When Yankees will likely strike in tricky MLB free agency

It has been close to three weeks since the Yankees’ last transaction. That is when they picked up a $14 million club option for 2022 on lefty reliever Zack Britton.

Based on a strong field of players being non-tendered by Dec. 2 due to COVID-19 costing clubs gobs of money, it might be about the same time or longer before the Yankees or other clubs make another move.

A person heavily involved in the situation predicted there will be free agent signings before Dec. 2 but estimated the number might be in the single digits.

The Yankees have two very important players on the free agent market they would like to retain, and there is a chance DJ LeMahieu and Masahiro Tanaka return to The Bronx. However, in 2020, there is no such thing as a lock in any walk of life, in a world that is constantly throwing up COVID-related roadblocks.

The Yankees have a decision to make concerning Gary Sanchez, who will turn 28 on Dec. 2 and is a candidate to be non-tendered after a miserable 2020, in which the two-time All-Star batted a baffling .147 and struck out an alarming 64 times in 156 at-bats while being paid $5 million.

The business is in the dancing process when it comes to high-end players such as Trevor Bauer, J.T. Realmuto and LeMahieu. Teams contact the players representatives and show interest, but according to people on each side of the table, the biggest free agent deals don’t get done before December is about to turn into January.

An exception to that was Gerrit Cole and the Yankees agreeing to a nine-year deal worth $324 million in the second week of December, during last year’s winter meetings in San Diego.

Spring training camps had already opened in February 2019 when Bryce Harper signed a 13-year deal for $330 million with the Phillies and Manny Machado and the Padres entered into a 10-year contract for $300 million.

That was the same year LeMahieu had to wait until Jan. 4 to sign a two-year contract for $24 million with the Yankees. Considering his sensational two years in pinstripes, the 32-year-old infielder, who led the majors with a .364 batting average and 1.011 OPS and finished third in the AL MVP race, is in for a substantial raise.

As they did with Derek Jeter following the 2010 season, the Yankees could tell LeMahieu to shop and see what is out there before offering him a deal. Ditto for Tanaka.

Should the Yankees want to get under the $210 million luxury threshold for 2021, bringing back LeMahieu and Tanaka might be it for big-name signings. Even then, they might have to see if another team would take right-handed reliever Adam Ottavino and his $9 million salary, or part of it, for 2021 in a deal.

The Yankees had until three days following the World Series to pick up Britton’s $14 million option for 2022, and they did that. If they hadn’t, Britton could have opted out of the $13 million he is due for 2021 and would have become a free agent.

“Very excited to continue the pursuit of a championship with the Yankees,” Britton tweeted about his return on Oct. 29.

Getting LeMahieu and Tanaka back would greatly enhance the Yankees’ chances of winning their first World Series title since 2009. But don’t count on that happening, at least until after Dec. 2 and maybe a lot longer.

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