Context: What’s the Lillard–Simons Connection?0-1Damian Lillard, the nine-time All-Star guard, was waived by the Milwaukee Bucks in early July 2025 after suffering a torn Achilles during the first round of the 2025 playoffs. Milwaukee stretched his remaining contract (approximately $113 million) over five years, effectively freeing both roster and cap space to sign Myles Turner .628-0With all his money guaranteed by Milwaukee, Lillard became a free agent able to sign with any team—including Boston—for a minimal salary, while still collecting his full contract payout from Milwaukee .882-0Meanwhile, Boston acquired Anfernee Simons in the Jrue Holiday trade. Simons carries a substantial expiring contract (~$100 M over four years) and the Celtics are reportedly seeking to flip him to shed salary .Why Celtics Are Now the Front-Runners for Lillard
🔧 1. Cap Flexibility & Simons Trade
1158-0The Celtics’ ability to sign Lillard via the taxpayer mid-level exception is contingent on clearing Simons’ contract. If Boston trades Simons, they gain the necessary cap room (approx. $5.7M) to pursue Lillard while keeping under the luxury tax threshold .
1564-0Bleacher Report’s Greg Swartz praises this setup as a sweepstakes scenario where Boston can land a superstar at minimal cost—“The last time the Celtics got a veteran point guard from the Milwaukee Bucks, it ended pretty well”, referencing Jrue Holiday and the 2024 title win .
🗣️ 2. Jayson Tatum’s Personal Push
1865-0With both Tatum and Lillard recovering from Achilles injuries, Celtics star Jayson Tatum has reportedly been actively recruiting Lillard to Boston. This makes the franchise a genuine emotional and strategic fit .
2157-0Some league sources affirm that Boston remains high on Lillard’s list of preferred destinations—his relationship with Tatum providing mutual rehab support and camaraderie .
🧠 3. Lillard’s Own Flexibility and Gameplan
2368-0Lillard has publicly framed the opportunity as a “jackpot”, because signing with any team will not reduce his guaranteed payout from Milwaukee. He appears to be selecting a team based on rehab environment, fit, and long-term vision rather than salary .
Why Favor Boston Over Other Interested Teams?
2717-2Lillard’s return to Portland on a three-year $42 M deal on July 19, 2025 means he has ties to his former team geographically and emotionally—and may prefer rehab stay in Portland .3287-0League sources especially highlight Boston’s ability to structure a deal through Simons’ re‑trade. The Warriors or Lakers don’t hold such flexibility unless they engineer comparable roster moves .3534-0Boston’s front office, led by Brad Stevens, is known to actively explore moving Simons for cap relief―a necessary move to complete the Lillard signing .
Breaking Down the Financial Mechanics
| Item | Detail |
|---|---|
| Simons’ Contract | |
Strategic & Roster Fit Considerations
Long-term Vision
3740-8Boston may endure a transitional 2025‑26 season—Tatum and Lillard both sidelined—but the projected 2026‑27 core (Tatum, Lillard, Brown, White) could form one of the most potent offensive trios in the league .
Short-term Sacrifices Acceptable
4888-0Bern in mind: Boston would carry two injured players, occupying roster spots and impacting depth. Yet analysts note that if Boston opts to “tank” the 2025‑26 campaign or focus solely on rehab synergy, the potential long-term payoff outweighs the temporary loss .
Community & Insider Buzz5240-0Bleacher Report highlights that Boston’s interest is tied to Simons trade flexibility and the strategic narrative of “getting him cheap and integrating him with Tatum” .5467-0Boston Celtics Reddit chatter reinforces that the front office is actively shopping Simons while cultivating his trade value .
Possible Headwinds & Unknowns5635-0Health Risk: At age 35, recovering from a torn Achilles always carries risk. Critics argue Lillard’s prime may be behind him, though his resolve and professionalism remain respected 5899-1Lillard’s Preference: Although Boston appears the logical destination, Lillard might opt to rehab in Portland with his family and community support—he reportedly wants proximity to his kids . SummaryThe Celtics have emerged as clear favorites to sign Damian Lillard, contingent on their ability to flip Anfernee Simons and clear cap space.Their edge comes from financial flexibility, a strong internal push from Jayson Tatum, and a strategic timeline that looks past 2025‑26 toward immediate contention in 2026‑27.Other teams (Warriors, Lakers) remain in the mix, but Boston’s roster mechanics and front-office willingness to absorb short-term risk make them the premier candidate.Boston’s plan is a bold bet: sign Lillard where he rehab together with Tatum, keep pace through 2025‑26, and merge elite star power for a championship run started in 2026‑27.
If Simons is traded and the MLE is activated, we’ll likely see Lillard in green—fully embedded in Boston’s next era.
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