Brian Cashman needs to spend big this winter with 2021 strike looming

With the possibility of a strike looming following the 2021 season, the Yankees need to go all-in to win the World Series next season.

For the 11th straight season, the New York Yankees failed to win a World Series. It’s becoming an all-to-familiar annual ending for the Bronx Bombers.

With hopes high even in a shortened 60-game season, the Yankees once again dealt with injuries and underperforming players. With a roster this talented, that shouldn’t matter, but here we are again.

And with several key Yankees hitting free agency this winter, general manager Brian Cashman has his work cut out for him to avoid another frustrating ending to 2021.

Starting pitchers Masahiro Tanaka, J.A. Happ and James Paxton are free agents. Setup reliever Zack Britton could also become a free agent if the Yankees decline his 2022 contract option. Outfielder, and the longest-tenured Yankee, Brett Gardner could be a free agent if the Yankees reject his team option.

But most important of all? DJ LeMahieu will be up for grabs.

After 11 years of frustration and with the possibility that there will be a work stoppage in 2022 after the CBA expires following next season, it might be time for Hal Steinbrenner to allow Cashman to open up the checkbook and spend bigger than ever before. No, not just one splash in free agency like last year when they inked Gerrit Cole to a nine-year, $324 million contract — it’s time to unload and add whatever we need regardless of the price.

There’s a real possibility that the Yankees are going to lose at least two of their free-agent starting pitchers. Luis Severino will be returning next season at some point from Tommy John Surgery and Domingo German will be back from his suspension, but it’s unclear how effective either of them will be after long layoffs.

While those have the possibility of being nice re-additions, Cashman and the Yankees need to make a run at Trevor Bauer. If he wants a one-year deal, great. If he wants a five-year deal, make it happen. Whatever it takes.

It might also be time for the Yankees to move on from Gary Sanchez. He’s oft-injured and has been a disappointment on both sides of the ball in a big way since the start of 2018. The Yankees can no longer continue waiting around for this to not be the case.

We truly don’t know what Sanchez could bring back to the Yankees in a trade, but the Yankees need to make a serious run at J.T. Realmuto. Pay the man. He’s a tremendous defender, provides a threatening bat, and would add another veteran voice to the Yankees’ clubhouse.

While we’re mostly focusing on big spending at the moment with these moves, we must address that Cashman still needs to pepper in one or two of his shrewd trades that bolster the roster in some capacity, whether big or small. It’s time for the GM to empty the clip and ensure this team is ready to contend for 2021 and well beyond.

Eleven years is 11 years too long in between championships for the Yankees. We’re likely staring down the barrel of a work stoppage after 2021, and the Yankees cannot take a chance with having an incomplete roster heading into next offseason. The time is now. The front office and ownership will be glad they took action now instead of grappling with even more uncertainty later.