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Yankees extension candidate: Didi Gregorius

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Now would be a perfect time for the Yankees to start talking extension with Didi Gregorius.

Kim Klement-USA TODAY Sports

Spring training is a time when teams try and work long-term deals with their pre-free agent and pre-arbitration assets. In the past week, the Cardinals and Royals have come to terms on multi-year contracts to a pair of 25-year-olds. St. Louis second baseman Kolten Wong, fresh off a solid sophomore season, got $25.5 million to pass on his first two years of free agency and stick around through 2021 if a club option gets exercised. Kansas City catcher Salvador Perez got time and cash tacked on to an existing and infamously team-friendly deal. In exchange for an extra two seasons of club control, he'll get $52.5 mil between 2017 and 2021.

Missouri's two teams, both near the top of the list among MLB's model franchises these days, are betting on their young talent by locking down the bulk of their primes. By guaranteeing years and money before they absolutely have to, they're hoping to hold on to productive players at below-market prices in the future. For all Hal Steinbrenner's recent talk about fiscal restraint and big picture thinking, that's a bet the Yankees are usually unwilling to place.

We've heard for years about the Yankees' "no extensions" policy. It's a relic from the George Steinbrenner era grounded in the premise that there's no need to take earlier than necessary risks because they could simply outbid all comers in free agency. That logic was always flawed - by waiting longer they paid more on deals that covered fewer prime and more decline years - and it makes even less sense now that the open wallet policy has been rethought.

Ironically, when the Yankees have been proactive, it's produced some outstanding results. The six-year deal they inked Robinson Cano to in 2008 bought out four arbitration years and two free agent years via club options and yielded 22.6 fWAR. A five-year, $51 million deal for Jorge Posada in 2002 netted two MVP-like campaigns in ’03 and ’07 and kept the catcher from free agency until very late in his career. The granddaddy of them all was Derek Jeter’s ten-year, $189 million pact signed just before camp opened in 2001. It was the second largest guarantee ever at the time, but it ended up a bargain.

That brings up another New York shortstop in Didi Gregorius. The Yankees won year one of last winter's three-team swap that shipped out Shane Greene in every way you can win a trade. Didi led the team in 2015 fWAR at 3.1, posted a strong 7.9 UZR/150 and hit a respectable .265/.318/.370, including .294/.345/.417 with a 109 wRC+ after the All-Star break. Last month he avoided his first of four trips to arbitration as a super two by agreeing to a $2.425 million salary for 2016. The Yankees probably love the idea of paying that little for a guy who seems to be trending up. By not signing him for a longer term, though, they’re passing on an opportunity to make him cost-effective for most of his prime.

The Wong contract isn’t a perfect comparable, since he wasn’t yet arbitration eligible, but like Didi he hasn’t had a breakout year yet but is improving and would have been a free agent after 2019. Andrelton Simmons’ seven-year, $58 million with Atlanta also came earlier in his salary progression, but could also be used as something of a framework, as could the eight-year, $60.57 million deal for new teammate Starlin Castro, which started with the Cubs in 2012. The cost of buying out the 26-year-old Didi’s final thee arbitration years and possibly two free agent years would be higher than any of those, with an AAV that would probably exceed $10 million per, but that's still cheap compared with what free agents get now and will get in 2020 and beyond.

Jorge Mateo will be on the Yankees’ minds when they think about Didi’s future, but the 20-year-old's presence is more of a reason to sign him than not to. Mateo is a better prospect than Gregorius ever was, and he could conceivably shove him out in the not-too-distant future, especially since the Yankees are obligated to Castro and Chase Headley for more years and more money. If the team does ultimately make the Didi to Jorge switch, having the former locked into a team-friendly deal rather than inching closer to free agency would give his trade value a nice bump.

Simmons is fantastic defensively, but not a particularly good hitter. He’s never had an OPS+ over 90 in a full season, he’s not a threat on the base paths and he’s shown zero power the past two years. Still, for the Angels, the prospect of filling their shortstop hole for the next five years at a reasonable $53 million was enough to part with Sean Newcomb, a top-10 pitching prospect per Baseball America, and Chris Ellis, a former third round pick who could be pitching in Atlanta later this year.

Obviously these deals don’t always work out as planned. If the Yankees do a long-term deal and Didi regresses to his 2014 Arizona or 2015 April form, they’ll have a problem on their hands. The Rangers went all kinds of all in on Elvis Andrus after an All-Star 2012, and now they’re stuck with one of the more horrific contracts in all of baseball. The Padres thought they had a winner when they signed Jed Gyorko for $35 million after a good rookie year, but they ended up having to pay to send him to St. Louis (where he’ll probably excel because Cardinals).

Here at home, Brett Gardner isn’t overpaid at $39 million over the next three years, but he isn’t a steal either, and the Yankees could have used a bit more outfield and payroll flexibility. Regardless, the Yankees are known for taking much bigger and less shrewd chances than the $50-$60 million it could cost to secure Gregorius through the early 2020’s. If they're committed to acting more like a mid-market team, these are the kinds of moves that smart mid-market teams tend to make.