Boston Celtics president of basketball operations Brad Stevens has had to make some tough decisions since replacing Danny Ainge in 2021. This upcoming offseason, however, is shaping up to be his most challenging yet.
Restrictive second-apron penalties will force Stevens and the C’s to make noteworthy roster changes this summer. Boston, which is currently $20 million over the threshold, must decide whether to attempt to “thread the needle” with tweaks to its championship core or undergo a full reboot.
Will Stevens channel his inner “Trader Danny”? Yahoo Sports’ NBA insider Kevin O’Connor made the case for Stevens to maximize his players’ trade value this offseason.
“I think back to Danny Ainge,” O’Connor told co-hosts Drew Carter and Chris Forsberg on NBC Sports Boston’s The OffC’season special. “Danny Ainge, what did he do when he traded Kevin Garnett and Paul Pierce to the Brooklyn Nets? Two things: A, he traded them before they fell off a cliff. Before they aged out and before they were near retirement. And B, he took advantage of a completely desperate franchise in the Brooklyn Nets. That’s why they got Jayson Tatum, that’s why they got Jaylen Brown, that’s why they had 10 straight years of making the playoffs and why they won a Finals.”
Of course, Pierce was 35 and past his prime when he and the Celtics parted ways. Kevin Garnett was 36 and his best days were well behind him.
Boston’s most valuable trade chips, Jaylen Brown and Derrick White, are 29 and 31, respectively. Both are in the prime of their careers.
Trading oft-injured 30-year-old big man Kristaps Porzingis or 35-year-old guard Jrue Holiday seems more realistic, though O’Connor wouldn’t take anything off the table if another general manager calls Stevens with an enticing offer.
“For Stevens, he needs to find the most desperate team,” O’Connor added. “Whether that means Brown or White, or whether it means (Kristaps) Porzingis as an expiring salary, or whether it means Jrue Holiday as the final piece for the Dallas Mavericks and Nico Harrison’s vision. Whatever it is, finding the most desperate team to get the best value back based off of how you perceive your own player.
“That could be a lot of pain. It might mean trading Derrick White. But if the Warriors are going to give you a Mikal Bridges type of deal like four, five first-round picks, how do you say no? You can’t say no.”
Holiday has already been connected to the Mavericks in trade rumors, and the Warriors have reportedly “looked into” White as a potential option. O’Connor notes White especially as someone who could bring back a massive haul for the Celtics.
No matter what direction Stevens chooses, all signs point toward an uncomfortable offseason in Boston. The championship window may not be closed, but the window to win it all again with the 2024 core almost certainly has.
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