‘His belief is you run to a problem’: A Yankees front office insider explains why Brian Cashman is better as his job than many outside the game believe

There is a disconnect between how Brian Cashman is viewed within the game, where he is considered an elite head of baseball operations, and on social media, where, well, generally he is portrayed as an incompetent nincompoop.

Of course, social media is where subtlety and nuance go to die.

Cashman is celebrating his 25th anniversary as Yankees GM this year and he is as polarizing as ever.

The subject of his ability is akin to arguing pretty much about any charged political issue — if a person comes with the opposite viewpoint, no amount of logic or facts will change that opinion.

I know this because I believe I hold the Yankees to a pretty high standard, but on those occasions when I read emails and/or social media (and I try to limit it for my mental well-being), I realize that you either have absolutism — every word in every column blames Cashman for everything from Josh Donaldson to climate change — or else you are in cahoots with the general manager.

Just for the record, my theory of covering a team as good as the Yankees are every year is to treat them like an “A” student, Thus, one element is to scrutinize what would keep them from winning 95 games and/or a championship (essentially what would keep them from continuing to be an “A” student). It is the standard the Mets are rising to now under Steve Cohen. Bad teams, in general, make me look for what might go well. Good teams make me look for what might go poorly.

Anyway, if you read me (thank you), you know that I do not think Cashman is a flawless GM. I feel like I have written too much over the years, for example, how right-handed he allowed the lineup to become and how much the Yankees ignored defense (until they didn’t). I was against the Joey Gallo trade on Day 1 and started railing about Isiah Kiner-Falefa at shortstop pretty early last season. And, well, I will stop there. This is the problem. I feel like I am defending myself. Which I don’t want to do. And I am doing it against an entity that is not going to accept the case anyway.

Especially since in the bigger picture, I actually do think that Cashman does a terrific job (I just ducked).

His teams have played a total of 17 games in which they were eliminated in his 25 seasons — never more than five in any one season. So he has never put a dud on the field. Twenty-one of his teams have made the playoffs. You want to point out the high payrolls he works with? Yep, huge advantage. But lots of other teams with huge payrolls have endured dips of non-contention.

I know there has been just one championship since 2001. But the Dodgers have won one since 1988, and that came in a pandemic-shortened, 60-game 2020. And if you told me I could hire one baseball executive today to run my team, I would pick Dodgers president of baseball operations Andrew Friedman. I think he is great at his job. But championships are hard to win, and in Los Angeles, he is regularly treated like an incompetent nincompoop.

Who would I pick second? Probably Theo Epstein. And I think Epstein is a Hall of Famer. I want to repeat that — I think he is a Hall of Fame executive. But he also has the debacle contracts of Carl Crawford and Jason Heyward on his ledger, really never did well in drafting pitching and left the Red Sox and then the Cubs at moments when both looked as if they were going to have to endure rebuilds of some form.

It is a reminder that there are no perfect heads of baseball operations. Only in various corners of cyberspace and on sports talk radio does anyone get all the decisions correct. In the real world, if you get 50 or 60 percent of the decisions right, you are doing great. And if you run a big-market team that spends, then your misses are really going to resonate on the Jacoby Ellsbury/Gallo level.

Does this mean Cashman should have the job for life? Of course not. Like everyone in the sport, he needs to be judged by his work. And, maybe, all the trades since the July 2021 deadline — many of which have not worked out well, to date — are a sign that his front office is losing its touch. Or maybe Jasson Dominguez/Oswald Peraza/Anthony Volpe are about to form the cornerstone, with Aaron Judge, of a long-term, high-level contender.

It will probably take more patience to determine this one way or the other than — for example — calling Cashman an idiot in August after trading Jordan Montgomery for an injured player, or a visionary in October for acquiring Harrison Bader.

This brings us to Jean Afterman. She is the Yankees senior vice president and assistant GM, the latter of which she became in 2001.

Asking her for an opinion of Cashman and how he is viewed is, of course, biased. It is her boss. Her friend.

But Afterman is someone I’ve long turned to for level-headed analysis of situations involving both the Yankees and the sport. She is an advocate, but one I always think provides logic and intelligence rather than spin. In this way, she reminds me so much of the late former head of the Players Association, Michael Weiner.

I can’t tell you how many times I called up Weiner and told him I was thinking about writing A-B-C and he would offer some version of, “Take me through your argument.” By the end — through his overwhelming control of information and supreme ability to see things in multi-dimensions and convey that vision — I was writing X-Y-Z. Afterman offers the same type of insight — the ability to add subtlety and nuance to the picture of why decisions are made or a process is followed, etc.

