Can Celtics Get Involved in the Damian Lillard Trade Sweepstakes?

The field — teams other than the Miami Heat — emerged for the first time as a potential suitors for Damian Lillard with talks between the Heat and Trail Blazers stalled, and Portland hoping to clarify its future beyond Lillard before training camp begins next week.

 

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Jake Fischer reported the Bulls and Raptors could emerge as destinations, the two teams most talked about among NBA personnel in recent weeks. Both teams carry the desperation to upgrade their top-end talent with their cores deteriorating and no clear path toward contention or tanking. The Nets sit in a similar position, with plenty to offer in hypothetical Lillard trades, though their interest hasn’t emerged in any reports. Neither has the Celtics’ officially, though Marc Spears reiterated Jayson Tatum’s courting of the star guard in an August podcast appearance, while oddsmakers pointed to the Celtics as favorites to land Lillard if he doesn’t go to Miami.

Ramona Shelburne reported that Boston expressed some interest in July, when Jaylen Brown’s contract remained available pre-extension. Brown never made sense for Portland on a one-year deal though, and Boston eventually agreed to a super-max extension with Brown without shopping him like they did a year ago. They committed to Brown, and while that seemingly eliminated Boston from any Lillard pursuit from a value perspective, Miami can’t blow Portland away either, and while the field remains cautious, the Celtics could decide to emerge as an aggressive suitor despite Lillard’s camp sending signals they would not prefer to play in Boston.

Why make such an aggressive move after already shaking up the roster to land Kristaps Porziņģis?

• Lillard, who shot 37.1% from three on 11.3 attempts per game, would perfectly fit Joe Mazzulla’s system and his gravity above the three-point line inspired the way Boston used Tatum as an aggressive spot-up shooter last year. Lillard would allow Tatum to play closer to the basket and solve some of Boston’s ball-handling concerns, Lillard posting 7.3 assists to 3.3 turnovers per game.
• As one of the league’s best players in the clutch throughout his career, Lillard would clean up some of the Celtics’ fourth quarter concerns that again undermined Boston in the postseason. Opponents outscored Boston by 11.4 points per 100 possessions in 11 clutch finishes during the playoffs.
• Consolidating players like Malcolm Brogdon and Robert Williams III, who carry injury concerns and future uncertainty with the team, will minimize some of the roster’s risks and turn them into greater certainties entering a critical year.

That last point doesn’t preclude the risks Lillard would bring to Boston, top among them his stated desire to not play anywhere except Miami. The last great point guards and star experiments alongside Brown and Tatum in Kyrie Irving and Kemba Walker didn’t work, and Lillard brings some of the size and defensive concerns, along with the miles that Walker did at 33-years-old. That all makes it improbable Boston could land him at this stage of the offseason. It’s not impossible.

Boston sits below the second apron line for one more season, and the CBA gave some leeway in trade matching this year by allowing trade matching within 110% for those teams instead of dollar-for-dollar matching beginning in 2024-25. Lillard makes $45.6-million, so the Celtics would need to send Brogdon’s $22.5-million and Williams III’s $11.6-million to reach 34. From there, Al Horford’s $10-million deal gets them within range, but Bsoton would probably prefer having a proven big man behind Porziņģis. Stacking up Payton Pritchard, Luke Kornet and Sam Hauser’s contracts gets to $8.3-million, fitting in Lillard beneath the 110% leeway.

The Celtics also own a top-four protected Warriors pick, Jordan Walsh, their draft picks in 2025, 2027, 2029 to offer outright, with swaps allows in 2026 and 2030. They’d want to retain some depth and cost-controlled players, Dalano Banton, Oshae Brissett, Svi Mykhailiuk, Jay Scrubb and Neemias Queta quickly left over as the team’s bench depth, but with four stars, staggering lineups would only leave the need for White, Horford and maybe one additional bench wing in playoff situations.

The Celtics would immediately ascend to prohibitive favorite status, and while the finances would become a concern as soon as next year, White due an extension, it’d be worth addressing that later for a near slam dunk ring. Consider that adding Lillard keeps him away from Philadelphia, Miami and Toronto.

It’s uncertain whether the Heat or Raptors would retain enough depth following a Lillard trade to seriously challenge the Celtics. The Sixers could do so by utilizing James Harden’s contract in a larger deal, allowing Lillard to join Joel Embiid. Those deals get too complicated to imagine, but Deandre Ayton emerging as a facilitating contract helps, as would Boston offering some contracts to make things work if they aren’t afraid of Lillard landing on an east contender.

In the case of Miami, Boston could take on Tyler Herro’s contract in a larger deal while sending draft picks and Brogdon’s contract out. Phoenix could use a facilitator like Brogdon in the back court, while Indiana lurks with Buddy Hield’s contract to add another sizable deal into the mix of contracts floating around ready to be moved. For what it’s worth, the Boston Globe reported that Boston isn’t actively shopping Brogdon despite uncertainty surrounding him entering camp.

The straightest and most impactful move would actually bring Lillard to Boston, and while it’s unlikely this late in the summer given his demands, the Irving trade showed nothing’s impossible. Brad Stevens has aggressively utilizes draft picks.  Boston has enough to gain this year from any percentage increase in their championship odds. Lillard solves some of their biggest challenges preventing the team from winning a title.