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What would extensions look like for the Yankees’ impending free agents?

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With Didi Gregorius, Aaron Hicks, and Dellin Betances nearing free agency, what would it take to lock them up?

MLB: Baltimore Orioles at New York Yankees Wendell Cruz-USA TODAY Sports

Earlier this week, I looked at the Yankeescandidates for extensions. Sure, it would be great to lock up the likes of Aaron Judge and Luis Severino, but with those players so far from free agency, it’s tough to pin down extensions for them. I focused on the Yankees that were closing in on free agency: Didi Gregorius, Dellin Betances, and Aaron Hicks.

I concluded that Hicks looked like the best long-term bet, though the Yankees certainly have the financial wherewithal to keep all three in-house. Now, the question is what it would actually take to keep these guys. What does recent history suggest about the likely contract demands of Betances, Gregorius, and Hicks?

Betances is the most difficult to peg, as there just aren’t that many incidences of top relievers signing extensions close to free agency. The best examples we have are for lesser players. Brad Hand signed a three-year, $19.5 million deal before this season, two years ahead of free agency, essentially selling one free agent year for about $7 million. In 2017, Pedro Strop signed a two-year, $11.85 million extension one year before free agency.

Neither of those pitchers fit Betances’ profile as a genuinely elite reliever. Instead, it’s probably best to take a look at the top of the free agent market for relief pitchers. Prior to 2017, a 30-year-old Aroldis Chapman received a five-year, $86 million deal with an opt-out after three years from the Yankees. Chapman had maintained a 233 ERA+ and fanned 15 batters per nine in his three seasons prior.

Also before 2017, a 29-year-old Kenley Jansen signed a five-year, $80 million deal with the Dodgers, coming off a three-season stretch in which he posted a 162 ERA+ and struck out nearly 15 batters per nine. Betances will be 31 next year, and has a 152 ERA+ and a 15.2 K/9 rate over the past three seasons. Since he will be a couple years older than Jansen and Chapman were upon reaching free agency, is still a year away from free agency, and has been slightly worse than those two, Betances can expect to come in somewhat behind Chapman and Jansen.

Based on that, an extension for Betances would probably tack on an extra three or four years, at annual rate around $15 million. Call it four years, $60 million, or three years, $51 million, something along those lines. Betances is likely looking at top of the market reliever money for a slightly shorter term.

Gregorius and Hicks should be easier to peg, as there is a longer track record of players of similar caliber signing extensions at their positions. Gregorius actually has a pretty excellent recent comp in Jean Segura. Midway through 2017, the Mariners signed Segura to a five-year extension that bought out Segura’s final year of arbitration and four free agent years at a cost of $70 million.

Segura profiled as a legitimate first-division starter at shortstop when he signed his extension, and would’ve been a free agent at age-29. Likewise, Gregorius will be a free agent at 30 and has established himself as a high-quality starter up the middle.

Brandon Crawford also offers a reasonable comp. Crawford signed a six-year extension two years prior to free agency, essentially selling four free agent seasons. his age-31 through age-34 seasons, at a price of $15.2 million. In either case, we’re looking at good shortstops fetching around $15 million per year ahead of free agency.

Complicating matters, of course, is Gregorius’ offseason Tommy John. Because of the injury, the Yankees would probably ask Gregorius to take either less money or a shorter term than his peers did. Gregorius may have exceeded Segura’s $70 million offer had he stayed healthy, but instead, three or four years at around $15 million feels right for Gregorius.

I called Hicks the best extension candidate, and consequently, he should be the priciest to extend. The first comp that comes to mind happened earlier this year, as Charlie Blackmon signed a six-year extension that guaranteed him at least $94 million over five free agent years, with player options on the final two years.

Blackmon isn’t a perfect comparable, though, as he was coming off a two-season stretch in which he posted a 136 OPS+ and over 10 WAR. Hicks has been great over the past two years, but has maintained a 123 OPS+ with 8.6 WAR over that span. On the other hand, Blackmon would have hit free agency at age-32, while Hicks will be 30 upon becoming a free agent. Moreover, Blackmon’s value was tied up in his bat (a bat that did regress last year), while Hicks brings a wider range of skills to the table, including superior speed and defense in center field.

A better comp might actually be staring us right in the face. One year before free agency, Brett Gardner signed a $52 million extension with the Yankees that bought out his age-31 through age-34 free agent seasons. In the two years prior to signing, Gardner put up 8.2 WAR. He was a lesser hitter than Hicks, but in terms of age and overall value, the two were in similar positions as they stood one year from hitting the market.

Since the market slightly favors offensive output, and as four years of inflation have passed, it’s fair to expect Hicks to fetch a bit more than what Gardner received. Call it about four years, around $17 million per.

These are simply estimates based on the most recent precedent. What these players actually would get on the market could differ dramatically. Even so, none of these three profile as someone the Yankees would truly have to break the bank for to sign to an extension. Such an extension for any of them would bring the benefit of immediate, long-term financial security for the player, and a locked-in commitment to a quality performer for the team. Brian Cashman has indicated he would broach extensions with each of them, and any fruitful negotiations would be a welcome sight.