As a yankees fan i am on the fence about this move. I have seen the yankees hand out large contracts to free agents in the past and get burned. Jacoby Ellsbury prob being one of the worst in recent memory. Just seems like this big free agents rarely deserve all the money they get.
Also there will be a bidding war between the yanks and the angels who have deep pockets and said they would be willing to spend here too. I rather see the yanks develop their own prospects from the farm system and resign those guys. Just like they did with pettite, rivera, jeter and posada in the 90s and 2000s.
I trust Cashman to handle this well tho. i think he is a top 5 GM in baseball.