5 questions left unanswered by Brian Cashman, Aaron Boone and Hal Steinbrenner

4. Will Masahiro Tanaka Be Back With the Yankees?

Yankees starting pitching Masahiro Tanaka is about to become a free agent.

Masahiro Tanaka will be a free agent for the first time in his MLB career after spending the last seven years in the Bronx. He decided to opt into his contract after the 2017 season and spend an additional three years with the team instead of exploring the open market.

His final season in pinstripes didn’t entirely go well, but fans want him back. He provides stability in the middle of the rotation and is a reliable postseason arm, despite his two bad outings against the Indians (thanks to MLB botching the weather delay) and Rays.

Boone and Cashman had great things to say about the right-hander, but wouldn’t comment about his future with the team beyond 2020.

If Tanaka’s Yankees career ended in two weeks, he will have finished 78-46 with a 3.74 ERA, 1.13 WHIP and 991 strikeouts in 174 games (173 starts). His postseason numbers include a 5-4 record with a 3.33 ERA, 0.98 WHIP and 44 strikeouts in 10 starts.

Given that James Paxton is a free agent as well, it’s hard to believe Tanaka won’t be back with the Yankees because the one thing they need is more starting pitching behind Gerrit Cole. Though one could argue they need a lefty, we don’t think Cashman will invest millions in the oft-injured Paxton.

3. Is Gleyber Torres the Shortstop of the Future?

Yankees shortstop Gleyber Torres was not great at defense this year.

We’ve heard the Francisco Lindor trade rumors. We heard those who want Didi Gregorius back. What’s next? Hopping in a time machine to bring back prime Derek Jeter?

It’s no secret the Yankees’ infield situation is a bit complicated at the moment because Gleyber Torres far from made a seamless transition to shortstop. On top of that, you’d think they have to re-sign DJ LeMahieu given his performance over the last two years, which means Torres will have to be the shortstop in 2021.

But is he the shortstop of the future? We do not have an answer to that either!

Cashman said Torres is “currently our shortstop” but the team will discuss with “all parties involved” if there’s a better way to go. We’re scared to even know what that is. Moving him back to second and letting LeMahieu hit free agency to bring in a big-name shortstop? Keeping Torres there for 2021 and seeing if it works out over the course of a full season? Trading Torres in a deal for Lindor and keeping DJLM at second?

Sorry guys, but this is what happens when you don’t have a definitive answer. You’re forced to scramble and consider any and all possibilities because of how unpredictable the offseason can be. And the fact of the matter is that the Yankees could go a number of ways to improve or shift around their infield. Or they can keep it the same.

Cashman’s answer provides no insight for any of that, however.

2. Does Gary Sanchez Have a Future With This Team?

The Yankees gave conflicting responses on Gary Sanchez.

Gary Sanchez has yet to play in more than 122 games in a single MLB season. He’s batted .200 since the start of 2018. His defense has hardly improved (it’s still bad). He was benched in favor of Kyle Higashioka for a majority of the 2020 postseason. Fans have expressed their discontent with him, to put it nicely.

However, Boone and Steinbrenner were optimistic about Sanchez’s prospects in 2021. They believe he’s yet to reach his ceiling and can still contribute in a big way to this lineup.

Cashman? Not so much, it seems. Here are his thoughts on the matter.

So with those conflicting responses, what does that tell us? Will Sanchez simply be platooning with Higashioka? Will he be traded? The man was booed in spring training this year, so a trade could very well be on the way given how drastically he’s fallen out of favor with the fanbase.

But the Yankees are not ones to do business in that manner. They’d likely be hard-pressed to deal Sanchez when his value is near rock bottom only to watch him rake for another team. Then again, Sanchez is another redundant player in this lineup. He hits home runs (though they’re usually not timely), he doesn’t hit for average, and he strikes out a ton.

So, to answer your question, we still don’t know what will happen with El Gary.

1. Will the Yankees Spend in Free Agency?

The Yankees have issues and might need to sign some free agents.

There aren’t a ton of available free agents this offseason that will help improve the Yankees’ roster, but there are some, and they won’t entirely come cheap. Michael Brantley and Tommy La Stella could be intriguing additions. Perhaps another reliever or two (Liam Hendriks and Blake Treinen) could help? Maybe a star pitcher in Trevor Bauer?

The first order of business is taking care of their own impending free agents, however, which include LeMahieu, Tanaka and Paxton, while Brett Gardner has a team option on his deal. So what’s going to happen?

Steinbrenner told reporters that the Yankees probably sustained the biggest financial losses of any organization due to the global pandemic, and that doesn’t bode well for spending considering this rendition of the Steinbrenner regime has exercised fiscal caution more times than fans would prefer. The days of George handing out blank checks are gone (with the exception of Gerrit Cole, because that needed to happen).

And forget about spending in free agency in terms of players outside the organization! Will they even spend to keep their own guys? LeMahieu, Tanaka and Paxton won’t exactly be cheap either.

There’s still a lot of uncertainty surrounding 2021. Will fans be permitted back at games? Will we need a vaccine to get enough attendance for organizations to feel comfortable spending big money again?

We don’t know, and it seems the Yankees don’t either. There’s never been this much uncertainty surrounding a perennial World Series contender.

Yankees: This Whit Merrifield trade with Royals could actually work

The New York Yankees should import the do-everything bat of Whit Merrifield in a trade with the Kansas City Royals this offseason.