The Celtics Would Be Wise To (At Least) Consider Damian Lillard
Boston's savvy contract offloads have stabilized the present — but it's time to start planning for the future, too
Trimming salary, dodging luxury tax bullets, and stockpiling second-round picks has defined the Boston Celtics’ summer — a strategy that’s already rewarded incoming ownership led by Bill Chisholm.
Jrue Holiday and Kristaps Porzingis — pivotal pieces in the 2024 Celtics championship run — were the first sacrificial lambs in a cost-cutting effort that slashed Boston’s projected salary and luxury tax bill from $540 million to $280 million. Brad Stevens had little choice but to strike deals with the Portland Trail Blazers and Atlanta Hawks to proactively work toward getting the franchise beneath the second apron. It hasn’t netted much cause for optimism, yielding only Anfernee Simons, Georges Niang and three second-round draft picks.
While it has reduced the roster cost, which wasn’t feasible beyond its two-year inception, it hasn’t moved the needle much toward the next Larry O’Brien Trophy. With options in Boston running dangerously thin, and Jayson Tatum’s return timeline still uncertain following surgery to repair a ruptured right Achilles tendon, Stevens will need to tap into his creativity to thrift hunt for bargains.
Nine-time All-Star Damian Lillard (abruptly) emerged as a candidate following the 34-year-old’s stunning release from the Milwaukee Bucks.
Lillard will soon become a free agent and will collect the remaining $113 million of his contract, allowing the Celtics to incorporate some excitement into their mundane offseason. Similar to Tatum’s situation, Lillard, too, is expected to miss most if not all of next season while recovering from a torn Achilles suffered in April. So while it wouldn’t be a signing with immediate benefits, it could be a move calculated to bolster Boston’s title odds upon Tatum’s return to restore the organization’s place as the top dog in the Eastern Conference come the 2026-27 season.
Theoretically, it wouldn't cost the Celtics much to land Lillard. However, that’s also dependent on whether or not Lillard’s primary motive is maximizing his earning potential. The Bucks are already on the hook until 2029, so whatever Lillard earns — whether from Boston or elsewhere — would only be an appetizer added to the 13-year veteran’s plate. The Celtics, if able to get back under the second apron, could put together an incentivizing pitch for Lillard to join forces with Tatum, Brown and Derrick White, all while Milwaukee funnels $22.5 million into Lillard’s bank account for the next five years.
It’s not exactly a Bobby Bonilla situation, per se, but it’s pretty damn close.
Lillard has checked nearly every box on the path to a Hall of Fame career. He’s a seven-time All-NBA selection, a member of the NBA’s 75th Anniversary Team, and ranks fourth all-time in 3-pointers made — trailing only Stephen Curry, James Harden, and Ray Allen. But the one glaring omission from Lillard’s résumé is a championship. The Bucks gave Lillard a golden opportunity to chase that elusive title alongside Giannis Antetokounmpo, but the experiment fell well short of expectations.
Through 131 games with Milwaukee, Lillard averaged 24.6 points on 43.4% shooting from the field and 36.4% from three, with 4.5 rebounds and 7.0 assists. While his offensive output remained in line with what made him a star in Portland, it wasn’t enough to offset the defensive shortcomings that plagued the Bucks over the past two seasons. This wasn’t Mike Budenholzer’s drop-coverage system anymore; it was Doc Rivers and a patchwork redemption crew trying to stay afloat in a brutal contender landscape with fierce competitors like Boston.
“A team like this, you know, they feed off (mistakes),” Lillard said after Milwaukee’s first matchup against the Celtics last season, per CLNS Media. “They get a stop. They get a steal. They get out. They run. They’re hitting threes. And that’s the game that they wanna play. … And that’s what they do best.”
Before long, the clock could be ticking on “Dame Time” reaching the NBA Finals, so getting ahead of a Carmelo Anthony-style ring chase would be ideal.
Instead of sharing the backcourt with Gary Trent Jr. in Milwaukee, Lillard’s long-range shooting and court vision could pair with White’s two-way efficiency to help fill the void left by Holiday, his former running mate. Lillard’s logo threat will keep defenses on their toes and add a variable that teams didn’t need to account for when preparing their schemes for the Celtics over the past two seasons.
Tatum, Brown, and White are elite on-ball defenders, but the real question — which Stevens and the front office have until 2026–27 to solve — is at starting center. As for Lillard, his defensive limitations wouldn’t be nearly as exposed in Boston’s system, thanks to the team’s strong perimeter defense. The Celtics are built well enough to let Lillard be himself — the version that made him deadly in Portland — while giving Joe Mazzulla a shooter perfectly suited for his Mazzulla-ball philosophy.
It’s hard to imagine Joe Mazzulla walking away from his 3-point-heavy philosophy anytime soon, and even harder to picture a player of Lillard’s caliber becoming available under similar conditions. So why not capitalize? Why not show the fanbase — and Tatum and Brown — that even with budget cuts, the ultimate goal remains raising banners? Acquiring Lillard wouldn’t cost Chisholm an arm and a leg like retaining Holiday and Porzingis would. It would just take some creative roster maneuvering to slip back under the second apron.
Tatum’s injury all but confirmed that 2025–26 will be a throwaway season for the Celtics. Sure, Brown, White, and Payton Pritchard might keep the team from sinking to the bottom of the East, but then what? Sneaking into the playoffs with a thinned-out depth chart isn’t exactly inspiring, and early signings like Luka Garza and Josh Minott aren’t promising either. When Tatum is finally ready to return at full strength, it’s going to take much more to reignite a real title push.
Motivation won’t only fuel Tatum, it’ll propel Lillard, too.
Lillard’s hunger for a taste of first-time glory and Tatum’s urge to put the league on notice, again, and re-establish the Celtics as the team to beat, creates a formula few teams ever find. Stevens no longer has the blank check Wyc Grousbeck handed him two offseasons ago, and while Boston’s current reset doesn’t scream “Banner 19” for next season, it opens the door to reimagining the blueprint — one that could once again flood TD Garden in champagne and confetti.