Andrew McCutchen of the Pittsburgh Pirates agreed to a huge six-year contract extension Sunday, according to Michael Sanserino of the Pittsburgh Post-Gazette. The Pirates also have an option for McCutchen's services in 2018, at $14.75 million.
The deal buys out the final four seasons during which the Pirates would have controlled McCutchen as it was and secures two years of what would have been free agency for McCutchen—three, assuming the team scoops up its option.
It was a major move, a show of good faith by the Pirates and a big step in their slow trudge back to relevance. As important was it was, though, it was roughly a third the value of the biggest extension handed out to a centerfielder this offseason. The Dodgers got Matt Kemp on a very different sort of extension, buying his final controlled year and seven free-agent seasons for $160 million.
One of the major themes of the past winter in MLB has been that teams are more eager than ever to commit to extensions that cover multiple seasons for their best players, whether to obtain a discount on arbitration-eligible players or to lock them up without letting them hit the free-agent market.
Sometimes, those moves are great ones. To speak generally, the earlier a player signs a deal, the better that deal turns out to be for the team. Other deals make little sense or are simply massive overpays.
Here are rankings and grades for the 26 multi-year extensions signed so far this winter, from one end of the spectrum to the other.