New York Yankees Analysis: Is this the most important offseason in years, are the Yankees running out of time?

New York Yankees, Hal Steinbrenner

The New York Yankees are facing a most difficult and important offseason than they have since 2008. The only similarity is that the Yankees have now gone years without a World Series win. This past season saw the Yankees again have an early exit in the postseason—this time to the Tampa Bay Rays in the ALDS.  In the last four years, the Yankees couldn’t get it done in either the ALDS or ALCS.

What is different this year compared to 2008 is the New York Yankees have lost a tremendous amount of money this past season with no fans and associated revenue. According to Michael Kay, the Yankees lost more money than any team in baseball. But when you consider the Yankees’ many money streams, they also made more money than any other team. Averaging it out, the Yankees had a 40% loss overall. A 40% loss for lower-tier teams can be devastating. Not so much for the Yankees; they are far from broke.

“Our objective was to win a world championship. We failed in that endeavor,” owner Hal Steinbrenner told Michael Kay on ESPN New York 98.7 FM last month (via’s Bryan Hoch). “Does that mean the entire season was a failure? No. I don’t think winning 10 in a row was a failure, and last year, I don’t think winning (103) games was a failure. I know people disagree with me on that, but I look at the season as a whole.”

That statement also highlights another difference in the team. A change in ownership. With George M. Steinbrenner, it was “World Series or bust.” As you can see from the statement, new owner Hal Steinbrenner still wants to win, but he looks at the success or failure slightly differently.

After 2008 George and the company went out and signed CC Sabathia, A.J. Burnett, and Mark Teixeira for the sum of $400 million. The result of that purchase was a World Series win at the end of the season, the first since 2000. Hal Steinbrenner is not his father; he is a more conservative businessman; it is very doubtful he will spend anywhere near the $400 million his father did to solve the club’s problems. To be fair to Hal, he is in a different situation than his father was in 2008. In 2008 the team was flush with money and would be opening a brand new stadium.

The New York Yankees, for years, were known as a team with a lot of older veterans on the team. That all changed in the mid-2010s with a new core of “Baby Bombers,” including Aaron Judge, Gary Sanchez, Miguel Andujar, and Gleyber Torres. Those baby bombers are not so much babies anymore; outside of Andujar and Torres, the others are approaching 30 years old. Add to that Gerrit Cole, Giancarlo Stanton, Zack Britton, and Aroldis Chapman are all on the wrong side of 30. I bring this up because, with this core, the Yankees are running out of time to achieve that 28th World Championship without a complete overhaul.

What the Yankees must do to win another World Series

The Yankees had several significant contracts come off the books after the season, including Masahiro Tanaka – ($22.1 million per year), Jacoby Ellsbury – ($21.9 million per year), J.A. Happ ($17 million), James Paxton – ($12.5 million), and DJ LeMahieu – ($12 million), Brett Gardner – ($10 million). Ellsbury did still count against their luxury tax payroll. Now that his contract is expired, he’s completely off the books. That gives the Yankees $95.5 million to spend. Last year’s normal payroll would have been $257,409,316, which is well over the $210 million luxury tax threshold that Steinbrenner says he wants to stay under.

The Yankees want to save with the $47 million that leaves only something less than $48 million available to fix everything they want to fix. As announced, DJ LeMahieu will be a priority signing, that will likely cost the Yankees $20 million; if they accomplish that, they will have just $28 million to hire a new premium type pitcher, solve the Yankees catching problem and address the situation at shortstop, they may also wish to bolster the bullpen after losing Tommy Kahnle to Tommy John surgery. $28 million doesn’t seem to solve everything. Cashman is going to have to be very creative.

If general manager Brian Cashman and, more importantly, Hal Steinbrenner really want to win their first World Series in twelve years, it appears they are going to have to break the bank. The Yankees so far have made no moves, but it is still very early in the offseason. Time will tell if they want to balance the books or become champions again.