Celtics ‘Cleanly Get’ Under Second Apron With $304 Million Star Trade Proposal

With the Boston Celtics staring at a $500 million payroll and the roster-building restrictions of the dreaded second apron following Jayson Tatum‘s Achilles injury, which will keep him out for next season, will they entertain thoughts of trading Jaylen Brown?

That’s the question Yahoo Sports’ Kevin O’Connor asked on the latest episode of his podcast “The Kevin O’Connor Show” as the Celtics are increasingly likely to enter a gap year with Tatum’s injury.

Brown, locked in a five-year, $304 million deal, currently holds the best value among the Celtics holdovers from their 2024 championship roster. O’Connor believes Brown is the Celtics’ cleanest path to get under the second apron and get a haul of return, resetting their finances to have more flexibility when Tatum returns after next season.

Jrue Holiday will turn 35 in June and has three years remaining on a four-year, $134 million deal, including a $37.2 million player option in 2027-28. He’s coming off the worst season of his career since his rookie year offensively. The 29-year-old Kristap Porzingis, a prime trade candidate, has little value as an expiring $30.7 million contract after his playoff dud due to a mysterious illness and his lengthy injury history.

Derrick White will turn 31 in July and is locked to a four-year, $118 million pact that will start kicking in next season. He’s the Celtics’ next best trade chip after Brown.

A Blockbuster Trade to Get Boston Under Second Apron

Milwaukee Bucks star Giannis Antetokounmpo is the prize catch of this offseason, if he demands a trade.

Teams will line up to get him.

But only one team would get him. Brown as a consolation prize isn’t a bad idea, O’Connor suggested.

“If a team misses out on Giannis, could they pivot to Jaylen Brown and could that team be the Houston Rockets?” O’Connor wondered. “Could you see Ime Udoka, the head coach of Houston, reunite with Jaylen Brown with some type of offer like Fred VanVleet, the No. 10 pick this year and some number of future first-round picks?

“Van Vleet has a team option that can be declined if this deal were to happen before July 1st. The Celtics could cleanly get under the second apron by declining that option. It would give them immense flexibility, tons of future draft capital and without Jaylen Brown, you get to see what Derrick White could do, what Payton Pritchard could do with a ton more touches next season. You get to see what guys like Baylor Scheierman and Jordan Walsh — these young guys on their rookie-scale contracts — can offer.

“There’d be less pressure to move off Jrue Holiday or Kristaps Porzingis for low returns.”

Jaylen Brown’s Peak Value

Brown is a franchise pillar for the Celtics. He was their best player in their championship run last year, winning the Conference Finals MVP and the NBA Finals MVP awards.

“He has been awesome for Boston,” O’Connor said of Brown. “He’s been a great player, a great co-star next to Jayson Tatum for years, but he’s going to be 29 next season. He’s going to make $53 million and then $57 million and then $61 million and then $65 million.

“By that time, he’s in his mid-30s. This might be his peak value for a team that whiffs on Giannis and decides to let’s go to somebody else.”

Trading him would certainly draw backlash from Celtics fans akin to Dallas Mavericks fans when Luka Doncic was traded. But if the Celtics receive a godfather offer for him, it behooves them to at least consider it.