Free agency is vital to the Yankees — 2019-20 free agency that is.
Of course they must delve into starters in the coming market and determine if they can retain Zach Britton or David Robertson or decide to hunt elsewhere to maintain their valuable relief depth.
Part of this offseason, though, has to be focusing on five key players who will be entering their walk year in 2019: Dellin Betances, Sonny Gray, Didi Gregorius, Aaron Hicks and Austin Romine. The Yankees haven’t locked up a player prior to free agency since Brett Gardner in 2014, but a priority this winter should be getting Gregorius extended long term and at least seriously looking at it with Hicks and Betances.
1. Gregorius: What more would you want for an extension candidate?
He has gotten better in each of his four Yankees seasons. Gregorius not only has demonstrated he can flourish in New York, he did it as the successor to Derek Jeter. He has evolved into an important clubhouse voice just as the terms of Brett Gardner and CC Sabathia are nearing an end. He is a two-way player. He is a lefty hitter among the Yankees’ overly righty lineup. He is a serious-minded gifted athlete who should age well.
Plus, unless the Yankees are committed to moving Gleyber Torres to shortstop in 2020, there is no obvious internal replacement.
Think five years at $70 million as a starting point. That is what Jean Segura received in an extension from the Mariners, and there are many similarities with him and Gregorius, beginning with the fact they were born 27 days apart in 1990.
Over the past four years, Gregorius has a .765 OPS and 13.3 Wins Above Replacement, Segura .758 and 13. Segura has more speed, Gregorius more power and they are strong defenders.
Segura was extended after he had agreed to a contract for 2017, so his five-year extension began in what would have been his walk year this season when he was paid $12 million ($9 million in salary and a $3 million signing bonus). Didi would be entering his walk year and is likely to receive $12 million-ish in arbitration.
Two years have gone by since the Segura deal was struck, and Gregorius is vital to the Yankees, so perhaps the Yankees have to guarantee a sixth year (including Segura’s option, his deal would be six years at $86 million), or sweeten the average value a bit. But this is the ballpark, and it is a ballpark the Yankees must play in.
2. Hicks: He has similarities to Lorenzo Cain — athletes who battled injury early in their careers whose baseball skills refined with time to bring great overall value. Both qualified for the batting title for the first time in their age-28 season, which Hicks just completed. Cain is the better hitter and base stealer, Hicks has more power, is a switch-hitter and is a good defender — though not in Cain’s upper-elite category. Cain has a super hitting eye, but Hicks’ is better.
Cain did not hit free agency until he completed his age-31 season, Hicks will do so two years younger. Cain received a five-year, $80 million pact from the Brewers off of a walk-year salary with the Royals of $11 million. Hicks will be paid about $6 million next year. So he probably is looking at something south of Cain if an extension were done, perhaps five years in the $60 million-$70 million range, but if you believe he will age like Cain, that is a good deal for the Yankees.
And a brief aside here: The Red Sox are in a like situation with somewhat similar players this offseason, as both shortstop Xander Bogaerts and Jackie Bradley Jr. will be facing their walk years in 2019.
3. Betances: Attention gets focused on Betances’ occasional fits of wildness/ineffectiveness, but he has mostly been an elite reliever for five years.
How elite? This is him vs. a mystery reliever over the past five years:
Betances: 2.22 ERA, 40.3 strikeout percentage, 10.8 walk percentage, 11.9 WAR.
Mystery Man: 2.30 ERA, 40.5 percent strikeout, 10.2 walk, 10.7 WAR.
The mystery man is Craig Kimbrel, who is likely to get the highest free-agent relief deal this offseason. Yes, Kimbrel has the saves, but Betances has roughly a season more worth of relief innings (68) in that time. The two had similar results this year and were born two months apart in 1988.
Would the wildness becoming more permanent scare me if I were the Yanks? Yep. So would a long-term bet on someone who throws as hard as Betances. But he is a New York native who has become an important leader, too. Britton and Robertson are free agents now, Aroldis Chapman is unlikely to opt out after next season, but he could. The Yankees have to worry enough about their long-term bullpen that they at least have to see if Betances would be willing to do, say, a four-year, $52 million-ish deal, don’t they?
Keep in mind that Betances and the Yankees have publicly fought over his salaries in the past.
4. Gray: The Yankees are not extending him, they will try to trade him. Interested teams will notice that on the road, Gray had a 3.17 ERA and .614 OPS against, and believe there is still a legitimate starter in there. So don’t expect the Yanks to take just anything to get rid of him.
5. Romine: One item the Yankees should seek in return for Gray is an upper-level minor league catcher. They drafted Anthony Seigler and Josh Breaux with their first two picks in June, but neither catcher is close to helping. Kyle Higashioka is probably no more than a depth piece. Romine has emerged as valuable enough as Gary Sanchez’s caddie that the Yankees should at least consider whether a two-year, $4.3 million pact, like the Rangers gave Robinson Chirinos two years ago, works. Or does Romine want to play it out and see if a team values him as a starter in the 2019-20 free-agent class?
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