John Henry, the principal owner of the Boston Red Sox, admitted Sept. 27 that whoever he hired as head of baseball operations would face a “challenging offseason.”

Henry finalized a contract Friday with Chaim Bloom, a 36-year-old Yale graduate. The Red Sox will introduce Bloom at a news conference at Fenway Park at 1:30 p.m. Monday.

This offseason should be one of the most challenging in the organization’s recent history. It will begin with Bloom deciding whether to re-sign J.D. Martinez if Martinez opts out of his contract’s remaining three years, $62.5 million. Martinez has five days following the World Series to inform the Red Sox about his decision.

Ownership’s goal is to keep the 2020 payroll under the $208 million Competitive Balance Tax threshold. That said, the 2020 payroll already is approximately $218 million before any offseason transactions.

Bloom likely must decide between keeping Martinez or Mookie Betts, the 2018 AL MVP who is eligible for free agency after the 2020 season and has expressed no interest in signing a contract extension. Betts strongly has indicated he intends to test free agency.

Sam Kennedy, the team president, said Sept. 30 it’s possible to keep the payroll under $208 million and still have both Betts and Martinez next season.

“There is a way but obviously it will be difficult given the nature of the agreements and the contracts that we have in place,” Kennedy said.

Betts likely will receive $30 million, or maybe more, in salary arbitration for 2020.

“We’ll have some conversations with him going forward,” said the Red Sox chairman, Tom Werner, on Sept. 27. “But obviously there will be a point where hopefully we can make a deal. Or we’ll decide at that point what is Plan B or Plan C? But we haven’t gotten to that point. And we’re very open to continuing the discussions with him.”

Bloom should set a hard deadline this offseason for completing a contract extension, then explore Betts’ trade market if the sides fail to negotiate a deal. Maybe Boston could secure a couple pitching prospects in return as they look to rebuild the farm system.

Bloom also must decide if he’d rather keep Martinez or Betts.

Martinez is 32 and has suffered back issues the past few years. Betts is 27, has no significant injury history, has established himself as a perennial MVP candidate and is a finalist for his fifth straight Gold Glove.

Betts obviously is the better player, but it comes down to more than who’s better.

Martinez has remained one of baseball’s elite hitters in his two years in Boston. He has 79 homers and a .985 OPS despite back issues. And he’ll cost less than Betts.

A lot less.

Martinez likely will opt out of his contract’s remaining three years, worth $62.5 million, to try and earn more money. He presumably will sign for around $100 to 120 million. Betts, meanwhile, likely is holding out for a contract somewhere between Bryce Harper’s 13 years, $330 million and Mike Trout’s 12 years, $430 million.

Do the Red Sox want the better player or the slugger who potentially could cost $200-300 million less?

Most longterm contracts don’t age well. We’ve seen it over and over.

Bloom also must add a fifth starter with Rick Porcello headed to free agency, as well as a reliever.

“We’re going to hopefully supplement our relief pitching,” Werner said.

Will he replace first basemen Mitch Moreland and Steve Pearce as well as super utility man Brock Holt with internal or external candidates?

Dustin Pedroia has appeared in nine games the past two years after major knee surgery. Bloom must figure out who will start at second base because he can’t rely on Pedroia to return.

The new boss must replace Martinez if Martinez leaves via free agency or Betts if Betts is traded.

All these potential additions must be made while trying to stay under the $208 million tax threshold.

Henry is entrusting this challenging offseason to Bloom, who cut payroll, operated on a low budget and traded top talent as Tampa Bay’s vice president of baseball operations from November 2016-2019.

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