Does an extension for Gordon Hayward make sense for Celtics?

(Maddie Meyer/Getty Images)

The offseason is full of important questions for the Celtics but the biggest one begins with Gordon Hayward’s future in Green. The 30-year-old will have until a couple of days before free agency begins (no date is set yet, but likely in late November or December) to make a decision on his $34.1 million player option for the 2020-21 season.

There’s no chance that Hayward opts out of that contract unless he has a new deal waiting for him. Unlike Al Horford's surprise market last offseason, there isn’t a lot of open cap room waiting for Hayward in free agency this fall, particularly among contending teams. Only six teams are expected to have over $25 million in cap room this fall and just one of those is a playoff team (Miami) who has several of their own free agents they probably want to retain first. With a lot of teams facing a financial crunch in the wake of a pandemic, it’s hard to envision any squad that will be eager to throw enough money at Hayward on a long-term deal to convince him to walk away from $34 million next season in Boston.

The prospect of an extension with the Celtics could be on the table before Hayward opts in and is certainly something both sides will have an incentive to negotiate if important common ground can be found.

Boston’s perspective

The team is in win-now mode and will also be entering luxury tax territory next season in all likelihood, depending on where the NBA sets the salary cap and luxury tax threshold this fall. Reducing a $34 million salary cap hit for Hayward to something in the $20-30 million range would significantly decrease the C’s tax bill for the 2020-21 season, where they will have to be paying at least a $1.50 penalty for every dollar they spend over the projected $139 million tax line (subject to change).

Doing the math on those estimated tax figures is where things get interesting for Boston’s offseason spending options. Let’s say Hayward signs an extension that brings down his salary to $25 million for next season. If the Celtics were over the tax by five million if Hayward had opted into his $34-million salary, the team would save $9 million on his salary for next year with an extension in its place as well as an additional $7.5 million in tax penalties to bring total savings for $16.5 million with the move. That’s money ownership could pump directly back into the payroll next year to increase the C’s chances with free-agent signings.

The flip side of that scenario though is the length of any extension, something that could be a point of contention for Hayward and the Celtics. If Hayward is going to opt out of $34 million for a 30 percent salary decrease next year, he’s going to want some additional security tacked on to any deal to make sure he makes that money back and plenty more at the tail end of a new deal.

Paying Hayward big money beyond next season is where things get dicey for the Celtics payroll and cap situation though. Here’s a look at the team’s major financial commitments for the 2021-22 season with the assumption that Jayson Tatum signs a max contract extension this offseason.

2021-22 Celtics estimated salary commitments

Kemba Walker: $36 million
Jayson Tatum: $31.25 million (conservative estimate at 25 percent max)
Jaylen Brown: $24.8 million
Marcus Smart: $14.3 million

Four players: $106.9 million

Now, let’s say that Hayward’s agent is looking for a three-year extension worth $25 million per year if he’s going to opt out of his player option this season. That means the Celtics will have nearly $132 million committed to just five players for the 2021-22 season, a gigantic chunk of their payroll that will likely send the Celtics deep into the luxury tax if they want to field a competitive contender with their 15-man roster.

Cheap rookie contracts could help the Celtics fill that gap and keep the C’s salary numbers at a