The Red Sox could let Xander Bogaerts walk. David Ortiz, Jason Varitek, and Pedro Martinez have been there.

David Ortiz (right), pictured in 2015, has been in Xander Bogaerts's position.Barry Chin/Globe Staff

Pop quiz: Who was the last Red Sox cornerstone player to depart in free agency?

Mookie Betts, of course, was traded in the spring of 2020, nine months before he would have had a chance to test the open market. Jon Lester was shipped out in July 2014 as he neared the end of his contract, and both Manny Ramirez (2008) and Nomar Garciaparra (2004) were dealt at trade deadlines in their final seasons under contract.

As for those who did leave as free agents, Eduardo Rodriguez was a valuable contributor for the Sox but never a building block before his departure for the Tigers after 2021. The Red Sox made little effort to retain Jacoby Ellsbury (2013) or Jonathan Papelbon (2011) when they reached free agency. Neither Adrián Beltré nor Victor Martinez had been around for long enough to be considered a cornerstone player before they left after 2010.

Meanwhile, though the Red Sox let David Ortiz arrive at free agency twice (after the 2011 and 2012 seasons), they brought him back both times — once when he accepted their offer of salary arbitration, and then again just weeks into the start of free agency in 2012.

Jason Varitek reached free agency three separate times and re-upped each time.

Not since Pedro Martinez after the 2004 season and Johnny Damon after the 2005 campaign has a Red Sox cornerstone player reached free agency and, despite the efforts of the team to retain him, departed for another club.

With Xander Bogaerts eligible to opt out of the remaining three years and $60 million of his six-year, $120 million deal after the World Series, that history seems relevant.

What does the future hold for Xander Bogaerts?Jim Davis/Globe Staff

“I’m not going to lie to you, sometimes the Red Sox like to wait on certain things,” said Ortiz. “The longer you wait, the more it’s going to cost you, but they always were willing to pay. That’s a good thing. That gives hope for Bogey to come back.”

Of course, talks between the Sox and Ortiz were at times tense. Ortiz was open about feeling underpaid at different points in his career. When he finally reached free agency after the 2011 season, the Sox and their iconic slugger got into a staring contest, nearly going to salary arbitration prior to an 11th-hour settlement that extended his tenure in Boston for one year.

As the Sox looked to move forward from their embarrassing 2012 campaign with Ortiz again reaching free agency, it altered how they approached negotiations, and they quickly signed him to a two-year deal that set the stage for him to remain in Boston for the rest of his career.

“It was important that the organization stepped in and said, ‘Hey, you’re going to be here as long as you’re healthy. We don’t need to have these contract talks every year,’ ” said Ortiz. “I was in free agency for a minute [in 2012], but I never got my mind off of being a Red Sox. I had people approach me, but I didn’t want to have conversations with somebody else but the Red Sox.”

Like Bogaerts, Varitek was represented by Scott Boras. The catcher signed a three-year extension with the Sox prior to the 2001 season that bought out one of his free agent seasons, then, after arriving at free agency following the 2004 championship, he again hit the open market.

At times that winter, he thought his Red Sox tenure was over.

“That’s part of going into free agency. It might happen,” Varitek recalled. “And then very late in December, just before Christmas, it all came together. But it didn’t really look as though it was going to.”

Varitek received a four-year, $40 million deal that included a no-trade clause. He subsequently reached free agency twice (after the 2008 and 2010 seasons) before re-signing both times. Does he see any relevance to his own experience as Bogaerts nears the chance to opt out?

“They’re two different entities when you have a superstar in Bogey and you have myself, a very good major league player at my position but not a superstar,” said Varitek. “I had an underlying desire to make things work in this uniform first, while seeing the opportunity of what else is there — but to exhaust all alternatives here first.

“It wasn’t always easy for it to happen that way. Some chips had to fall in the right directions, both business-wise, want, need, and opportunity for that to happen. So I was very fortunate. That was part of my DNA that I wanted it to. But sometimes what you want isn’t always what this game offers.”

Jason Varitek (left) congratulates Pedro Martinez after a game in 1999. Both players have seen what it's like to negotiate with the Red Sox in free agency.The Boston Globe/Boston Globe

That was the case for Martinez, who said that when he arrived at free agency alongside Varitek after the 2004 World Series, he was willing to give the Red Sox a discount to return. At the time, Martinez was said to be seeking a four-year deal but remained open to returning for three.

The Sox eventually made a three-year offer in December, but by that point, talks had advanced with the Mets, who offered a fourth guaranteed year. Martinez suggested that, as much as the Sox paid lip service to a desire to bring him back, their deliberate approach to negotiations paved the way for his departure.

“They thought they were going to bring me back. The thing is, they did it a little too late,” Martinez recalled. “I wasn’t going to sit down and take a gamble waiting on the Red Sox to bring me back. I had secured what I wanted with a different team, which was the Mets at that point.

“And even though I [offered to] take a pay cut, they just didn’t come back to me on time. And I couldn’t take that chance to let go the best contract that I could probably get to wait for the Red Sox to kind of be sentimental and say, ‘Oh, we know Pedro loves it here. We’re going to bring him back.’

“No, it was the time to take care of business. I did that. I hope that Xander is not put in the same position that I was put in, having to wait, having all sorts of offers.”

After their tepid extension offer to Bogaerts in spring training (tacking on one year and $30 million to the original three years and $60 million), the Sox have publicly declared their intention to avoid dawdling. Chief baseball officer Chaim Bloom said in an end-of-season press conference that retaining Bogaerts is the team’s first priority of the offseason, and that they immediately would make an effort to keep him.

Whether that results in an extension remains to be seen. But at the least, the last two decades suggest that the departure of an iconic franchise player once he reaches free agency should not be taken as a foregone conclusion.