Yankees: Predicting which free agents they'll bring back in 2020

5 of 6

This offseason the Yankees will have some interesting decisions to make because a handful of key players from their current roster can become free agents. Which of them will be back in the Bronx for the 2020 season?

The playoffs are just six days away and the Yankees are one of the favorites to win their 28th championship in franchise history this October. They’re also in a great position to contend for multiple championships in the coming years if they can keep the majority of their current roster intact.

However, that might be difficult to do because as many as eight Yankees can enter free agency after the season ends. The odds of all of them returning for the 2020 season are likely slim, but for the sake of this list, I’m going to try and predict who will be resigned.

RP Cory Gearrin

Gearrin has only been a Yankee for a month after he was claimed off waivers from the Seattle Mariners on August 23rd. Gearrin has pitched a decent amount since coming to New York, but he hasn’t been, posting a 5.25 ERA in 16 games. The Yankees took a flyer on the 33-year-old right-hander hoping he could bolster their bullpen, but he likely won’t even make the playoff roster so I don’t expect to see him back with the club next season.

Prediction: Gearrin will not be re-signed

OF Cameron Maybin

Maybin has been excellent with the Yankees ever since they acquired him from the Indians on April 25th for cash considerations. Along with Mike Tauchman, he’s been a savior in the outfield filling in for Aaron Judge, Aaron Hicks, and Giancarlo Stanton after injuries sidelined each of them for extended periods of time throughout the year.

Offensively, Maybin has been an impact player in 80 games hitting .289 with 12 HR, 17 2B, 32 RBI, and a .502 SLG%. He’s also provided great defense at the corner outfield positions and has stolen nine bases. He’s been everything the Yankees could’ve hoped for and then some and he’ll continue to play a key role off the bench during the postseason. However, the Yankees are loaded with outfielders when everyone is healthy which is why I have a hard time seeing Maybin back in pinstripes next season.

Hicks, Stanton, Judge, and Tacuhman aren’t going anywhere and there’s a good chance Clint Frazier and Brett Gardner will be back in the fold as well. Maybin has been a joy to watch with the Yankees this year and his teammates are going to miss his hugs after they hit a home run, but he’s probably the odd man out given his contract status.

Prediction: Maybin signs elsewhere

Brett Gardner

Speaking of Brett Gardner it’s hard to imagine him leaving the Yankees this offseason after the career year he’s put together in 2019. Gardner re-signed with the Yankees very early into last offseason for a one-year, $7.5M deal and he’s been worth every penny. Coming into this season he wasn’t expected to play nearly as much as he has in year’s past but due to all the injuries in the outfield, he’s had to.

He’s played in 139 games so far and has set a career-high with 28 HR and 73 RBI. He’s done it batting all over the lineup and this season he hasn’t hit a wall at all in the second half as he has in recent years. He’s also played his usual gold glove defense in left field and in center with Aaron Hicks on the IL.

Off the field, he continues to be one of the top veteran leaders in the clubhouse and on the field he’s the heart and soul of this Yankee team. Entering the 2019 offseason I thought there was a chance he might sign elsewhere but this winter I don’t think there’s any doubt he’ll be back. The Yankees are the only team he’s ever played for and neither he or Brian Cashman wants to see that change. Gardy still has a lot left in the tank and until he shows otherwise I expect he’ll finish off his career in pinstripes.

Prediction: Gardner re-signs for another one-year deal

DETROIT, MI – SEPTEMBER 10: Edwin Encarnacion #30 of the New York Yankees (R) celebrates with Gary Sanchez #24 after hitting a two-run home run to tie the game against the Detroit Tigers at 10-10 during the seventh inning at Comerica Park on September 10, 2019 in Detroit, Michigan. (Photo by Duane Burleson/Getty Images) /

DH/1B Edwin Encarnacion

Encarnacion is hopeful to return to the lineup this weekend after suffering an oblique strain back on September 12th. I he can he’ll be back just in time to get a handful of at-bats under his belt before the postseason. Now whether he’ll be back with the club in 2020, that remains to be seen. The veteran slugger has a team option for $20M next season, but he also has a $5M buyout clause the Yankees can pay which would allow him to become a free agent.

Out of all the potential free agents on the roster, Encarnacion’s future in New York might be the toughest to predict. I think the Yankees would love to bring him back as their primary DH and part-time first baseman next season, but he’s probably not going to be their top priority when free agency begins. The focus will be on starting pitching and Aroldis Chapman if he becomes a free agent.

Based on his performance this season (34 HR, 86 RBI) Encarnacion is worth $20M for one more season, but the Yankees might not be willing to pay that high of a price when they already have guys like Stanton, Voit, and LeMahieu to take up the majority of the at-bats at first base and DH. That’s not even mentioning Miguel Andujar who could also figure into the mix if he changes positions.

Despite missing some time due to injury Encarnacion has been very productive for the Yankees hitting .249, with 13 HR and 37 RBI in just 44 games. He’ll be 37 next season and he also still has a lot left in the tank, but my guess is he won’t be back with the Yankees and they’ll invest their money ion starting pitching instead and guys like Gerrit Cole or Stephen Strasburg.

Prediction: The Yankees will pay the $5M buyout clause and Encarnacion will become a free agent.

