What Yankees must do to achieve October glory in 2020

If the Yankees hope to compete for a World Championship in 2020, they'll need to bring back closer Aroldis Chapman, according to our columnist Zach Gewelb (AP Photo/Jim Mone)

After watching the Washington Nationals best the Houston Astros in a highly competitive World Series, it’s fair for the New York Yankees and their fans to wonder what could have been. 

The Yankees were three outs away from forcing the ALCS to a Game 7 in Houston, and even though Gerrit Cole was looming, the Yankees would have had a legitimate chance of besting the Astros and advancing to the World Series. A clutch hit here or there, and the Yankees were in line to compete for their 28th World Series title. 

Alas, the Bronx Bombers did not get enough of those clutch hits, and now general manager Brian Cashman is left to evaluate his talented — but flawed — team heading into the offseason.

The Yankees are one or two players away from definitively being the team to beat in 2020. The onus falls on Cashman to make the right moves and put his club over the top. 

So, what moves does he have to make? Let’s start with which impending free agents the Yankees should keep, who they should let walk away, and a couple of players Cashman should target. 

Extend Aroldis Chapman: Despite blowing Game 6 of the ALCS, Chapman still had an incredible 209 season. He finished with 37 saves and a 2.21 ERA, and recorded 85 strikeouts in 57 innings. Chapman can opt out of the remaining two years and $30 million of his contract this off-season. The Yankees shouldn’t play any games with Chapman and would be wise to offer him a one- or two-year extension at about $15 million per year, bringing his contract to four years and $60 million. The Yankees need Chapman in the back-end of their bullpen, and the Cuban lefty needs the long-term security. This should be an easy call for both sides. 

Re-sign Dellin Betances: The Yankees should also keep Betances, their gigantic homegrown flamethrower. He spent most of the 2019 season hurt, which robbed him of the lucrative free agent contract he was set to receive this off-season. Now, with the chance of a big-time payday slim, Betances should re-up with the Yankees on a prove-it one-year deal that would allow him to regain his value. The Yankees’ biggest strength in 2019 was their bullpen — and that was without Betances. A healthy Betances deepens the Yankees’ pen and gives them a much better chance of October success. A one-year, $10 million deal should get it done. 

Let Didi Gregorious walk: After a miserable start to his pinstripe career, Gregorious settled in nicely and arguably became the heart and soul of the Yankees the last couple of seasons. His stellar defense, steadily improving bat, and flare for the postseason dramatics made him a fan-favorite. But the shortstop was not the same player this year after returning from Tommy John surgery. His defense slipped and he couldn’t quite settle into a grove at the plate. The Yankees can move budding superstar Gleyber Torres to short and make DJ LeMahieu their everyday second baseman without missing Gregorious. It will be tough to say goodbye to Sir Didi, but given the Yankees payroll situation, they should let him walk, giving them some extra money to play around with in free agency. 

Bring back Brett Gardner: Bringing back Gardner makes much more sense now that Aaron Hicks will be out for most of the 2020 season due to Tommy John surgery. Gardner proved to everyone that he still has something left in the tank after recording a career high 28 home runs and .829 OPS. He struggled in October, but the Yankees still value his leadership in the club house and clearly don’t trust Clint Frazier on the big league roster. Gardner wants to be a Yankee and New York would be wise to keep him. A one-year deal at about $8 million should get it done. 

Trade Clint Frazier for Jon Gray: As mentioned above, the Yankees don’t trust Frazier to get it done at the big league level. While his bat is still fearsome, his defense and antics with the media have — fairly or unfairly — taken some of the shine away from his star. If the Yankees aren’t going to start him in the big leagues, then they should trade him for pitching. The Colorado Rockies make sense as a trade partner. The Yankees should offer Frazier, and a pair of lower-level arms for Jon Gray, who has been inconsistent in Colorado, but has enough upside for the Yankees to dream on. This would allow the Yankees to acquire another starter without breaking the bank. 

Sign Gerrit Cole to a monster free agent deal: Will this happen? Probably not. George’s Yankees would make this move in a heartbeat, but Hal’s Yankees? I don’t see it. But the Yankees are so close to a title, and their core is going to start getting expensive. There is only a year or two left of cheap production from Aaron Judge, Gary Sanchez, and Gleyber Torres before they get their big paydays. The time is now for the Yankees to take advantage and be the Evil Empire they can be. Signing Cole would send a message to the rest of the league that the Yankees are going for it, and they won’t be stopped. On the first day of free agency in the 2008 off-season, the Yankees made a monster offer to CC Sabathia that completely blew everyone else out of the water. While there was still some negotiating to be done, the Yankees landed their man. Now, it’s time to do the same with Cole. A seven-year deal at $35 million per year — totaling $245 million — could get it done. 

Making these moves would put the Yankees in a terrific position heading into the 2020 season. The club will also be getting Miguel Andujar back next year and should have better luck in the health department. If so, expect the Yankees in 2020 to be the “fully operational Death Star” Brian Cashman and company expected them to be this season.

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