Red Sox: Mookie Betts extension would be too risky for both sides

History tells us extending a massive contract to a superstar too early can be risky, which should make the Red Sox hesitant when it comes to Mookie Betts.

Let’s get this out of the way early. The Boston Red Sox will not sign Mookie Betts to a long-term extension this winter. He’s going to get a one-year deal, either by reaching a mutual agreement or through an arbitration hearing, then follow the same path next year before hitting free agency in 2021.

It’s not that the front office isn’t interested in locking up the reigning American League MVP. We can’t criticize Dave Dombrowski for “failing” to get a deal done when the player has no interest in sitting at the negotiating table. Betts has made it abundantly clear that he’s willing to bet on himself, going through the arbitration process year after year until he earns the right to test free agency.

Calm down, this isn’t a sign that Betts is eager to leave Boston. It’s simply the path he sees as the best option to maximize his earnings. He’s right to assume that, so long as he believes in his ability to play at this elite level between now and free agency.

Contract negotiations are typically set on precedent. Why would Betts want to set the bar now when he can wait for others to do so before he leaps over it?

The current free agent landscape is headlined by Bryce Harper and Manny Machado, a pair of superstars seeking record-breaking deals. We’ve heard rumors of Harper potentially landing a massive $400 million deal. While he may ultimately fall short of that figure, if Harper is worth anywhere near that amount then how much is Betts worth?

Harper or Machado could set a new precedent for what elite free agent position players should be paid. Nolan Arenado or another high-profile free agent could top that next winter. There’s little incentive for Betts to be the one that sets that precedent two years ahead of when he’s eligible for free agency. Not unless he’s concerned about a dropoff in production or injury wrecking his value, which clearly he’s not too worried about.

Those factors are concerns the team would need to consider if Betts were hypothetically open to an early extension. History tells us that locking up a superstar two years before they hit free agency carries significant risk.

The prime example is the disastrous five-year, $125 million extension the Philadelphia Phillies gave Ryan Howard in 2010 when he still had two years left on his deal. Howard was a former NL MVP who finished top-five on the ballot in four consecutive seasons leading up to the extension. He finished 10th in MVP voting in 2010 and 2011, the last two seasons of his original deal.

Howard suffered a devastating Achilles injury during the 2011 postseason, leading to the early demise of his career. He returned to play in 71 games the following year but clearly wasn’t the same hitter and never was again.

Howard produced a brutal -1.2 WAR in the first year of his new deal and was a shell of his former self for the rest of his career, which mercifully came to an end after the 2016 season. Howard hit .226/.292/.427 and produced -4.5 WAR over the five years that covered his extension. He had a sub-.800 OPS in each of those seasons and never topped 25 home runs in any of them.

The injury played a significant part in Howard’s decline but he never came close to recapturing his previous form once his Achilles recovered, by which point he was approaching his mid-30’s. It’s fair to say his next contract would have looked a lot different had the Phillies waited until Howard was eligible for free agency.

While it’s hard to imagine a contract backfiring as much as the Howard deal did for Philadelphia, Miguel Cabrera receiving an 8-year, $248 million extension in 2014 – two years before he would have hit free agency – was even more shocking.

Cabrera was coming off back-to-back MVP campaigns and in 2012 he became the first AL hitter in 45 years to win the Triple Crown. He cashed in when his value was at its peak to secure a deal that will last until he’s at least 40 years old.

Predictably, the deal isn’t working out for the Detroit Tigers. Cabrera remained an elite hitter for what would have been the remainder of his original deal, finishing 9th in MVP voting in 2014 and winning another batting title in 2015. Unlike Howard, Cabrera remained productive after the extension kicked in, hitting .316 with 38 homers in the first year of the new deal.

One year later, Cabrera hit a sharp decline. He hit career-lows with a .249 average and .728 OPS in 2017. His 16 home runs were the fewest he had tallied since his abbreviated rookie year. While he showed signs of bouncing back last season, injuries limited Cabrera to only 38 games.

It’s hard to imagine Cabrera returning anywhere near his previous form at age 36 yet Detroit still owes him $154 million over the next five years. The Tigers got one great year out of this extension followed by seven seasons in which he’ll almost certainly be considered vastly overpaid.

This isn’t to suggest that the Red Sox shouldn’t plan ahead for a future with Betts. He’s one of the best players in baseball and one of the best the franchise has seen in decades. We should want to see Betts wearing a Red Sox uniform for the rest of his career.

There’s just no reason to commit to that now. Too much can change over the next two years. A career-altering injury could derail his value before the extension even kicks in. He could revert to his 2017 level at the plate instead of the batting champion we saw this year.

Extending Betts now would be paying for his peak value coming off his MVP season. We always hear warnings about teams shelling out massive deals to free agents after a career year. Ask the New York Yankees how the Jacoby Ellsbury deal is panning out for them. If overpaying for a potential outlier season is risky, doing so when the player is under team control for two more years is downright foolish.

The only advantage of an early extension would be if there was an opportunity for a bargain. If Betts wanted to lock in long-term security now, he could sign an extension for below market value. The Red Sox get a superstar on a team-friendly deal and Betts protects himself against the career-crippling worst-case scenario.

Except Betts has made no indication that he’s willing to accept a hometown discount or play it safe by signing early. Boston could offer him the moon and Betts may still decline, preferring to wait and see if the market for superstar players hits new highs two years from now.

By agreeing to an early extension, Betts risks missing out on a bigger payday down the line if other stars raise the bar in the next couple of years. Locking him up now at current market rates potentially saves Boston a few million bucks in the long run but not without the risk of the contract becoming an albatross soon after the extension kicks in. It just doesn’t make sense for either side to make that commitment two years before they need to.

Boston’s best option is to let Betts play it out his way, then negotiate a new deal based on his perceived value in two years. There’s some risk that he could bolt to a rival team if given the chance to test free agency but the Red Sox need to trust that their winning culture, leadership, and a city he has come to embrace will be enough to entice him to stay.