RP Dellin Betances

Dellin Betances’ comeback from injury came to a heartbreaking end two weeks ago when he suffered a partially torn Achilles in his first big league appearance of the season. It was a crushing blow to the Yankees but an even bigger one to Dellin who was finally set to become a free agent after the season.

Fortunately, it doesn’t look like he will need surgery which bodes well for him being able to play next season once he’s all healed up. However, he won’t be cashing in this winter and sign a big contract like he was expected to coming into the season which is a shame. If he’d been healthy all season Betances surely would’ve been able to sign for a multi-year deal with a salary close to or above $10M but now he’ll be lucky to get any offers for more than a year or two.

That’s why I think the injury increases the likelihood he’ll be back with the Yankees because his value won’t be as high and he’ll be much more affordable. The Yankee bullpen is still stacked with dominant arms but they’d be happy to make room for Dellin if he’s willing to accept a short term deal for say, one year, with an option for a second. Given his current injury status I think he would take that deal and return to his hometown team and the only franchise he’s ever played for. After team president, Randy Levine basically trashed on Betances during their memorable arbitration case two years ago the Yankees owe it to him after all he’s done for the organization.

Prediction: Betances stays

C Austin Romine

Romine is the best backup catcher in baseball so it will be interesting to see if he signs with a team that will give him a starting job when he becomes a free agent for the first time this offseason. He’s earned that opportunity after backing up Gary Sanchez for the past four years.

SS Didi Gregorius

A couple of months ago I would’ve said there’s no way the Yankees would let Didi Gregorius walk as a free agent this offseason. Today, I’m not nearly as confident because of how much Didi has struggled offensively this season. After missing the first two months recovering from offseason TJ surgery Didi has only appeared in 80 games and he’s hitting .240 with 16 HR and 58 RBI. From a power standpoint that’s not bad, but the average isn’t Didi like at all and his OBP is team worse .279.

Didi himself has admitted that he hasn’t taken off yet and recently he went as far as to say “he’s sucked.” As a fan, I think he’s being way too hard on himself because his defense hasn’t hurt the team at all and with RISP he’s still been very clutch hitting .303. However, there’s no doubt it’s been a struggle for him at the plate, especially in September (.194 BA) with the playoffs right around the corner.

Coming off TJ surgery it’s not all that surprising to see Didi’s production take a dip, but it definitely could hurt his market value this offseason. Whether that makes it more or less likely for him to return to the Yankees remains to be seen but the good news for Didi is he’ll have a chance to make a strong final impression with a big postseason.

Didi has stepped up on the October stage before and it would surprise me at all if he gets hoit and does it again this year. That’s his primary focus right now and the rest will work itself out because despite taking a step back offensively this season he’s still going to garner plenty of interest as a free agent and make a lot of money.

It’s going to be a very tough decision for the Yankees because they could let Didi walk and spend some of the money they were going to pay him on an ace like Gerrit Cole. They already have another shortstop in Gleyber Torres who could shift over and replace him and DJ LeMahieu to take over for Gleyber as the starting second baseman. I think that’s a very real possibility but I also know that Didi wants to stay in New York and if he’s willing to agree to a slight hometown discount the Yankees would love to keep him here long term.

There’s really no way of predicting how this will play out until we see how Didi performs in the playoffs, but I have confidence he’s going to make a huge impact this October and the Yankees will realize how much they need him. He’s still their best left-handed power threat and a gold glove caliber defender and there isn’t a player on the roster who’s more beloved by the fanbase. That means a lot and I hope that enough to convince management to bring him back.

Prediction: Didi re-signs on a long term deal

NEW YORK, NEW YORK – JUNE 01: Aroldis Chapman #54 of the New York Yankees celebrates after defeating the Boston Red Sox 5-3 at Yankee Stadium on June 01, 2019 in New York City. (Photo by Mike Stobe/Getty Images) /

CL Aroldis Chapman

Chapman is enjoying another outstanding season as the Yankees closer and this offseason he’ll have a chance to opt-out of his contract and become a free agent. He has absolutely lived up to the five-year, $86M deal he signed to return to New York before the 2017 season so the odds are he’ll opt-out and cash in on another big deal.

If he wants more years of financial stability he’d be crazy not to opt-out but that doesn’t mean he’s not going to return to the Yankees. He’ll have plenty of teams interested in signing him but Brian Cashman and company are probably going to do everything in their power to make sure they bring him back.

If he doesn’t opt out Chapman is set to make $17.2M in each of the next two seasons which is a very high AAV for a reliever. He might not be able to earn a salary that high in free agency, but he should be able to get a deal for more than two years with an AAV of a couple of million dollars less. Something along the lines of a four-year, $60m makes sense for Chapman which is a figure I don’t think the Yankees would hesitate to offer him.

Next. Ranking CC Sabathia's top five moments as a Yankee. dark

Again, I’d be shocked if Chapman doesn’t opt-out after the past couple of years he’s put together, but I’d be even more shocked if he isn’t back with the Yankees next season. He’s far too important to their team and they won’t let him slip away and sign with another club.

Prediction: Chapman opts-out and re-signs with the Yankees

Home / Yankees News