After Jaylen Brown's Extension, Could Celtics Complete Blockbuster Deal for Damian Lillard?

In response to NBA's league-wide memo about him saying he only wants to join the Heat, Damian Lillard and his agent Aaron Goodwin assured teams wherever he's traded will get his best effort.

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The Celtics accomplished the task at the top of their off-season to-do list this week, finalizing a record-setting veteran supermax extension with Jaylen Brown. The deal projects to be worth $304 million over five years, with next season's league salary cap determining where it ultimately lands.

Earlier this summer, Boston shook up the core of its roster, sending Marcus Smart, the longest-tenured player on the team and someone who helped the franchise reach the playoffs each of his nine years in Kelly green, to the Grizzlies in a three-team trade in which it acquired Kristaps Porzingis.

But while head coach Joe Mazzulla confirmed Wednesday, after the press conference where Brown signed the most lucrative contract in NBA history, held at MIT, home to the Bridge Program, developed by the All-NBA wing's 7uice Foundation, which works with the Community Biotechnology Initiative at the MIT Media Lab to provide science and technology opportunities for children in Boston's underserved communities, Derrick White will be the Celtics' starting point guard in 2023-24 perhaps they still have a summer blockbuster in store.

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According to The Athletic's Shams Charania, the NBA recently sent out a memo to all 30 teams regarding Damian Lillard's stance about only wanting to join the Heat.

NBA sent a memo Friday to all 30 teams about Damian Lillard’s trade request and the stance that he only wants to play in Miami. Reporting details on @TheRally: pic.twitter.com/xkgMfcTeqI

— Shams Charania (@ShamsCharania) July 28, 2023

"Any player (or, for clarity, any player representative or person acting with authority on behalf of a player) who publicly expresses a desire to be traded to another Team shall be subject to a fine and/or a suspension," states the NBA's new collective bargaining agreement. "The maximum fine that may be imposed by the NBA on a player pursuant to the foregoing shall be $150,000."

The seven-time All-NBA guard and his agent, Aaron Goodwin, have responded to that league-wide memo by assuring teams, regardless of where he ends up, that organization will get his best effort, per Barry Jackson of the Miami Herald.

The idea Lillard would suddenly turn into a bad teammate on or off the court if he didn't end up in Miami always seemed like a bluff. But the NBA, doing more than ever to promote parity, has blunted the only leverage the seven-time All-Star had.

And with the Heat's offer not enticing enough to get a deal done yet, compelling Trail Blazers general manager Joe Cronin to convey Portland intends to remain patient as it works to do what's best for the franchise, the door is open for Boston to strike.

Brown's ineligible to get traded this season. And the Celtics seemingly didn't have an appetite for parting with him to acquire a six-foot-two 33-year-old point guard on the books for $45.6 million for the coming campaign, $48.8 million for the 2024-25 season, an estimated $58.5 million for 2025-26, and who has a $63.2 million player option for 2026-27.

Furthermore, if Boston sent the two-time All-Star elsewhere this summer, rather than signing an extension this offseason, playing out his contract would've been in his best interest. Banking on Brown staying in Portland beyond 2023-24 is a gamble the Trail Blazers were best to avoid.

Soobum Im-USA TODAY Sports

That meant a third team, with higher odds of the 26-year-old wing re-signing with, like the Rockets, would've had to get involved and supply Portland with a package of promising young players.

While that scenario's off the table, given Lillard's current franchise's lack of interest in adding Tyler Herro to a backcourt featuring Scoot Henderson, Shaedon Sharpe, and Anfernee Simons, perhaps acquiring Robert Williams, who turns 26 in October, and three first-round picks, plus pick swaps, is a proposal the Trail Blazers are more open to.

Derrick White and Malcolm Brogdon, who would also figure to be in the deal due to their salary and value, could mentor Portland's young guards and get moved later to help expedite a rebuild.

However, from this vantage point, given the durability concerns about the Time Lord, and Boston's picks projecting to be in the 20s, that seems like a very beatable offer.

And that's to say nothing about whether Jayson Tatum, Lillard, Brown, and Porzingis could mesh to form a title-winning quartet. Even if they did, the restrictive and punitive nature of the new CBA suggests this would be a short-lived experiment.

But if those factors don't scare the Celtics off, the Sixers don't offer Tyrese Maxey, and the Trail Blazers don't warm up to the Heat's proposal, Lillard taking his talents to Boston, who would have the best top four in the NBA, isn't a scenario to rule out.

Further Reading

Dwyane Wade Discusses Jayson Tatum's Next Step, Him and Jaylen Brown's Challenge, Heat Culture, Pat Riley, Damian Lillard, and Life After Basketball

Jaylen Brown Doesn't Want Celtics' Defensive Identity to 'Go Out the Door' With Marcus Smart

Jaylen Brown Wants Record-Setting Contract with Celtics to Spark Revolutionary Goals

Despite Extension, This Season Could Be Jaylen Brown and Jayson Tatum's Last Chance at a Championship Together

Why Celtics Should Enter 2023-24 Season Optimistic About Most Important Area of Improvement

Amid Negotiations with Celtics, Jaylen Brown Continues Giving Back to Community He Stars In: 'Nothing Fills My Heart More'

Intriguing Option for Celtics May Soon Become Available

Sam Cassell Discusses What Brought Him Back to Boston and What He'll Bring to the Celtics

Oshae Brissett on Joining Celtics: 'I Just Want to Go Win'

Marcus Smart Reflects on His Time with Celtics: 'I Left Everything I Had'

Evaluating Celtics' Options in Free Agency