Money wins championships, but money also raises expectations – the New York Yankees franchise is very familiar with both of those aspects, although higher expectations have been the only aspect to come true as of late. With a World Series drought on their hands, the Bronx Bombers have yet another pivotal offseason ahead of them.

2009 marks the last time that the Yankees won the World Series, which is a long time for that franchise. Their storied history and high payrolls aside, the talent that this team has, has definitely fallen short since then, but adding a high-priced starting pitcher could reverse those fortunes.

Having helped lead the Houston Astros to this season’s World Series, where they fell to the streaking Washington Nationals, hurler Gerrit Cole is a free agent and looking to cash in on his career-best 2019 season. With the potential and all likelihood of breaking the record for the largest free agency deal for a starting pitcher in the history of the MLB, not many teams have that type of money built into their budget.

Thankfully for the Yankees, their willingness to consistently go over the luxury tax threshold means that they can realistically sign any player that they want, which always keeps them in the hunt for big-time free agents. That is no different here for Cole, who would instantly push this Yankees team to the front of the pack and become the favorites to represent the American League in the World Series.

Reports of C.C. Sabathia having already conversed with Cole about coming to the Yankees has heated up the rumor mill just a bit this week, but with the season having just ended, the words ‘collusion’ and ‘tampering’ will be thrown around on a consistent basis until players are legally able to enter free agency, talk with teams and sign their new contracts.

If Cole were to join the Bronx Bombers, they would have a five-man rotation that looks something like this:

1 – Gerrit Cole
2 – James Paxton
3 – Masahiro Tanaka
4 – Luis Severino
5 – J.A. Happ

Besides using the words like unstoppable and incredible to describe how dominant their rotation would be if it actually did look like this for 2020, it would also be a very pricey rotation. But Brian Cashman, who seems to do money snow angels every time the Winter Meetings begin, lives and dies on a money hill, and so does his team, so spending a ton of money to only upgrade one area of this team is not a foreign concept to the front office.

Even though certain areas, like infield and outfield depth, are more important and pressing, shiny objects always draw the Yankees in. Starting pitching seems to always be one of those objects, so it will be interesting to see how much Cole gets this winter and if it actually ends up coming from the Yankees.