Five moves the Yankees should make this offseason after failing to reach the World Series

The Yankees' quest for their 28th World Series title will have to wait yet another year after being eliminated by the Astros in the ALCS for the second time in the past three seasons. The pressure to return to the promised land continues to mount in New York. 

It has been 10 years since we last saw the Bronx Bombers in the Fall Classic. For most teams, that's not too lengthy of an absence. For the Yankees, however, this is uncharted territory. The 2010s are the first calendar decade without a World Series appearance for the Yankees since the live ball era.

GM Brian Cashman was criticized this past trade deadline for not being aggressive on the market and addressing New York's starting pitching needs. In hindsight, much of that criticism was deserved considering the the starters' inability to pitch deep into games became an issue against Houston. 

For Cashman and the New York front office, the clock is ticking heading into the 2020 season.

With that being said, desperate times call for desperate measures, and below you'll find my five moves the Yankees should make to get back to the World Series. 

1. Sign a starter that can pitch deep into games

Simply signing a starter is not enough. They need to land a front-line arm that can pitch deep into ball games. 

The starting staff ranked 15th in ERA (4.51) and 26th in innings pitched (778 1/3) during the regular season. As for the postseason, Masahiro Tanaka and James Paxton were the only two starters to even sniff the sixth inning. Having a starter with the ability to take over a ballgame for a full nine innings might be the missing link. A healthy Luis Severino is also crucial for their success.

Gerrit Cole, Madison Bumgarner, Zack Wheeler and Stephen Strasburg (player-option) are all among the high-priced veteran arms on the market with the ability to pitch deep into games. Cashman needs to land one of the four names above.

2. Trade Sanchez

Sanchez might have been booed in Yankee Stadium more than the opposing players this postseason.

The power-hitting catcher is a threat in a lineup already stacked with plenty of power. He is a luxury, not a necessity. 

Sanchez has a total of just 10 hits since Sept. 1, including a .129 batting average in the postseason. He has spent much of his four-year career on the IL and has been criticized for lack of hustle on multiple occasions. In today's game, a power hitting catcher is simply not needed, especially in the American League (the tandem of Martin Maldonado and Robinson Chirinos out in Houston is a great example). Austin Romine has proven he is more than capable of managing the staff.

Sanchez is due for arbitration this year and is not set to hit free agency until 2023. There are a handful of teams who would be enticed by a catcher who provides some pop in their lineup (i.e. White Sox, Padres, Braves); all would likely offer up a nice haul to acquire him.

3. Sign a veteran catcher; re-sign Romine

Assuming they deal away Sanchez, re-signing Romine should be the next task. Romine had a career year in 2019, slashing a career high .281/.310/.439 in 72 games. Most importantly, he has one of the more respected baseball minds and has often been highly touted for his ability to connect with his pitchers.

"Plain and simple, Romine just calls a great game," said one Yankee insider via The New York Daily News. "The pitchers love him."

Once that is squared away, Romine will need a platoon partner. Luckily, there is a long list of veteran squatters who fit the bill

Matt Wieters, Francisco Cervelli, Stephen Vogt and Alex Avila are set to hit free agency this winter -- any of those guys would be great fits in New York.

4. Let Encarnacion walk in free agency

Much like Sanchez, the parrot man is a luxury, not a necessity in the already powerful Yankee lineup. 

Encarnacion has a $20-million club option for 2020, and New York should decline that option. The logjam in the outfield is a direct result of a logjam at the DH spot due to Encarnacion. If Giancarlo Stanton can get healthy and take back his DH position, New York can then give the much deserved at-bats to Clint Frazier or Mike Tauchman.

Depth is crucial in a grueling 162-game grind, but the Yanks are already built to withstand the marathon without Encarnacion. 

5. Trade for Syndergaard and Diaz

In a perfect world, this move would kill two birds with one stone (trade Gary Sanchez away and grab a starter who can pitch deep into games). Of course, MLB front offices are anything but a perfect world so we will try to stay realistic.

The Mets have historically been reluctant to deal with their crosstown rivals. However, they are on a search for a new skipper and many of their players could use a change of scenery -- including Syndergaard and Diaz. As much as they want to deny it, a rebuild could be in the cards.

This also means they would be a perfect trade partner for the Yankees. 

Cashman has prospects to toy with (i.e. Frazier, Deivi Garcia, Jasson Dominguez) and they should all be on the table this winter. 

Would a package of Sanchez, Frazier, Garcia and Dominguez would be enough to entice Mets GM Brodie Van Wagenen in negotiations? Bringing in Sanchez and Frazier would also be a way to convince Mets fans that it is not a complete rebuild.

Imagine this starting rotation:

  1. Noah Syndergaard
  2. Luis Severino
  3. James Paxton
  4. Masahiro Tanaka
  5. J.A. Happ

It's going to be an intriguing winter in the Bronx. Aggressive offseason moves have rewarded both the Red Sox and Astros with World Series championships. If New York wants to find its way back to the World Series, the same approach might be the formula for ring No. 28.

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