122 million on a two-year extension that doesn’t kick in until 2025-26. If the Bucks don’t parlay this boost into another Finals berth soon, there’s a chance that Giannis will still leave, and they’ll be without any picks and with a $63 million bill for a 36-year-old Lillard several years down the line.

But if the Bucks hadn’t made this move, and if they’d suffered another premature postseason exit next spring, they might have found themselves without Giannis anyway. It’s impossible to know whether Milwaukee would have taken such a big swing if not for Giannis’s recent comments about potentially seeking a new team, but if it was the two-time MVP’s intention to force his team’s hand, the strategy certainly worked.

For Portland, meanwhile, this deal came to fruition after months of no movement. The Trail Blazers will almost definitely flip Holiday to another team because a rebuilding squad has little need for a 33-year-old who’s up for a contract extension this season, which would turn their ultimate haul for Lillard into a handful of picks, plus Ayton, plus the elimination of Nurkic’s remaining three years and $54 million.

(On the Nurkic front, I’ll let my colleagues tackle the ripple effects of this blockbuster and analyze Phoenix’s end of the deal in more depth. But suffice it to say I don’t think Nurkic is actually the proper “defensive anchor” that new coach Frank Vogel can “build his defense around.” Expect a few Suns games to end with scores in the 150s this season.)

All along, Portland signaled that it didn’t want to add a guard as the cornerstone of any Lillard trade, because the Blazers want to build around their youthful backcourt trio of Anfernee Simons, Shaedon Sharpe, and no. 3 pick Scoot Henderson. Ayton has plenty of warts, including both his stagnated skill set and effort level, but he’s still a 25-year-old former no. 1 pick with meaningful playoff success on his résumé, and it’s understandable that Portland would prefer his change-of-scenery upside to that of Miami’s Tyler Herro.

With plenty of extant backcourt scorers plus a new center, the Blazers could spend the 2023-24 season as a sneakily entertaining League Pass watch. Lillard’s new team, of course, occupies a much loftier perch. The Bucks were the East’s no. 1 seed last year—thanks to some unsustainable point differential luck—but the dispiriting playoff loss from the NBA’s oldest roster suggested they no longer quite belonged in the league’s top tier of title contenders.

Yet the Bucks relied on a proven formula to return to co-favorite status, along with stalwarts like the defending champion Nuggets and Celtics. The last time the Bucks suffered an early playoff exit, in 2020, they responded by trading a smorgasbord of future picks and swaps for Holiday; that gamble paid off with the franchise’s first title in 50 years. If Lillard fits as seamlessly as it appears he will on paper, they won’t have to wait nearly so long for the next one.