What would a Mookie Betts extension look like?

Tuesday was our first day out of the holiday break, and boy did we get some real live baseball news. For one thing, it was reported that the Red Sox offered J.D. Martinez a five-year deal. WOOO! That’s actual news and a thing to discuss, and that is rad as hell. Additionally, the Red Sox signed Ivan De Jesus Jr. to a minor-league deal. A real life signing! De Jesus Jr. is the player who will carry the Red Sox to their next World Series championship, of that I am sure. In case you aren’t able to tell, I am having a bit of a breakdown with this lack of action. Don’t mind me.

Anyway, while we wait for some meaningful transactions (no offense to Ivan De Jesus Jr., who I’m sure is a fine fellow) we can focus our attention elsewhere. Personally, I’ve been thinking a whole lot about extensions for Red Sox players lately. Now, there haven’t been any rumors involving potential extensions for some of the guys on the roster that have free agency on the horizon, but one has to imagine it’s at least been discussed in the front office and likely brought to the players at one point or another. Boston has plenty of intriguing pieces that could be candidates including Chris Sale, Craig Kimbrel, Drew Pomeranz, Xander Bogaerts, Jackie Bradley Jr. and even Andrew Benintendi and Rafael Devers. Those last two are even bigger longshots than the rest, of course. Beyond that group, though, one player stands out even more as someone Boston has to do everything they can to lock up on a long-term deal. That, of course, is Mookie Betts.

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This isn’t the first time I’ve mentioned a potential Betts extension, and I’ll warn you now that it almost certainly won’t be the last. As we’ve been forced to look at this roster a bit more in-depth in lieu of actual offseason action this winter, it’s caused me to look at this young core that they have. There are a lot of impressive players who should be here for years to come, but there is only one Mookie Betts. He is one of the very best players in baseball who is outstanding at just about everything. While the Red Sox are still looking for their David Ortiz replacement in the middle of the order in terms of a power bat, they needn’t look further than Betts if they’re looking for the next face of the franchise. The diminutive outfielder has the charisma and the talent to be the most prominent member of the Red Sox for the next fifteen years. It’s just up to the Red Sox front office to make sure he never plays in another uniform.

Obviously, it’s not just up to the Red Sox and Betts has to want to sign an extension now. When he gets closer to free agency or eventually hits it, the Red Sox have the financial muscle to make sure he stays, but for now it’s more or less on him. For today, though, let’s just assume he’s open to it. Maybe he’s fallen in love with this ridiculous winter we’re enduring right now and doesn’t want to live anywhere else. I don’t know. For whatever reason, he’s agreed to discuss an extension with the team. What would the final result end up looking like?

To try and figure this out, I figured the easiest method would be to take a look at some recent high-end extensions of young stars. Obviously, that’s not a huge list but there are some examples. It’s tough to define what a “star” is, of course, but it’s not hard to delineate by cash money. I looked over the last five years of extensions using MLB Trade Rumor’s Extension Tracker and filtered out to find only extensions that totaled at least $60 million and went to players with no more than 4 years of service time. For reference, Betts has three years and 70 days of service time. Below is a table of the extensions that fit this criteria.

So, let’s look at these players very quickly and remember where they stood when the extensions were signed. Wil Myers was coming off a strong, All-Star season and entering his age-27 season while also having the added bonus of still having plenty of shine from his prospect days. Kyle Seager was also entering his age-27 season and also coming off his first All-Star season, though he had a stronger major-league track record than Myers. Mike Trout....well, he was Mike Trout entering his age-22 season. Freddie Freeman was entering his age-24 season and coming off a true breakout season. Elvis Andrus was just starting his age-24 season and while he hadn’t been a star at the plate he hit pretty well while flashing a great glove. Finally, Buster Posey was coming off a World Series title and an MVP award entering his age-26 season.

David Price could be the most important Red Sox player

Photo by Omar Rawlings/Getty Images

Photo by Omar Rawlings/Getty Images

So, a few quick observations on this list. For one thing, it’s clear that extensions aren’t nearly as common for stars as they were even a couple years ago. There were two seasons separating Myers and Seager on this list. Second, most of the players who signed these extensions have worked out. Andrus could be debatable, though he’s still a strong defensive player and is coming off a good year at the plate. The jury is still out on Myers, too. Finally, Betts has better standing in my opinion than anyone on this list besides Trout and Posey.

Okay, with all of that out of the way, let’s get to the final point. What would the extension look like? Using the other deals as a template, somewhere in the six to eight year range makes sense. If Betts were to sign a six-year deal starting in 2017, he’d hit free agency again as a 31-year-old, which is still young enough to get a fine paycheck. If he was looking for that chance, six years would probably be the max. If he didn’t cary about that, I could see something as long as ten years, though that is clearly a rare type of deal. As for the money, I’d look for something around where Posey signed in terms of AAV. Posey did have a little more success under his belt, particularly awards-wise, but there’s also inflation to take into account. Taking everything into consideration, I’d be looking at something like seven years and $140-$150 million for a Betts extension. Go get it done, Dave.