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The tricky part about signing Dallas Keuchel

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There is little about signing Dallas Keuchel that is simple.

MLB: ALCS-Boston Red Sox at Houston Astros Troy Taormina-USA TODAY Sports

Dallas Keuchel is still on the open market. Today is March, 15th, the season starts on March 28th, and one of the best pitchers (two, actually) in this year’s class is still unsigned. That’s not great.

This isn’t unprecedented of course. It was almost a year ago, March 20th, 2018 that Alex Cobb reached his deal with Baltimore. Keuchel is most definitely hoping for a Cobb-like outcome. Despite waiting about as long as physically possible, Cobb still ended up getting a plenty respectable 4 years/57 million from the pitching-desperate Orioles. Keuchel would take that deal and sprint out the door at this point.

But there’s a tricky aspect to a potential Keuchel contract. It’s certainly not unique to just him as other pitchers have found themselves here, but it is worth noting because of the conundrum in which he and his potential suitors find themselves.

Keuchel wanted a 5-year deal. That’s been reported enough by enough sources that’s it probably safe to call truth. It’s also safe to say, at this point, that isn’t going to happen. Most teams have very little interest in giving any pitcher a 5-year free agent deal, much less those who reside on the wrong side of 30.

So the conventional wisdom says take a shorter term deal. Keuchel most likely has a few different 2-year deals to choose from but this where the tricky part comes in. If Keuchel isn’t going to get the long term deal he wants, then a 1-year deal makes more sense for him than a 2-year deal. He can bet on himself to have a good year in 2019 and hit the open market next year and still only be 32. Where a 2-year takes him to 33, and makes it that much harder to get the multi-year deal he seeks.

So you might be saying, okay why doesn’t he just take a 1-year deal then? Well, teams might not be offering a 1-year deal. You see, Keuchel has draft pick compensation attached to his free agency. That means teams are giving up a draft pick to sign him. And because of how the system is set up, those teams lose the same pick regardless of whether they sign him to a 1-year deal, 2-year deal, or 5-year deal. It’s easier to stomach the loss of that pick knowing the player you gave it up for is going to be around for more than 1-year.

So 1-year deals don’t really make sense for the teams. 2-year deals don’t really make sense for Keuchel. And anything over 3 years most likely isn’t happening. You see the dilemma. There’s a very small sweet spot that can potentially make sense for both parties.

I’ve said a few times, something around 3/50M makes sense for everyone but, there are teams who don’t even want to go to 3 years. Now he could still sign a 2-year deal if he concedes or a 1-year deal if a team concedes but a contract for him is a bit trickier than it seems.

We’ll know soon enough.