NBA Rumors: Jaylen Brown, Celtics Eye $295M Supermax Contract in 2023 Free Agency

The Boston Celtics and Jaylen Brown are reportedly optimistic they will be able to reach a five-year contract extension worth up to $295 million this offseason.

"The sides are talking. This is obviously a very important, fragile deal. I know there's interest on both sides to get something done, and I would expect it to head in that direction," Windhorst said Monday on SportsCenter. " ... I think it'll get done, but he's eligible up to 35 percent of the salary cap, but he doesn't have to get that. The Celtics can negotiate on that. They can negotiate on the player option. They can negotiate on several things. It's not as simple as saying, 'Jaylen, here's your contract. Sign it or not.' There's aspects within the deal you gotta negotiate."

Brown became eligible for a contract extension worth up to 35 percent of the salary cap by making an All-NBA team last season. He averaged 26.6 points, 6.9 rebounds and 3.5 assists on his way to earning All-NBA second-team honors.

Under the previous collective bargaining agreement, it likely would have been a no-brainer for the Celtics to offer Brown the full 35 percent max. Boston is a mortal lock to be a luxury tax team for most of the Brown-Jayson Tatum era if the franchise wants to compete, and the franchise sent a signal cost is no concern when it signed Kristaps Porzingis to a two-year, $60 million extension after acquiring him from the Washington Wizards.

That said, it's likely the Celtics—and all NBA teams—want to avoid the dreaded second luxury tax apron introduced in the new CBA. The second apron, which is currently set at $17.5 million above the tax apron, restricts teams from using the taxpayer midlevel exception, prevents them from using cash in trade purposes and freezes their first-round pick seven years in the future so it cannot be moved.

Even more restrictive penalties—highlighted by the "frozen" draft pick being moved to the end of the first round—come into play if a team repeatedly goes over the second apron.

This second apron is likely as close to a hard cap as the NBA will ever get and will lead to teams dumping salaries, allowing incumbent free agents to talk and generally being stingier about doling out massive contracts. Players like Brown—stars who are a step or two down from true foundational status—may see their teams try to squeeze out a few million dollars over the course of long-term contracts to give themselves more breathing room.

With Jayson Tatum due his own $300-plus million extension a year from now, Boston is looking at $600 million in guarantees without even thinking about the rest of the roster. That could lead to the Celtics asking Brown to take a slight cut on his full max extension to help roster maneuverability.