Celtics still talking extension with Jaylen Brown as deadline looms

With the rookie extension deadline looming on Monday at 5 p.m., the Celtics are still in the midst of negotiations with Jaylen Brown about a potential new deal. Brown's newly hired agent Jason Glushon was at the Auerbach Center at the conclusion of practice on Monday as the 23-year-old swingman worked out on the floor after the session. Danny Ainge and Mike Zarren were also in the building, setting the stage for a final negotiation push ahead of the Monday deadline. If Brown does not reach an extension now, he will hit the restricted free agent market on July 1st.

The Celtics have not reached a rookie extension with a player since 2009 (Rajon Rondo) but plenty of movement on the extension front this weekend has helped to set more of a market for both sides to work off of. The Raptors reached a four-year max extension with Pascal Siakam on Saturday, a number that probably didn't help both sides find common ground with their numbers. Things may have changed on that front on Monday morning as Sacramento reached a four-year, $94-million deal with shooting guard Buddy Hield that could get pushed to as much as $106 million based on incentives.

Those deals now put the total at five players who have reached rookie extensions since the summer.

Ben Simmons: Five years, $168 million
Jamal Murray: Five years, $168 million
Pascal Siakam: Four years, $130 million
Buddy Hield: Four years, $94 million
Caris LaVert: Three years, $53 million

So where exactly in that range puts Brown ahead of the deadline?

As Ryan Bernardoni laid out earlier this month, there appears to be some healthy middle ground at this point for both sides for negotiations the four years, $90-100 million range. Hield is a far different player compared to Brown due to his offensive scoring ability but Brown's defensive potential is miles ahead of the Kings' guard and Brown is also a couple of years younger to boot.

The question that Brown and his agent now have to wait is how much risk are they willing to swallow heading into next summer. Brown may feel like he's on the same par as Murray when it comes to his ability but he's going to need to find a team willing to give him that type of money next summer with a breakout year if Boston isn't willing to do it. With only four teams projected to have more than $20 million in salary cap room next summer at this point, it could be a tougher market for the 6-foot-7 swingman that he envisioned.

League sources tell BostonSportsJournal.com that there is more drama this time around on deadline day than any recent years. Boston never got very close with Terry Rozier or Marcus Smart in the past two seasons but there is an incentive from both sides to get things done now for an ideal number. The Celtics won't have cap room next summer whether or not an extension gets done now and having Brown locked in as a trade chip or building block for the long term is preferable for Boston's front office at the right price.

The guess here is the two sides fall short but the uncertainty surrounding the market next summer may get Brown's camp to blink. Stay tuned.