There are a handful of big free agents on the market this winter, and many of them that the New York Yankees would love to sign.
Instead of waiting to the later part of winter to make moves, the Yankees should start taking serious action NOW. With everybody wrapped up in the Astros cheating allegations, there is no better time to recruit free agents and give them offers in pretty lowkey way.
They could try to keep as quiet as possible, but if information leaks out about them making early moves, then it would quickly put pressure on other teams to match and exceed the Yankees offers.
The first order of business would be retaining Brett Gardner and figuring out the whole outfield situation. If they have interest in resigning Cameron Maybin, they could probably hold off a bit on him. He likely won’t sign a contract until February.
Once they get Gardner locked up, it would be time to decide who they are going to offer on. I would love to see them get Anthony Rendon, but the likelihood of him leaving the Nationals is slim to none. So, they should try and make quick offers on Gerrit Cole and Stephen Strasburg.
I hope that Brian Cashman doesn’t try to be cheap again and lowball them. He needs to offer both pitchers solid contracts early into free agency. It puts so much pressure on other teams to match, and it would be very tempting for them to sign when they see a huge offer.
All I’m saying is that if the Yankees start making offers early into the offseason, they may have a better chance to sign the top free agents.