Yankees scenarios for handling Didi Gregorius and 7 other pending free agents

GM Brian Cashman has some tough decisions to make

10/31/2019, 12:30 PM
Dellin Betances/Didi Gregorius/Brett Gardnerundefined
Dellin Betances/Didi Gregorius/Brett Gardnerundefined

Scott Thompson, SNY.tv | Twitter |

With the World Series over (unfortunately without the Yankees starring in it), the hot stove season -- free agency, trades, and all the intrigue -- is officially here.

For the Bombers, they have eight players potentially set to hit free agency. And there's a strong chance that all of them will be playing for new teams in 2020.

The Yankees have a few top players who could hit the market, like Aroldis Chapman, Didi Gregorius, Dellin Betances, and Brett Gardner. So what should the Yanks do? Who should they bring back? 

Aroldis Chapman

Chapman can opt out of the final two years of the five-year, $86 million deal he signed with the Yanks back in 2017. If he does so, he's leaving $30 million on the table to test the free agent waters. 

And he could very well do that after earning the American League Reliever of the Year title for the season. However, Chapman is going to be 32 next season and has seen declines in that high-velocity fastball. With the Yankees, he has learned to be more deceptive, using his slider more to fool hitters. 

If he thinks it is worth the opt-out, the Yankees should go after him as he has been the team's closer with effectiveness for years now. But it will come down to if Chapman's agent believes his price would match that $30 million he's set to receive if he decides to opt in to the final two years. 

Didi Gregorius

This one is the trickiest for the Yankees. Gregorius is hitting the free agent market for the first time, but the Yankees are allowed to extend him a qualifying offer if they wish to do so. 

However, is Gregorius worth the $17.8 million that he would receive if GM Brian Cashman chooses to use the qualifying offer and he accepts? 

He has been a leader on and off the field after taking over for Derek Jeter at shortstop back in 2015. He has been a solid glove and has come through in clutch moments for the Yankees. But, after returning from Tommy John surgery, Gregorius had a modest season at the plate with a .238/.276/.441 slash line with 16 homers and 61 RBI over 82 games. There is also the prospect of Gleyber Torres being able to shift to shortstop to allow DJ LeMahieu an everyday spot at second base. 

The decision on Gregorius will be Cashman's hardest one to make this offseason. 

Dellin Betances

It was a sad sight to see Betances hit the IL once again just after a great return at the end of the season. A torn Achilles was his latest injury after suffering multiple ailments throughout the season. 

Betances' injury couldn't come at a worse time as he is no longer arbitration eligible, and hits the free agent market. With the Yankees bullpen already stacked, Cashman could let Betances go as he may not be worth the price tag. He hasn't been able to stay in the bullpen despite how effective he is when healthy. 

Brett Gardner

Like Gregorius, Gardner's leadership was critical for this year's Yankees -- if not more considering he's the longest-tenured player in pinstripes. Whether or not he'll continue to be that guy is to be seen. 

What helps Gardner's cause is the fact that Aaron Hicks will be out 8-10 months with Tommy John surgery recovery. Bringing Gardner back on a similar one-year deal like the Yanks did a season ago would make sense. Mike Tauchman is another option to fill in at center field, but after Gardner set career highs in homers and RBI at age 36, why not see if he can do it again? 

Edwin Encarnacion

Cashman doubled down on his powerful offense when he acquired Encarnacion. But he wasn't the impact player the Yankees estimated him to be, especially in the postseason. He was just 1-for-18 with 11 strikeouts against the Astros in the ALCS, and since Giancarlo Stanton was injured, Aaron Boone had to leave him in the DH spot. 

Do the Yankees bring him back for some redemption? With Luke Voit set to come back from his core muscle surgery and LeMahieu available to play first base as well, Encarnacion would be the Yankees' sole DH. However, there are plenty of power bats to go around. 

Cameron Maybin

Another stud Yankee replacment this season, Maybin hit himself into the conversation of bringing him back. With a .285/.364/.494 slash line with a career-high 11 homers and 32 RBI, he may have rubbed the Yanks the right way. 

But he could be battling Gardner as the lone outfielder the Yankees decide to bring back. There's a ton of depth in the outfield, but Gardner and Maybin have center field experience to fill in for Hicks. Gardner has more versatility at the left side of the plate and his speed on the base paths. 

Make no mistake, though: Maybin's performance should have other teams interested. He'll be on a roster by February. 

Austine Romine

This one is a no-brainer for me. Romine has built chemistry with the Yankees' pitching staff, and his bat has had some flashes of production -- enough to be the Yankees' solid backup catcher for years now. 

But that's for me. If Romine wants to test the waters a bit instead of keeping his mind set on being in pinstripes again in 2020, a few teams could make him a fine offer to potentially be their starter. Sanchez is the franchise catcher for the foreseeable future, so maybe Romine wants his own gig elsewhere.  

Cory Gearrin

Gearrin was claimed off waivers by the Yankees, and played in just one game. With the bullpen depth, Cashman should let him test his fate on the market. 

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