How the Portland Trail Blazers, Chicago Bulls, and Boston Celtics all benefit from this trade
Portland Trail Blazers
In this deal, the Portland Trail Blazers land a legitimate second option for Damian Lillard. Not only does Jaylen Brown provide a consistent scoring threat, but he also bumps Jerami Grant down into a more natural tertiary role and gives the Blazers perhaps the best two-way wing the Blazers have had during the Dame era.
While landing Brown would cost them a rising star in Anfernee Simons and two (or three) first-round picks, Portland has a natural successor for Ant already in place with Shaedon Sharpe, and keeping the third-overall pick potentially gives them a brighter future post-Dame than keeping those two or three selections down the road.
A top eight consisting of Dame, Sharpe, Brown, Grant, Jusuf Nurkic, Scoot Henderson!, Matisse Thybulle, and whoever they sign using their midlevel exception this summer gives them their best shot at a title since Lillard came to Portland.
Chicago Bulls
With Portland’s pick being lottery protected, it’s hard to envision the Chicago Bulls getting better value than this package by waiting for that selection to eventually convey. Rather than standing by and hoping that the Trail Blazers give them a pick better than 23 at some point in time, Chicago can upgrade their roster now and better assess the direction of their team with a concrete asset in hand.
Nassir Little gives the Bulls a rotation-ready forward with elite athleticism and two-way potential. Coupled with the 23rd overall pick in a deep draft, Chicago can choose to either build toward the future or try to return to the postseason with this move.
Boston Celtics
For the Boston Celtics, this deal is reliant on a couple of extraneous factors. Firstly, it would depend on Jaylen Brown’s feelings about the team. While he’s been rumored to be unhappy in Boston, that gossip has been passed around for several years now, and the Celtics do have the ability to give him a contract extension that would make him one of the highest-paid players in the entire league.
Secondly, it also matters how they feel about Anfernee Simons. It’s clear that Ant is a legitimate three-level scorer in this league, and at just 23 years old, has tons of room to grow and improve his game further. Simons’s ability to stretch the floor and create his own offense from nearly every spot on the court would take immense pressure off of Jayson Tatum’s shoulders, but it would be a significant downgrade on defense from Brown. That being said, with Marcus Smart and Derrick White on board, the C’s have no shortage of defenders ready to pick up the slack and fill in seamlessly next to Simons in the backcourt.
Lastly, if Jaylen Brown were to be officially put on the trading block, there’s a chance that another desperate team could trump Portland’s offer. While the Trail Blazers have plenty to give, there’s no telling what organizations like the Oklahoma City Thunder or New Orleans Pelicans would be willing to do, considering they’re both armed to the teeth with future first-round picks.
Ultimately, though, this deal keeps the Boston Celtics in contention, with Simons being arguably a better fit on offense alongside Tatum and the rest of the Cs than Brown, while also giving them plenty of options to build with moving forward. Getting younger, and possibly better, while tacking on an additional two or three first-round picks certainly wouldn’t be a bad route to take.