Jayson Tatum Reportedly Recruiting Damian Lillard to Join Celtics

Here's what a Celtics' deal for Damian Lillard might look like, plus an evaluation of each potential path, including not trading for the seven-time All-Star.

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On NBA Today, Marc Spears of ESPN and Andscape shared he's heard Jayson Tatum is recruiting Damian Lillard to join the Celtics.

Less than a month ago, Bleacher Report's Chris Haynes stated it's "pretty safe to say" the seven-time All-NBA guard isn't interested in taking his talents to Boston. But perhaps Tatum's sales pitch proves effective.

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Saturday, in the aftermath of Lillard's trade request, Trail Blazers' GM Joe Cronin conveyed, "We have been clear that we want Dame here, but he notified us today he wants out and he'd prefer to play someplace else. What has not changed for us is that we're committed to winning, and we are going to do what's best for the team in pursuit of that goal."

The seven-time All-Star is 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 he has a $63.2 million player option for 2026-27.

While NBA stars often end up where they want, which in this case is Miami, it would be foolish of Portland to trade him for a return it finds underwhelming.

Boston "only" needs a little over $41 million in outbound salary to make the math work in a deal for Lillard.

That means the Celtics could acquire him without parting with Jaylen Brown. A package of Malcolm Brogdon, Robert Williams, Payton Pritchard, Justin Champagnie, three first-round picks, plus pick swaps, could top an offer from the Heat centered around Tyler Herro joining the Trail Blazers or going elsewhere in a three-team deal.

However, it's unlikely that proves the best proposal Portland receives. Boston could bolster it by including Derrick White, though.

That begs the question, can Lillard, Brown, Tatum, and Kristaps Porzingis, co-exist at a championship level?

The Celtics would have the most talented top four in the NBA, and three of them are or are about to get taken care of contractually. The fourth is Tatum, who doesn't have to worry about the franchise's willingness to offer him a supermax extension next summer.

The two-time All-NBA First Team member may have to sacrifice the most in terms of touches and shots for that one-year experiment to produce Banner 18.

Boston could also avoid that potential problem by trading Brown rather than extending him. The latter would make him ineligible to get moved for a year.

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Perhaps, the Trail Blazers are willing to add him, hoping he'll stay for the chance to be the top option while flanked by promising young players Shaedon Sharpe and this year's third overall pick, Scoot Henderson. They also have Jerami Grant and could move Anfernee Simons to have a more balanced roster. Or this could turn into a three-team deal where the two-time All-Star goes elsewhere.

Perhaps, recalibrating so the team's top tandem features a wing and a lead-guard proves more effective than what the Celtics already have and gets more out of Porzingis.

Trying to keep a window of contention open as long as possible can cost a team its best chance at a championship. Swinging deals for Kevin Garnett and Ray Allen "only" led to one title, but the former resuscitated the franchise.

But trading a 26-year-old All-NBA wing entering his prime for a six-foot-two guard, who's about to turn 33, is a defensive liability, and is on a sizable contract, could backfire.

While there's a strong argument for remaining patient with a team led by Tatum and Brown, who have steered Boston within two wins of a title and to the Eastern Conference Finals in four of their first six years together, giving them at least two more cracks at the Larry O'Brien Trophy as the former, 25, reaches his prime, another layer of this is the organization may have already decided two players taking up roughly 70 percent of its cap space is untenable.

If that's the case, knowing it intends to part with Brown before his and Tatum's extensions come on the books in 2025-26 could soften the Celtics on trading the former to acquire Lillard.

Further Reading

Jordan Walsh Discusses His First Celtics' Practice, Summer League Goals, and a Grant Williams Anecdote

Celtics Sign Forward Oshae Brissett

Celtics Reportedly Interested in Signing Terence Davis

Celtics, Kristaps Porzingis Agree to 2-Year, $60 Million Extension

Kristaps Porzingis on Teaming with Jayson Tatum and Jaylen Brown: 'I Think It Can Be a Great Combination'

Grant Williams Discusses Marcus Smart's Departure, Free Agency, and Recovery from Hand Surgery

Brad Stevens Shares What Compelled Celtics to Trade for Kristaps Porzingis

Brad Stevens Discusses Difficult Decision to Trade Marcus Smart: 'He'll Always Have Boston'

Marcus Smart Felt "Shock" and "Hurt" Over Trade from Boston Celtics

Marcus Smart Discusses Celtics' Identity, Relationship with Jaylen Brown, Boston's Coaching Hires, and Pursuit of Banner 18