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Yankees Mailbag: Supporting Gerrit Cole, playoffs and front office dynamics

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Check out the answers to the latest round of mailbag questions.

Division Series - New York Yankees v Tampa Bay Rays - Game One Photo by Sean M. Haffey/Getty Images

Good morning everyone, are you ready for another round of mailbag questions? Remember to send in your questions for our weekly call by e-mail to pinstripealleyblog [at] gmail [dot] com.

Ruff Trade asks: Shouldn’t the front office be doing more to support the signing of one Gerrit Cole? Isn’t it a waste to throw 324 million dollars at an ace and then stop? Re-signing Tanaka and/or Paxton could still happen, of course, but shouldn’t there be a stronger desire to pry loose a difference maker like Castillo? They already blew it with Carrasco. Kluber is a lottery ticket and not a sure thing and we don’t even know if that’s going to happen.

I understand the ‘narrative’ is that the Yanks lost the most money during 2020 but isn’t it short-sighted to look at one bad year (ok, maybe two, just maybe) and not at the positioning of the entire franchise?

I’d agree with that. While it seemed at the time that the Yankees signed Cole that they were an ace away, 2020 was definitely a learning lesson that they could just as easily be leaving him on an island in that rotation. It was fair to enter the year confident in having a brand-new ace to go alongside a young ace in the making with Severino, a reliable postseason starter in Tanaka and a high upside but injury-prone option in Paxton, but only Cole lived up to expectations among the four. That’s not really fair to Severino, who could still become a strong second if he recovers from injury, but it’s the reality of how things stand right now.

Expecting things to just flip back to the way they hoped it would go at the beginning of last year doesn’t seem too likely. Severino is months away from being ready to go, and Paxton and Tanaka aren’t even locks to return to the team. The second half of the question is the bigger indictment, in my opinion. That Yankees are the safest horse to bet on in North American sports, with only the Lakers or Cowboys in their stratosphere. They’ve gotten theirs for decades, and a year of running negative isn’t going to suddenly cripple Steinbrenner's wallets. Even if this year is a wash too, they’ll go right back to printing money before long. As Jake wrote earlier in the week, it’s really not that expensive to go all-in.

jjpf asks: Manfred recently fed the media the possibility of a 162 game regular season. With this number in mind, how many teams do you think will populate the 2021 postseason? Could you please answer: a) the number you would prefer; b) the number you think MLB will choose and; c) the structure the playoffs might take.

I think that Manfred will probably get a 12-team postseason secured for this season, whether that’s what they set out for or what they wind up compromising on. Teams accepted the 16-team bracket due to the shortened season and a need to account for the variance in not playing across divisions last year, but I think that format is way too much for a 162-game season. It may not be the last time we see it, but for the moment I think that format gets shelved.

What would be interesting in a 12-team format is how they handle the wild cards. Last season they introduced the concept of guaranteeing the top two teams in each division making the postseason, and I could see Manfred toying with that idea again. Personally I’d be against this, and I don’t have a clue if it would be popular league-wide, but I don’t think we see too much change so I’d bet on just adding the additional team per league.

From there MLB could adopt a postseason bracket just like the one the NFL had until this year, with the top two teams in each league getting a bye and the lower four teams playing in the Wild Card Round. They could choose to experiment here too by keeping the best-of-three format they debuted last season, but since there would only be one division winner and three wild card teams in this round it would ultimately be fairer to make it another best-of-five. Perhaps that leaves the top teams waiting around too long, but I think this would be the optimal format for 12 teams.

Steve F. asks: Interesting article on Cashman’s rigidity. Follow up question: how much of this is actually tied to the inflexibility of the budget he is given by ownership? IOW, it makes perfect sense that he can’t really move on any other medium sized deals until he knows the exact terms of (hopefully) a deal for DJ (same with Cole last year) because his bottom line budget is fixed.

This was in response to a piece that Peter wrote earlier this week. I’m not exactly sure if it was meant for the mailbag, but I figured this would be a decent place to respond. In case you haven’t read the article it refers to, you can check that out here.

I do agree that a large part of Cashman’s inflexibility revolves around Hal’s insistence on trimming the budget to avoid the repeater tax. However, that isn’t the sole factor for Cashman’s tendency to tread water over the years. Hal doesn’t have much — if any — say in the Yankees’ reluctance to include top prospects in trades. That’s a trademark of Cashman, and it’s something that he has to weigh. I’m not even talking about Jasson Dominguez either; Cashman has a history of trying to negotiate in quantity when the rest of the league values quality.

Of course, Cashman probably relies on this method because the Yankees don’t have many highly-ranked prospects — something that he can be directly critiqued for. Hal doesn’t have any involvement in the Yankees’ scouting and draft success — that falls on Cashman, and outside of international signings it’s been a very mixed bag of results. Naturally, the Yankees don’t have favorable draft positioning because they’ve been in contention constantly over the course of his career, but baseball is pretty unique in having lots of MLB-caliber players come from outside of the top rounds of the draft.

This would be far less of an important point if the Yankees flexed their most valuable asset more, and as we’ve covered Hal is unquestionably an obstacle there. But as much as we may wish it wasn’t that way, it is — and it probably isn’t changing any time soon. That means looking elsewhere for advantages, and that’s something that Cashman could arguably use some adjusting in.