Should the Celtics trade for Damian Lillard? Weighing the pros and cons

Damian Lillard is a top-10 player, but how risk-averse will a new Celtics front office be if he becomes available?

Damian Lillard
What would be the pros and cons of trading for Damian Lillard for the Celtics? AP Foto/Steve Dykes


The Danny Ainge era of Celtics basketball will be defined by the championship team he built in 2008, and perhaps also by his astute assessment of Jayson Tatum’s potential if he continues to blossom into an MVP candidate. 

But inevitably, any conversation about Ainge turns to his trades — both the ones he completed and the ones he reportedly came close to completing. Proponents of Ainge’s work will note he acquired a championship team via trade. His detractors will bring up the more recent rumors that swirled and eventually dissipated around Jimmy Butler, Paul George, Kawhi Leonard and perhaps even James Harden. 

The Celtics have new hands at the wheel after Ainge retired and left the keys for Brad Stevens, but the trade speculation remains. This time, the big name is Trail Blazers guard Damian Lillard.

To be clear: Nothing reliable has tied Lillard to the Celtics — or even Lillard to trade rumors at all — at this stage. The Athletic’s Shams Charania reported that teams in big markets are monitoring his situation and will be ready to bid if he becomes available, but that should come as little surprise. Lillard is one of the best players in the NBA, and his brief playoff run this year helped cement that designation (and hammered home the Blazers’ roster contruction issues). If the Blazers decide to move Lillard, it will be a major talent shift and plenty of teams will want to be involved.


Should the Celtics be one of them? Here’s a closer look at some potential pros and cons, many of which apply to any other superstar who becomes available.

The Pros

Most importantly, the Celtics would be getting a no-holds-barred superstar. Lillard averaged 28.8 points and 7.5 assists per game last season while shooting 39.1 percent on a staggering 10.5 3-point attempts. When he catches fire, he’s one of the league’s most electric players. Steph Curry has no equal as a shooter, but Lillard is a worthy challenger. 

Lillard’s fit wouldn’t be immediately perfect since the Celtics still employ Kemba Walker, but that’s not a real concern. Acquiring a player of Lillard’s caliber is Step 1. Making the roster fit around Lillard is Step 2. 

Meanwhile, Lillard’s fit next to Jayson Tatum would be glove-like. Like Tatum, Lillard is a pick-and-roll master who dominates with the ball in his hands. Tatum excelled this season as a 1A superstar, but he struggled in the playoffs when the Nets triple-teamed him. The absolute best of luck to any team hoping to double- or triple-team Tatum with Lillard confidently pulling 3-pointers from 32 feet. 

Another factor: The Nets turned themselves into a super team by trading for James Harden when other teams (including the Celtics) weren’t willing to do so. What if the Sixers trade for Lillard and pair him with Joel Embiid, or the Heat find a way to put together Lillard, Jimmy Butler and Bam Adebayo? The Eastern Conference gauntlet could become even more difficult.


Finally, Lillard has an intangible authenticity that other players around the league seem to respect. When Lillard percolates, players turn into fans flocking to Twitter to post awed emojis and comments. 

Tatum seems to be approaching that status as well. The Celtics won’t have cap space for a while, but Lillard and Tatum could eventually turn the Celtics into an attractive landing spot for free agents if they enjoy playing together in Boston.

The Cons

But what if they don’t?

Lillard will turn 31 next month, and he will earn $43 million per year on average through 2025. If things go poorly, the Celtics won’t exactly be nimble.

Trading for Lillard would unquestionably cost Jaylen Brown, since other bidders will offer enough to trump any combination of Marcus Smart, young players and picks. The Celtics’ ace in the hole is that they have two star wings who can grow together, but if the right superstar becomes available, they also have a young star of Brown’s caliber who would be an intriguing 1A option on another team. If the Celtics trade Brown, they will be locked into the team they created for the foreseeable future.

The Lillard/Tatum pairing makes sense. So did the combination of Kyrie Irving, Gordon Hayward, Jaylen Brown, Al Horford and Tatum, which famously combusted. Unlike the 2018-19 team, which produced a core of Jayson Tatum and Jaylen Brown when the other three players left in free agency, the Lillard/Tatum pairing would have no Plan B.


Maybe Lillard and Tatum would be a perfect pairing and the Celtics would have the offensive firepower to compete with the Nets while Tatum is still six years younger than their youngest star. Maybe they flame out and all that’s left of the decade-long contender Danny Ainge appeared on the brink of sculpting is Aaron Nesmith and Romeo Langford, while Tatum and Brown rack up awards and victories elsewhere. 

That’s about as high-risk, high-reward as a basketball scenario gets.


At this stage, it still seems unlikely that Lillard will become available this summer.

If he does, how much risk are the Celtics are willing to take on in their first offseason under Brad Stevens? Stevens might look dispassionately at a roster he didn’t build and see foundational ways he believes it can be improved. He also might see two young stars who have done a lot for the franchise and wonder what they could be with a real offseason and some veteran help on the edges. 

In either case, Stevens could get an intense early test. As was often the case under Stevens’ predecessor, the Celtics could be one of the more interesting stories in the league when the offseason begins.

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