Deadlines to watch for Stras, J.D., Chapman

With no more than two games remaining in the 2019 season, the rest of Major League Baseball is prepping for what could be an eventful offseason.

Free agency doesn’t officially begin until 5 p.m. ET on the fifth day after the conclusion of the World Series, which also happens to be the deadline for clubs to extend qualifying offers to eligible free agents. And while all 30 teams know some of the players who will be hitting the open market, some pretty big names could be added to that list during the five days between the end of the Fall Classic and the start of the free-agent signing period.

Stephen Strasburg, J.D. Martinez, and Aroldis Chapman are the three most prominent players who could opt out of their contracts later this week. Of course, each player’s contract has its own specific opt-out deadline, which we outline below. None of these three players has received a qualifying offer before, which means they are all eligible if they opt out and would almost certainly receive a QO. As a result, their current clubs would receive Draft-pick compensation if they sign elsewhere, and their new team would have to forfeit a pick.

(Note: There are other players with opt-outs, notably Yu Darvish, Kenley Jansen, Jake Arrieta, Elvis Andrus and Jason Heyward, but they are expected to decline them and remain on their current contracts.)

Stephen Strasburg, RHP, Nationals

Remaining contract terms: Four years, $100 million

Opt-out deadline: 3 days after the World Series

It is widely assumed that Strasburg wants to stay in Washington, so he and agent Scott Boras could try to leverage the opt-out into an extension of his current deal. Both CC Sabathia and Clayton Kershaw took this approach and earned millions more without having to venture into the unknowns of free agency.

But Boras relishes the opportunity to take his high-profile clients to the open market, and given Strasburg’s superb regular season (18-6, 3.32 ERA, National League-best 209 innings pitched) and spectacular postseason (4-0, 1.93 ERA through five games heading into Tuesday’s Game 6 in Houston), the timing couldn’t be better.

• Here are 5 potential suitors for Strasburg

The Nationals would certainly extend a qualifying offer if he opts out, guaranteeing them Draft-pick compensation if he leaves for another club. The QO wouldn’t likely have much impact on Strasburg in free agency, as top starting pitchers are still among the game’s most precious commodities.

Strasburg is 31, so it’s unclear whether a team would give him a six-year contract.

“On the open market, I don’t think teams would go beyond five years,” one AL executive said. “He’s had one Tommy John surgery already.”

Multiple executives believe Strasburg and the Nationals will come to terms on a restructured deal before the opt-out date, though that means it must happen within 72 hours of the conclusion of the World Series -- and in case you’ve forgotten, Washington is one of the participants. Bottom line: Anthony Rendon, Strasburg’s teammate, is a free agent this winter, and it’s hard to imagine the club risking the loss of both Strasburg and Rendon after the season it has had.

Aroldis Chapman, LHP, Yankees

Remaining contract terms: Two years, $30 million

Opt-out deadline: 3 days after the World Series

This year’s Mariano Rivera Award winner as the best reliever in the American League, Chapman seems like a lock to opt out of the final two years of his contract with the Yankees.

The question is: Should he?

Chapman earned $56 million over the past three seasons ($15 million per year, plus an $11 million signing bonus that was paid out between 2017-19), part of the five-year, $86 million pact he signed with the Yankees in December 2016.

The obvious comparison here is Craig Kimbrel, who was hampered by a qualifying offer last offseason, as teams were seemingly hesitant to give up big money and Draft-pick compensation to a closer with declining strikeout and walk numbers. Kimbrel -- who ended up struggling with the Cubs -- waited until June to sign his three-year, $43 million deal with Chicago, which will pay him $16 million in each of the next two seasons.

Chapman, like Kimbrel, is 31 and has been an All-Star in each of the past two years, posting a 2.33 ERA in 115 appearances while striking out 14.8 batters per nine innings. He might not throw 102 mph as consistently as he once did, but he still lives in the upper-90s with an improved slider, and he can reach back for triple digits when he needs it.

“Chapman will get more [than Kimbrel],” an AL executive said. “And he won’t have to wait.”

The Yankees could bring Chapman back on a longer deal -- the executive predicted a four-year, $60 million contract, which would double what he’s currently owed -- though there would be other suitors as well. Should the Yanks lose Chapman, they would get a Draft pick when he signs elsewhere, and Zack Britton could step into the closer role for New York, which would likely look to bolster the bullpen with another acquisition or two.

J.D. Martinez, OF/DH, Red Sox

Remaining contract terms: Three years, $62.5 million

Opt-out deadline: 5 days after the World Series

Unlike Strasburg and Chapman, Martinez has five days after the World Series to make his decision, giving him and his agent -- he’s also repped by Boras -- an additional 48 hours to monitor the market as teams choose whether to exercise their own options on a number of players.

Martinez’s two years in Boston have been extraordinarily productive; he’s slashed .317/.392/.593, averaging 40 home runs and 118 RBIs. The problem Martinez may face as a free agent is the same one he did two years ago: He’s generally viewed as a DH, limiting his market to American League teams.

Unlike two years ago, Martinez is now 32, so while he might be able to score a deal longer than the three years he has left on the five-year, $110 million contract he signed with Boston in February 2018, that deal was front-loaded -- his annual salary will dip from $23.75 million to $19.375 million beginning in '21 -- and presumably structured in that fashion to maximize earnings prior to an opt-out.

• 5 fits if Martinez leaves Boston

But will he opt out? Internally, the Red Sox are split on that question, with some in the front office believing Boras will encourage Martinez to trigger the escape clause. Others in Boston think Martinez will stay, knowing he can opt out of the deal next season before his annual salary drops by more than $4 million per year.

Should Martinez stay, it could increase the odds that new chief baseball officer Chaim Bloom will have to trade Mookie Betts in an effort to get the payroll below the $208 million luxury-tax threshold. Replacing Martinez’s bat won’t be easy if he leaves, though keeping Betts in Boston for one more year -- or at least until the summer, when the Red Sox will have a better idea of their postseason chances -- is an attractive alternative.