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The path to the Celtics acquiring Damian Lillard is complicated. An offer centered around a package of picks, including multiple first-round pick swaps, and Robert Williams, with or without Derrick White, is beatable.

Boston figures to remain in contention, denting the value of that draft capital; Williams comes with durability concerns, and while White's on one of the most valuable contracts in the NBA at a time when the transition to the new and more punitive collective bargaining agreement makes that even more important, he's 29.

If the Trail Blazers decide to embrace a youth movement around Shaedon Sharpe and Scoot Henderson, those players don't fit their timeline. Their other option is getting an All-Star caliber player in exchange for their current face of the franchise.

Even if the Celtics were willing to trade Brown to acquire Lillard, there would be no incentive for the former not to play out his contract, meaning Portland would either gamble it can convince him why it's worth sticking around or, even less likely, secure a commitment from the All-NBA wing it's willing to bank on before acquiring him.

The Trail Blazers would probably prefer more certainty about what they're getting back for the seven-time All-Star. That could lead to a three-team deal, where Brown goes elsewhere, perhaps the Rockets, reuniting with Ime Udoka, and a package of young players go from Houston to Portland.

But Lillard's a six-foot-two guard about to turn 32 and a defensive liability. Conversely, Brown and Jayson Tatum have guided Boston to the Eastern Conference Finals in four of their first six years together, including coming within two wins of Banner 18.

The older half of that All-NBA tandem is 26, just entering his prime. The latter, 25, isn't even there yet.

And according to ESPN's Brian Windhorst, appearing on SportsCenter, the expectation is the Celtics see if they can lead the franchise to a championship for at least one more season.

With Brown eligible to sign a five-year, $295 million veteran supermax extension, Windhorst labeled it a 'very important, fragile deal,' he expects it to get done. If that happens, the two-time All-Star isn't trade-eligible for a year.

Jared Weiss of The Athletic reports Boston wants to sort out other matters, such as figuring out Grant Williams' future, before getting Brown's deal done.

There's also a need to hash out the incentives in the latter's extension, whether it includes option years and if he's willing to sign for less than 35 percent of the salary cap.

No other team can offer Brown more than 30 percent of the cap. However, not only does he have every right to ask for his maximum potential earnings, he left money on the table in his last extension and is a vice president of the National Basketball Players Association.

But if he'll sign for less than 35 percent of the salary cap, it'll make it easier for the Celtics to build around him and Tatum when both of their extensions come on their books in 2025-26.

Otherwise, the franchise may decide two players accounting for roughly 70 percent of its cap space is untenable, resulting in Boston breaking up one of the NBA's top tandems, if it hasn't already done so.

Further Reading

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'