Yankees Mailbag: Luxury tax, Didi Gregorius, team of the decade

Hello, everyone, and happy Friday! We have a small mailbag, but a good one I think. Remember to submit your questions in our weekly call, or by e-mail to pinstripealleyblog [at] gmail [dot] com. Thanks and enjoy.

Ruff Trade asks: Is there any chance that Hal would allow Cash to break into the third tier of luxury tax for one year? With Ellsbury and Happ, definitely and potentially off the team payroll for 2021, couldn’t the team take advantage of the elite pitching available this year?

Fun fact: The Yankees have a ton of money coming off the books following the 2020 season. Not only will they shed Jacoby Ellsbury’s contract, but they will probably make sure J.A. Happ’s option doesn’t vest. Masahiro Tanaka and DJ LeMahieu’s deals run out, too. After accounting for Ellsbury’s $5 million buyout, they’d have $68.1 million freed up. That kind of cash should let the Yankees push into the upper-boundaries of the luxury tax this year, then slide back down after 2020.

That said, the Yankees aren’t just worried about the financial implications. They have demonstrated an aversion to long-term contracts, preferring shorter pacts as a way of mitigating risk. The club may also not be comfortable with the draft-pick forfeiture at the third level, where teams fall back 10 picks upon entering this tier. We’ll have more on this at length early next month. Stay tuned!

Jason8291 asks: Which Yankees team was your favorite of the decade and which do you think was the best/most talented?

For favorite team, I’d have to go with 2017. It’s not particularly close either. I think everyone expected it to be a rebuilding season, and then the Bombers won 91 games. Aaron Judge crushed dingers left and right; Luis Severino had an ace-caliber campaign; plus the team finished one game shy of the World Series. I loved every single minute of that season.

As for the most talented? A fully healthy 2019 Yankees has to top the list. The 2010 squad also comes to mind. Maybe it’s recency bias, but I think the ‘19 Yanks could give any other year a run for its money.

SJComic asks: Now that Didi has no qualifying offer attached to him, do the Yankees make a lowball offer to him? Maybe like a prove-it deal, 1/12 or 2/24?

The Yankees didn’t extended Didi Gregorius a qualifying offer—valued at $17.8 million—but that doesn’t precluded them from signing the shortstop. They very well could ink him to a long-term deal, but one at a lower AAV.

What would it reasonably take to bring Sir Didi back? Consider some of the more reputable predictions.

Jim Bowden (subscription required): One year, $12.5 million
MLB Trade Rumors: Three years, $42 million
FanGraphs: Three years, $48 million

Bowden appears low on Gregorius, but MLB Trade Rumors and Kiley McDaniel might be on to something. How about splitting the difference and giving him the Carlos Beltran deal, three years and $45 million? I’d do that in a heartbeat.