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As the Celtics and Jaylen Brown's camp work to hammer out the details on a five-year, $295 million veteran supermax extension, the former must also figure out Grant Williams and Malcolm Brogdon's futures with the franchise.

There's also the question of how aggressively Boston wants to pursue acquiring Damian Lillard. As previously explored, the most likely path to making that happen involves a three-team trade sending Brown to a franchise more confident in him re-signing after the season. That organization could then supply the Trail Blazers with a package of promising young players.

But even if the Celtics could add Lillard without having to part with Brown, it's fair to question whether those two, Jayson Tatum and Kristaps Porzingis, would mesh on the court to convert their individual abilities into a championship team.

Furthermore, according to Ramona Shelburne of ESPN, while Boston's expressed interest in striking a deal for the seven-time All-NBA guard, "this is not a team on the list, (and) this is not a city he would necessarily welcome going to right now, at least from what I understand."

In a previous appearance on NBA Today, Marc Spears of ESPN and Andscape shared he's heard Tatum is recruiting Lillard to join the Celtics. So, perhaps the four-time All-Star convinces the latter to embrace the chance to compete for titles alongside him in Boston.

However, Spears stated in an ESPN roundtable discussion about the NBA offseason he's told, "While Portland isn't happy with potential packages, there are over five teams interested in a potential multi-team trade that could get it done."

As the league descends upon Las Vegas for Summer League, akin to the NFL converging in Indianapolis for their draft combine, it could lead to the in-person conversations that produce a resolution to Lillard's trade request.

As Spears suggests, the most likely outcome remains the seven-time All-Star gets his wish and goes to Miami. But this author doubts he'd be a bad teammate on or off the court if wound up elsewhere, and the Trail Blazers must do what's best for them, or at least only go so far to accommodate their soon-to-be former face of the franchise.

But while it only takes one team to make an offer enticing enough for Portland to agree to it, history suggests Lillard will be taking his talents to South Beach.

Further Reading

The Latest on Celtics' Negotiations with Jaylen Brown

Mavericks Signing Matisse Thybulle to Offer Sheet, Potentially Eliminating a Grant Williams' Suitor

Marcus Smart Wants It Known There's No Beef Between Him and Jaylen Brown: 'We're Brothers'

Jayson Tatum Reportedly Recruiting Damian Lillard to Join Celtics

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

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

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'