Yankees: What are their plans for the rotation beyond the 2020 season?

Six years ago, today, the Yankees announced that they had signed standout Japanese ace, Masahiro Tanaka to a seven year/155 million dollar contract.

Over the past six seasons, Tanaka has been the Yankees most consistent pitcher and is, in fact, the only pitcher on the club remaining from the 2014 season. In the regular season, he has been very decent, but when the games count the most, he’s been money. His playoff numbers are historic, and he always seems to rise to the occasion in October.

Now, six years later, we are entering the final year of Tanaka’s deal as well as fellow starting pitcher, James Paxton. Paxton, who was acquired in a trade last winter which sent Yankees’ prospect Justus Sheffield to the Mariners, had a very good first season in New York. He had a few bumps in the road, but once he got past those, he finished the season very strong and showed what kind of a pitcher he is and still can be.

Both of these pitchers are integral parts of this Yankees rotation, and next offseason will be an interesting one for New York. The Yanks just broke the bank paying Gerrit Cole, and they will need to start thinking about preemptive extensions for their young stars. Additionally, last year’s team MVP DJ LeMahieu will be hitting the market, and he is what made that offense click in 2019.

Will they be able to resign both James Paxton AND Masahiro Tanaka? Will they be able to afford even ONE of them?

The market for free-agent pitchers in 2020 will be very thin…

One can argue, that Paxton and Tanaka are the two best starting pitchers available! Other notable pitchers include Marcus Stroman, Mike Minor, and Trevor Bauer. Any one of these five pitchers would probably be the fifth or sixth best starter in last years, free-agent class…

Additionally, the SP trade market is very weak and thin, and I don’t think there is anyone who is significantly better than Paxton and Tanaka. With this in mind, we have to assume that teams that are in need of good starting pitching will be bidding for whomever they think is the top pitcher in this class. Therefore, signing both Paxton AND Tanaka might prove to be quite difficult.

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If the Yankees can trade away J.A. Happ’s contract, they may have an easier time signing both, but it really depends on a couple of factors during the 2020 season:

• Both pitchers’ performances (obviously)
• Both pitchers’ health (especially Paxton)
• The progression of the Yankees’ top prospects (and Jordan Montgomery)
• How the other prospective free-agent pitchers perform

Personally, I have always been a fan Trevor Bauer and I would love to see him in the pinstripes, but he has not done it in New York, while Paxton and Tanaka have.

Frank Sinatra said it best in his classic, “New York, New York”:

“If I can make it there, I’ll make it anywhere”. 

If you find guys who can make it here, do whatever it takes to keep them here.