New York Yankees: A look at 2021 free agency

New York Yankees, DJ LeMahieu
Jun 25, 2019; Bronx, NY, USA; New York Yankees second baseman DJ LeMahieu (26) rounds the bases after hitting a solo home run against the Toronto Blue Jays during the first inning at Yankee Stadium. Mandatory Credit: Brad Penner-USA TODAY Sports

The 2020 MLB season is still a mystery as to when it will begin if it begins at all. The MLB player’s association has a deal in place with the league to get things moving once the coronavirus pandemic comes to an end. As mentioned in previous articles on ESM, the New York Yankees are in an interesting position as to what they are going to do with DJ Lemahieu, Masahiro Tanaka, and James Paxton, all set to become free agents following the conclusion of this season. They have tough choices to make whether they want to resign them or not so I wanted to look at the potential contracts they could sign and whether or not they are worth the new contract from the Yankees in my own opinion.

DJ Lemahieu signed with the Yankees before this past season for a 2yr/24 million dollar deal. We all know what happened last year as Lemahieu garnered multiple MVP votes and came through clutch time and time again for the Yankees. Not only did he come through at the plate, he willingly played all over the infield wherever the New York Yankees needed him. Normally a gold glove second baseman, he also played third base and first base to keep his bat in the lineup. He was the prototypical utility player for the Yankees. In the event that the 2020 season moves forward and Lemahieu is able to have a similar season to last year (albeit most likely a smaller sample size of games), I think the Yankees will absolutely look to re-sign him. His current contract would be a nice starting point and maybe he would be given a little bit of a raise or even a third year on his contract. All things said and done I think he settles in for a 3-year deal around 30-35 million per year. As a sign of good faith, the Yankees could also throw in a team option for a fourth.


Masahiro Tanaka came over to the U.S. with sky-high expectations to become New York’s ace of the rotation for years to come. While that didn’t quite pan out, there’s no question that Tanaka has more than held up his end of the contract he signed. He may not be an ace, but he is probably the most reliable pitcher they have had each year despite the partially torn UCL. His regular season stats don’t blow you away but the postseason is where Tanaka shines. With the UCL tear that could force him to have Tommy John surgery at any point in the future, he is definitely a gamble. Given all, we know about his ability to give the Yankees 160+ innings along with postseason dominance, and taking into account the potential health risk, I could see Tanaka signing somewhere in between the Twins Kyle Gibson’s 3yr/30 Million contract and the Braves Dallas Keuchel’s 3yr/55 million contract both signed in the previous offseason. Those two players represent players close in comparison to Tanaka in terms of age, statistical history, and health history. That would also put him playing into his age 36 seasons. If he gave them three more years at roughly 15 million average annual value I think he would be worth it. If the New York Yankees have to sweeten the deal they could throw in a team option for a fourth year. Tanaka seems to be someone who enjoys being a Yankee and would take pride in suiting up with them for the remainder of his career.

James Paxton came over in a trade last offseason for a former New York Yankees top prospect. He also had high expectations as someone who could help anchor the pitching staff with Luis Severino. The book on Paxton is simple: He has yet to remain healthy over a full season, but when he is, he can give you ace quality pitching outings. He put together a good stretch of games towards the end of last season, and also came up clutch against the Astros in the playoffs. For Paxton, he may be one of the few top tier pitchers on the market next offseason thus inflating the contract he signs. I think the contract he signs will be comparable to the one Hyun Jin Ryu signed this past offseason at 4 yr/80 million. Both pitchers have injury histories but are dominant when healthy. However, if he is the only top pitching commodity out there, expect that price to go higher with teams bidding against each other (i.e Zack Wheeler). As much as I’d like to see the Yankees re-sign Paxon, I think there will a more pitching needy team out there willing to give him more money than he is worth and will force the Yankees to let him walk.

Given the state of the sports world currently, it’s anyone’s guess when or if we will have a 2020 season. No matter what happens, the Yankees will have some tough decisions to make afterward.