Three thoughts after Celtics splurge to extend Jrue Holiday

Three thoughts after Celtics splurge to extend Jrue Holiday originally appeared on NBC Sports Boston

A handful of immediate thoughts after the Boston Celtics and Jrue Holiday agreed to a four-year, $135 million extension:

1. Security for both sides

After paying a hefty price to acquire Holiday on the eve of training camp for the 2023-24 season, all with no guarantee that he’d stick around beyond the current season, the Celtics splurged again Wednesday to ensure he’ll be here for as long as the team is willing to pay for this title-contending core.

Holiday gets a big payday in advance of his 34th birthday and can dive into both the 2024 playoffs and 2024 Olympics with his long-term future secure. The Celtics don’t have to worry about Holiday’s status entering a summer in which Jayson Tatum’s supermax extension becomes the top priority.

2. Brad Stevens loves extensions

In the two-plus seasons since his surprising elevation to president of basketball operations in 2021, Stevens has embraced extensions at every opportunity.

Add Holiday to a list that also includes Marcus Smart, Robert Williams III, Josh Richardson, Al Horford, Kristaps Porzingis, Jaylen Brown, and Payton Pritchard. The investments in Smart and Williams III helped Stevens craft the moves to acquire Porzingis and Holiday. Richardson went out in the deal to acquire Derrick White.

Stevens appears to see extensions as investments that allow his players to keep their focus on the goal at hand while also giving the team long-term ability to shape its roster using those new deals. Holiday’s future could have hovered over the team’s postseason run, and while it creates some long-term concerns with a ballooning payroll, the team seems content to cross that bridge further down the road.

3. Flexibility next year, difficult decisions after

Holiday was on the books at $37.4 million next season with a potential cap hit of $39.4 million with incentives. That number will dip closer to $30 million, affording the team some additional flexibility as it tries to navigate the second apron in a restrictive new collective bargaining agreement.

Boston’s roster is solid enough that maneuvering above the second apron isn’t a paralyzing concern. It’s not ideal but it’s manageable if the team is deep enough to compete for titles.

It’s the luxury tax bills and repeater penalties when supermax deals for Brown and Tatum hit the books that will be tougher to navigate.

Boston’s projected payroll for the 2024-25 season is closing in on $200 million, and that’s before dealing with impending free agents like Luke Kornet and midseason acquisition Xavier Tillman. Holiday’s new deal does give the Celtics potential avenues to dip below the projected second apron while maintaining the core of a team that posted the best record in basketball this season.

Things get trickier in the summer of 2025-26 as repeater penalties kick in. Both Tatum and Brown would be on supermax deals at that point, while Holiday and Porzingis would be earning $30+ million apiece. And that’s before any new deal to retain extension-eligible White. That’s a potential $200 million starting five before even filling out the depth pieces (with Payton Pritchard and Jordan Walsh the only players currently under contract for that season).

All future decisions get a whole lot easier if the Celtics are able to obtain Banner 18 this summer. They can splurge to keep the band together and hunt titles, or pivot with the goodwill that winning a title affords.

But, for the moment, there’s one less distraction in this year’s quest for Banner 18. Holiday has been rewarded for the sacrifices he’s endured joining a loaded roster. And the Celtics might ultimately be rewarded with a banner for the investments they’ve made to this core.