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Yankees Mailbag: Offseason strategy, Freeman negotiations, and regrettable misses

The mailbag pushes into December with more and more concerns to address.

Oakland Athletics v Seattle Mariners Photo by Alika Jenner/Getty Images

Good afternoon everyone, it’s time for another edition of the mailbag. From here on out, the mailbag will be running every two weeks, due to a slower amount of information trickling in and a lack of action going on. Without further ado, let’s open up the mailbag for more of your Yankees questions. Remember to send in your questions for our (bi)weekly call by e-mail to pinstripealleyblog [at] gmail [dot] com.

Stephen M. asks: I can’t remember when the hot stove was this active and the Yankees weren’t a part of any of it, especially when the fans are clamoring for reinforcements. With top profile players all getting long-term contracts elsewhere, do you think the Yankee strategy is more aligned to go the trade route instead of free agent deals?

If it isn’t at this point, than I think the Yankees have made a grave mistake in navigating this offseason. As it is, I think that they’ve made highly questionable decisions in not being even remotely involved in the bidding for so many of the names that’ve come off the board already. It’s difficult to say what the budget looks like with the luxury tax squarely in the line of sight during these CBA discussions, but the Yankees have looked more pretender than contender of late and need a jolt to jump back to the top of the AL. Intentionally not going for any of the significant additions that were available seems damning, regardless of the price tag.

There are good trades that the team can make to achieve solid improvement. Matt Olson and Luis Castillo stand out as two of the most obvious names that are available, but there are plenty of deals that could net the Yankees wins upfront. The question becomes who do they part with to make these deals though, and we’re once again seeing that the Yankees have a small pool of untouchable prospects like Jasson Dominguez and Anthony Volpe. Whether or not they’re right to hold onto those players is a separate question, but getting teams to part with valuable major league talent without parting with your own top-tier prospects is a tough challenge to accomplish, especially when so many comparable players are available for just cash.

Larry S. asks: Do you think the Yankees would give Freddie Freeman the six year contract he wants? Atlanta seems to be dragging his negotiation.

I think the Yankees would and should offer that contract, but it might specifically be the contract he’s seeking from Atlanta, not just in general. If the tax to pry him away from his preferred destination was, say, another year on top of that, it becomes an interesting question — one that we actually had a few days ago in the PSA Slack. The general consensus is that we’d be comfortable doing so, but it wouldn’t be such a sure thing — you’re likely to be tacking on a year that ends up being not so worth it.

Still, the overall contract would be worth pursuing. Freeman is an elite talent and appears to be aging gracefully as he approaches his mid-30s, far more Votto-like than Pujols-like. The bulk of Freeman’s eventual contract is most likely going to be highly competitive for the team that signs him, so if the cost is stretching him out a bit beyond his prime then out of any other context it would be a valuable signing. The risk for the Yankees comes in locking down a first baseman for so long when several key parts of their roster may end up needing to slide into a less demanding defensive position to maintain playing time down the road.

Psycho Bred asks: Who is the free agent that signed elsewhere that the Yankees should’ve signed, and why?

In terms of their needs and who they were originally reported to be interested in, I would say Corey Seager. Shortstop is the need of this offseason, and though there are still others available, based on the deals given out so far none of them are going to come cheap. Seager is one of the two top names that were on the market, and while he got one of the biggest contracts in free agent history it isn’t unreasonable to say it’s a worthwhile investment. Seager is just 28-years-old, and earned a contract that seems in line with the going rate for a young superstar infielder on the market. The Yankees could pivot to Carlos Correa, but if that contract was too rich for their blood there’s little hope they’ll get Correa for cheaper.

In terms of what got handed out though, I think the most stunning deal has been Max Scherzer’s three-year pact with the Mets. Without context it might be risky to bid $43.3 million per year to a player approaching 38-years-old when he’ll first put on the uniform, but Scherzer has been as solid a bet as you could make for most of the last decade. That he signed with a team in the same city as the Yankees only confirms that the West Coast preference was an in-season concern, and no longer much of a factor. Cold hard cash was the deciding factor, and the Mets were the ones willing to dish that out instead of the Yankees. It wound up being a major mistake to pass on Scherzer the last time he was a free agent, and it may have been a mistake to do so again this time.