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Will any Cincinnati Reds sign a long-term contract extension this winter?

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A preview of extension season, the lesser known step-cousin of holiday season

Cincinnati Reds v Cleveland Indians Photo by Ron Schwane/Getty Images

Almost exactly a year ago, I previewed the what a winter of contract extensions from the Cincinnati Reds might hold. After all, this is a club that once built itself on the backs of those, from Joey Votto to Jay Bruce, Homer Bailey to Eugenio Suarez and Tucker Barnhart.

They had varying rates of success, admittedly. The Votto deal has been brilliant, as has the one for Tucker, mostly. Eugenio’s got off to a wonderful start before his shoulder injury and subsequent sputters, while the deals for Homer Bailey and Devin Mesoraco crashed immediately and often. Those for Brandon Phillips and Jay Bruce, once upon a time, turned out to be pretty much just fine.

You don’t see clubs that are rebuilding and losing in copious amounts dole out too many extensions, which is why they mostly petered out over the last handful of years relative to a decade ago. Of course, when we spoke of the idea last winter, that was on the backs of a playoff* appearance and free agent spending that suggested the front office and ownership finally thought they had a club worth keeping around to win some games for a bit again, even though their frugality later in the offseason showed that was merely a mirage.

One year later, we know this Reds club needs some more work to tussle with the best of the best in the game. We also know that the decently large class of potential extension candidates from last year is now a year older and a year closer to free agency, making any potential contract doled out pricier on the front end - not to mention that each player is now that much closer to the bright lights of free agency and might not choose to commit with that so near.

If some of the players I’m about to mention aren’t in the Reds sights for a long-term contract extension, they should probably be considered to be on the trade block, in all honesty. If they aren’t in long-term plans and their team control has dwindled, well, let’s just say that’s how roster management on a tight budget has to work.

Luis Castillo continues to be the player most in the potential extension spotlight. His dizzying ability to hum 100 mph heaters and fall-off-the-face-of-the-earth changeups has become the stuff of legend around the game in the past few seasons, even if he’s still not been able to tie it all together for a full season. The talent is simply rare, and even though it’s not been as good as we’ve hoped 100% of the time, he’s still been an absolutely excellent pitcher for the Reds (14.4 fWAR since his debut in 2017). He’ll be 29 in December, though, is only under team control for 2022 and 2023, and will likely command a total salary of some ~$17 million over those two years, and while it would take the most among the players I’m mentioning here to tie him down, he’d also command that much more on the trade market if shopped. Question is, do the Reds want to tie themselves to him well into his mid-30s seasons, or not?

Like Castillo, Tyler Mahle is under team control only for the 2022 and 2023 seasons before free agency, but he also only just turned 27 years old a month ago and, per bWAR (4.9 to 4.8) and fWAR (3.8 to 3.7) was the better pitcher last season. Mahle fired 180 IP and was once again a strikeout machine, though his proclivity for Ks often runs up his pitch counts early. He’s also been a Jekyll/Hyde pitcher in his home/road splits, putting up Cy Young caliber numbers outside of GABP while struggling mightily while there. Should that make him more attractive as a trade chip that could help the roster elsewhere, or does his age make offering him a 5-year deal that much more reasonable than Castillo if the Reds choose to anchor their rotation?

Jesse Winker is in that same class of ‘team control through 2023,’ though is a much more difficult situation to consider. He was drafted as a 1st rounder out of high school by the Reds, who have obviously been enamored with his ability for a decade now. He’s 28, he’s been brilliant at the plate, but has also been both injured and a defensive liability for his entire time in the big leagues. The looming potential for the DH in the National League might make extending him more palatable, but the club also has aging, lumbering sluggers elsewhere who might need that spot more often than with the glove, though the fact that he was injured yet again might give the Reds some leverage in any would-be deal struck this winter.

Extending players with just a year of service time under their belt isn’t something the Cincinnati Reds have made a habit of doing, but it’s been increasingly more common across the league in recent years. Luis Robert, Eloy Jimenez, Scott Kingery, and Evan White were inked before they ever played in the bigs, while Evan Longoria signed a huge extension just weeks after his debut in 2008. Players like Ozzie Albies, Ryan Braun, Christian Yelich, and Anthony Rizzo all signed multi-year deals just after their first year accrued, all of which seemed to pay off big time for the clubs that signed them. So while it’s not exactly been a Reds ‘thing,’ the idea that Jonathan India or Tyler Stephenson could be locked down for cost certainty (and a life-changing guarantee on the player side) isn’t at all outlandish.

Heck, I wouldn’t even be surprised to see the Reds chase Kyle Farmer with a deal akin to what the Chicago Cubs did with David Bote a few seasons back. Bote was much younger (his extension kicked in at age 27), but like Farmer was off a 1-ish WAR season and .727 OPS as a utility infielder with a feel-good story (Farmer just put up 1.1 bWAR and a .732 OPS). I’m not at all saying I would, I’m just saying this is the Cincinnati Reds we’re talking about here and they do a lot of things I wouldn’t be inclined to pursue.

Contract extensions are ways to cement new franchise cornerstones, guarantee a good chunk of money to young players who’ll likely make that (and more) anyway, and to lock in exactly how much the payroll will be impacted without letting the arbitration process throw million-dollar wrenches in those plans. Most all teams do it. The good teams certainly do, as the Houston Astros (Jose Altuve, Alex Bregman, Lance McCullers) and Atlanta Braves (Freddie Freeman, Albies, Ronald Acuña Jr.) have on display in this week’s World Series. The Reds have some good options for extensions, too, and it’s a vital winter to decide which ones should be doled out, and which players might be best on the trade market to help sustain things around here instead.