In case you hadn't heard, Robinson Cano is a free agent. More often than not, re-signing a player of Cano's caliber would be a forgone conclusion. Why wouldn't one of the richest teams in the league retain the services of far and away their best player? With the Yankees' stuffed coffers seeming being made less available than in the past and Cano's rumored demands a touch extreme, there is some doubt to whether he will be in pinstripes next season. He wouldn't be the first All-Star the Yankees let walk in his contract year. (Your usual disclaimer: this is far from a complete list.)
Nick Swisher (2013)
With Yankees: 14.4 fWAR over 4 seasons
Over new contract: 2.4 over 1 season (3 years left)
Swisher put together four good seasons for the Yankees before opting for a four-year, $56 million deal from the Cleveland Indians. Offering four years with that kind of money to a 32-year old is far from a no-brainer, but OBP machines like Swisher tend to age better than most and he was productive in his first season in Cleveland. The Yankees' failure to replace him with a league-average bat was more the problem than losing Swisher himself.
Andy Pettitte (2004)
With Yankees: 38.9 fWAR over 9 seasons
Over new contract: 10.2 fWAR over 3 seasons
This is the one that hurt the most. As George Steinbrenner famously wined and dined free agent outfielder Gary Sheffield, Pettitte opted for a three-year deal with his hometown Houston Astros that netted him a little over $30 million. He was well worth the deal in Houston and helped lead the Astros to their first World Series appearance while the Yankees, ninth in ERA in 2003, settled into 21st over the '04-06 seasons.
Jimmy Key (1997)
With Yankees: 12.1 fWAR over 4 seasons
Over new contract: 4.3 fWAR over 2 seasons
This was essentially a swap of two pitchers, as the Yankees decided to sign away David Wells from the Baltimore Orioles and the O's replaced Wells with Key. Key had an excellent '97 season but retired after a poor '98 campaign, and Wells was a Cy Young contender in 1998 before being the centerpiece of the Roger Clemens trade. So score that one for the Yankees.
Graig Nettles (1984)
With Yankees: 43.6 fWAR over 11 seasons
Over new contract: 5.2 fWAR over 3 seasons
1983 was another solid campaign for Nettles (120 wRC+) but he was turning 39 and was not the dominant gloveman at third base he once was. Nettles signed with the San Diego Padres, whom he helped to the 1984 World Series while the Yankees had handed the third base reins over to young slugger Mike Pagliarulo by mid-season.
Reggie Jackson (1982)
With Yankees: 18.2 fWAR over 5 seasons
Over new contract: 4.5 fWAR over 5 seasons.
Mr. October had worn out his welcome in the Bronx by 1982, so he went back to the state of California for another massive contract. He would hit home run number 500 for the Angels, but he wasn't nearly the force there that he was in New York, slugging under .410 in three of his five seasons with his new team.
As you can see, the Yankees have a pretty good track record of deciding which quality players to let sign with other teams, but they haven't been a position player the caliber of a Robinson Cano. Nettles and Jackson were close, but were much older at the time. Players that had resumes similar to or greater than Cano's, like Derek Jeter, Bernie Williams and Alex Rodriguez, were all locked up. It will be interesting to see how far the Yankees will go to retain the services of their latest free agent superstar.