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

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.