The fates of these two former stars serve as a warning to teams looking to lock up their best players early, although admittedly, Betts isn’t a perfect comparison. Howard was 30 years old when he inked his extension while Cabrera was entering his age-31 season. Betts is only 26 and presumably has much more of his prime ahead of him.
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On the other hand, an extension for Betts would certainly be for longer than the five years Howard received, likely topping the eight-year extension given to Cabrera. A longer deal offsets much of the benefit of Betts being younger.
Boston could expect at least a few good years on the front end of an extension but the back end still threatens to be a financial burden. Betts would be 30 by the time he reaches the third year of the extension. If his production starts to fall off around the same age it did for these other two stars, he’d be lucky to make it halfway through the new deal before he hits a steep decline.
You could argue that a five-tool player like Betts provides more value than one-dimensional sluggers like Howard or Cabrera. However, the speed that helps make Betts an elite base runner and outfielder tends to diminish earlier than power does. His all-around game is what makes Betts an MVP so the dropoff could be more severe for him once those skills start to fade.