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Five tough questions facing the Yankees this offseason

After a disastrous season, the Yankees need to decide on the direction this team will take going forward.

MLB: Wildcard-New York Yankees at Boston Red Sox Bob DeChiara-USA TODAY Sports

Well, that was a disappointing end to one of the most disappointing Yankees seasons in recent memory. Coming into the 2021 campaign with lofty expectations from fans and analysts alike, the Bronx Bombers failed to realize their World Series aspirations. Now, the team looks as though it is on the brink of a transitional period that could potentially lead to an overhaul of its current roster.

Here are some of the most pressing questions facing this team as they enter the offseason:

Will Hal truly open the bank?

MLB: New York Yankees-Workouts Kim Klement-USA TODAY Sports

This is the question on the minds of Yankees fans everywhere. In recent years, the Yankees front office have handcuffed themselves, in part, by forcing themselves to adhere to a strict luxury tax cap. This has led Brian Cashman and his team look to fill obvious roster holes with cost-effective “solutions” as if they’re the Tampa Bay Rays. Gerrit Cole’s monster contract was the exception rather than the rule.

The problem with this strategy is that the Yankees are not the Rays; they are the second most valuable sports franchise in North America. Currently valued at $5.25 billion, there is simply no excuse for this team’s penny-pinching ways of late. After such a disappointing run, is this finally the season that Hal Steinbrenner wakes up and realizes that their offseason spending strategy should rival the Los Angeles Dodgers’ approach?

Who is managing this team?

MLB: New York Yankees at Toronto Blue Jays Dan Hamilton-USA TODAY Sports

One thing is certain after this season: Aaron Boone has proven that he is incapable of managing this team to long-term success. The question remains, though: Who will be managing this team next year?

On one hand, Boone’s contract is up, and I haven’t seen any rumblings about contract extension talks. On the other hand, Steinbrenner and Cashman very publicly backed him earlier this year and the word from the media is that he’s always worked closely with the front office. Has the organization seen enough to move on from him, or do they feel like he is still the right man for the job? And, perhaps more importantly, is there a better candidate to replace him?

Who is this team’s first baseman?

MLB: Tampa Bay Rays at New York Yankees Wendell Cruz-USA TODAY Sports

Luke Voit only managed to appear in 68 games due to a combination of injuries and what appears to be an ill-timed benching. When he played, he slashed .239/.328/.437 with 11 home runs and a 111 wRC+, a far cry from his stats in 2019 and 2020.

At the deadline, the Yankees somewhat unexpectedly traded for Anthony Rizzo. Although he was a definite defensive upgrade over Voit, he only managed to slash .249/.340/.428 and a 113 wRC+. While that’s not a terrible line by any means, the Statcast data paints a portrait of a once-elite hitter in the early stages of what may be a sharp decline: Rizzo doesn’t barrel the ball, he doesn’t hit it hard, and his whiff rate is creeping up year-over-year.

So, who is the answer at first base? Rizzo is a free agent on the wrong side of 30 showing serious signs of decline. Voit, unfortunately, can’t seem to stay on the field. Freddie Freeman is a free agent, but as I mentioned earlier, the Yankees seem to be in money-saving mode for some reason and it’s unclear if Freeman even leaves Atlanta. C.J. Cron just signed an extension with the Colorado Rockies. There isn’t a player currently in the organization ready to be counted on. Should I continue, or do you get the picture?

Who is this team’s shortstop?

MLB: New York Yankees at Boston Red Sox Winslow Townson-USA TODAY Sports

After a remarkably bad stretch from Gleyber Torres at short, the organization mercifully moved him back to second base. But, going forward, who is the answer? This, perhaps, is even more of a question than the murky catcher position, where there are far fewer legitimate solutions on the open market.

This free agent class at shortstop is absolutely loaded, with Carlos Correa, Corey Seager, Trevor Story, Marcus Semien, and Javier Báez all set to earn massive paydays. Again, though, the team’s frugality might jeopardize their chances at signing any of those names, even though someone like Seager is tailor-made for this Yankees team.

Within the organization, both Anthony Volpe and Oswald Peraza project to have bright futures, but neither are quite MLB-ready just yet. There are stopgap options available in the likes of Andrelton Simmons and Freddy Galvis, but are the Yankees in a position to punt production from arguably the most important position on the diamond for a couple years and hope that Volpe and Peraza pan out?

Will this organization sign Aaron Judge to a lengthy and expensive extension?

MLB: Tampa Bay Rays at New York Yankees Wendell Cruz-USA TODAY Sports

Aaron Judge just put up a truly remarkable season. I can’t believe I’m asking this question, but will the Yankees finally extend him? He affirmed just last night that he wants to spend his career in pinstripes.

I understand that there are past injury concerns, but in this market, Judge is absolutely the type of player who an organization should lock up long-term. From a business perspective, he’s probably in the top-five most easily marketable players in the league right now. From an on-field perspective, he appears to be the de facto leader of the team and his on-field production matches that status. From a fan perspective, he is the face of this organization and one of the most popular players in Major League Baseball. The answer should be yes, the Yankees should extend him, but will they actually do it? We’ll have to wait and see.

After a season marred by disappointment, poor performance, and downright stupidity, this offseason is shaping up to be the biggest that the organization has faced in quite some time. In fact, this offseason might be more entertaining than the season we just had to sit through, because lord knows that wasn’t exactly enjoyable.