Red Sox star Mookie Betts should lock in a contract extension immediately

With Mike Trout setting a new MLB record with his contract extension, it’s time for Mookie Betts to sign a new deal with the Boston Red Sox.

It’s time for Mookie Betts to sit down at the negotiating table and hash out a new deal that keeps him in the Boston Red Sox organization for the foreseeable future.

It probably won’t happen. In fact, Betts recently reiterated his intent to wait to discuss his contract until he hits free agency, according to The Boston Globe’s Alex Speier.

Betts assures us that he’s happy playing in Boston but doesn’t want to sell himself short by signing an early extension. He’s perfectly content to bet on himself by going year-to-year through the arbitration process before cashing in big when he hits free agency after the 2020 season. By foregoing the certainty of long-term security, Betts is banking on maximizing his earnings by waiting to sign his inevitable mega-deal.

Consider what could have happened if Betts rushed into an extension at the beginning of the offseason, fresh off an MVP campaign and a World Series parade. Seems like an opportune time to cash in, right? Betts would have certainly aimed to top Giancarlo Stanton‘s 13-year, $325 million contract extension, which at the time was MLB’s largest total value contract. He probably would have succeeded, only to be disappointed when Manny Machado signed his 10-year, $300 million deal with the Padres. Even if Betts had managed to surpass Stanton for the largest total value, he wouldn’t necessarily have met Machado’s $30 million average annual value.

Machado’s deal set a new standard as the highest total value contract given to a free agent, a record he held for about five minutes before Bryce Harper topped it with a 13-year, $330 million deal. These superstars raised the bar for total value and average annual value for elite position players, benefiting players like Betts who venture into free agency after them. It behooved Betts to wait for his moment, allowing others to keep raising the bar that he intends to hurdle when the time comes.

Then the Mike Trout extension happened. The Los Angeles Angels star obliterated the standard set by his peers with a massive 12-year, $430 million deal. I previously discussed why Betts won’t break Trout’s record and stand by that assessment. However, that was assuming he waits for free agency when he’s 28 years old. The gist of the argument is that by that age, Betts will be hard-pressed to demand more than 10 or 11 years and it’s unrealistic to believe his average annual value will top Trout’s contract by enough to make up the difference of at least one fewer year on the deal.

If Betts signs an extension before this season? Different story. The 26-year old Betts is a year younger than Trout and the same age as Harper. He can make a compelling case for deserving at least a 13-year deal now, which seems far less plausible in two years when he has fewer prime seasons remaining.

Let’s say the Red Sox convince Betts to sign a 13-year, $440 million deal. The $33.8 million average annual value tops anyone who isn’t named Trout ($35.8 million AAV), which seems fair given that Trout is still considered the best player in baseball. Betts still earns the honor of the highest total value, accomplishing his goal of raising the bar. The Red Sox lock up their best player for the rest of his career while spreading his salary over a longer period to reduce the AAV for luxury tax purposes, similar to what the Philadelphia Phillies did with Harper.

The hesitance by Betts to negotiate now is the same as it was to begin the offseason. What if someone else raises the bar again after he signs his deal two years earlier than he needed to? With Trout off the board, this should no longer be a concern.

Next year’s crop of free agents includes several appealing options but nobody who is going to shatter records. Nolan Arenado was expected to headline the 2019-20 class until he signed an 8-year, $260 million contract extension this winter. The top position player available next year might be Paul Goldschmidt, who will be 32 years old by then. J.D. Martinez could opt-out of his deal to join him on the market but he’s a month older than Goldy and primarily a DH. Xander Bogaerts and Anthony Rendon will be paid handsomely but nowhere near Machado/Harper territory, let alone Trout.

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The following year will see J.T. Realmuto and George Springer among the rising stars hitting the market at the same time as Betts, barring extensions. It would take a significant leap by one of the young players in that class to even put them in the conversation.

The only competition Betts had in the battle for the biggest contract was Trout, who is now off the board. Nobody else is raising the bar higher than it is now. That means there’s little to gain by waiting to sign. Sure, another MVP award or two could increase the average annual value Betts can demand, possibly surpassing Trout’s salary. Waiting to find out almost certainly means a shorter contract than he could get now though. Even if you factor in the $20 million he’s scheduled to earn this year, whatever he makes in his final year of arbitration, plus any realistic deal we project him to earn as a free agent in two years, it may not add up to what he can earn now.

There’s also a tremendous downside in waiting. What if he gets hurt? What if his production dips closer to his 2017 numbers rather than another MVP-caliber year? His value is as high as it’s ever been and it’s hard to see how it gets much higher in the next two years.

The mentality of betting on yourself is admirable and should push Betts to another outstanding season. I can’t fault him for his desire to keep waiting yet I can certainly disagree with his logic for doing so.