The one team that has come up the most in the Jaylen Brown sweepstakes has been the Portland Trail Blazers. The Boston Celtics apparently don't have much leverage in a Brown trade, as it feels as though their divorce is inevitable. What's fascinating, though, is that Boston would have enough leverage on Portland that they could get the most possible value for Brown out of them.
Why's that, you may ask? Because the clock is ticking on Damian Lillard and Jrue Holiday, two of their most important players. Sending Brown to them forms a quartet of him, Dame, Jrue, and Deni Avdija. That would create one of the NBA's most formidable quartets for sure, but there's no telling how much juice Lillard and Holiday have left in their mid-to-late 30s.
After bringing in those two last year, Portland has signaled that they want to be on the same level as Oklahoma City and San Antonio ASAP. Those two help a lot with their aspirations, but it's fair to say that they are not enough. Getting their hands on Brown would change the equation for the better.
Because their ceiling would get that much higher, and it would give them maybe their best chance at toppling the best in the West, they would pull the trigger on a deal to get Brown.
But it's for that same reason that Boston should extrapolate every bit of value they can from Portland.
Celtics can use Trail Blazers' limited time against them
The Trail Blazers wouldn't offer Lillard, Holiday, or Avdija in a deal for Brown, and that should be fine for Boston. However, everything else should be on the table from Portland's end, as they can't let this opportunity slip through their fingers with the limited timeframe.
With that out in the open, Boston should ask for all the available picks, Donovan Clingan, Scoot Henderson, Toumani Camara, Shaedon Sharpe. These are all players who could be of good use for the Celtics. Would the Trail Blazers be okay with parting with all of those guys? Of course not, but the limited window they have may force them into trading most of them (emphasis on Clingan).
Oh, and of course, Milwaukee's pick swaps along with the pick Boston sent them in the original Holiday trade.
Even though Brown is the hottest topic on the rumor mill these days, the Celtics still have him on their payroll for the next three years. They can feasibly keep him instead of selling him for pennies on the dollar.
Even if that's not their plan, they can easily tell the Trail Blazers to have fun wasting what's left of Lillard's and Holiday's primes while they're left scrambling. Portland may not be willing to play ball, but the age of two of their most important players may force them to anyway.
And if they do, Boston is in great position to take great advantage of a situation not many think they can. This isn't a foregone conclusion, but it's definitely something to keep in mind.