So I basically asked this week if it annoys her that her boss, Cashman, is viewed as incompetent by this large segment of vociferous fans. What follows is a conversation that is edited lightly in places for clarity:

Joel Sherman: Does it bother you that in the social media space Cashman is largely criticized (and worse) for his job performance?

Jean Afterman: “Absolutely. Nobody’s ever peeled back the curtain to see exactly what it takes to put a championship team on the field — what I call the mundane business of baseball. The day in and day out struggle with injuries, out of options, waivers. It is a long, grueling season. It’s 365 days a year, 24/7. [Cashman] gets no days off. I mean, no days, no time off, just a single-minded focus and trying to do this. If you compare him to all the other GMs out there, nobody has his track record. And it bothers me because if Oz were actually the Wizard in the Wizard of Oz, and you peeled back the curtain, that would be Brian, the actual wizard, not the fake wizard. And everyone thinks he is the fake wizard. And that bothers me.”

JS: Why do you think this criticism exists?

JA: “You know the world is flooded with people who think they know how the job is done, who think they can do it better and who think that you guys (reporters) don’t get it right. I don’t think people understand everything that goes into the job. It’s a little bit like criticizing a chessmaster when you don’t know how to play chess. Because why did he or she make that move? Right? Like, that’s the dumbest move in the world and they end up in checkmate in five moves.”

JS: What do you think outsiders generally don’t get?

JA: “When you get up in the morning and you’re making your coffee, you have one decision, which is push the button, make the coffee. If making the coffee were a decision that a general manager of the Yankees has to make, there would be 25 things that he would have to think about before he pushes the button to make the coffee. People online who are criticizing, who are howling for his head, they’re making the decision to push the button. That’s it. It’s an easy decision, but you don’t see the 25 other things that go into that decision. That’s what happens for every single decision that he makes. There are 25 to 30 data points, or more, that have to be considered. There’s also a lot more information that, if you are a fan, you wouldn’t have. Nobody wants to see how a sausage is made; they just enjoy the sausage. There are so many things that have to be considered in every single decision he makes. Also, we live in a lazy society. People don’t want to go look back and review his entire history. We live in an era of immediate gratification. Right now, unfortunately, the immediate gratification is to criticize and boo. They booed the freaking MVP (Aaron Judge in the playoffs). I mean, the MVP, who did something nobody had done for 60 years. So now instant gratification is booing. That’s the world we live in. People are looking at one decision in isolation. It’s crazy. It’s crazy.”

JS: What do you think are Cashman’s strengths?

JA: “I think his strength is consistency. I think his strength is that he keeps a very even keel. I think his strength is longevity. I think his greatest strength is that he is extraordinarily passionate and loyal to the Yankees. He believes in the Yankees and everything they do. He’s been very loyal to the Steinbrenner family and, in return, the Steinbrenner family has been very loyal to him. He’s extraordinarily loyal to the people who work for him. If somebody criticizes the signing of a free agent, he will respond to that. If somebody criticizes someone who works for him, he is guns blazing. … His belief is you run to a problem — do the stuff you don’t want to do first. Don’t procrastinate on it. If there’s a problem, he’s going to dash to it. He’s not gonna let it simmer, he’s not gonna let it sit, he’s not going to avoid it.

“If there’s an issue with a player, a problem with a player, instead of delegating it to somebody else, instead of avoiding the player, instead of not speaking to them, he will go directly to the player. We train our players that if you’ve had a good game or a bad game, you face the media, you face the fans, you don’t run from it. You have never seen Brian duck the phone calls and avoid you guys. If something goes on with us, he addresses it immediately. He’s not somebody that ducks.”

JS: What is Cashman’s weakness?

JA: “Everybody has strengths and weaknesses. I can give you some kind of pablum that his weakness is he cares too much. I think that after 25 years, whatever strengths he has are self-evident and whatever weaknesses he has, he has. He’s human. I don’t want to sound like I am hero-worshiping. But I have worked for him for over 20 years. And I wouldn’t work for him for over 20 years if I didn’t think the world of him — if I didn’t respect him, if I didn’t admire him, if I didn’t think he was the best. At this point of my life, I don’t need this job. I probably didn’t need it 20 years ago. But working with him has been incredible. The highs and the lows. … Sometimes the disasters and catastrophes are a lot more interesting than the hugging and fist bumping.

“He will always protect the reputation of the player. He’ll take the hit, so the player doesn’t take the hit. … He knows it is part of the job. That’s the other thing. He doesn’t bitch and moan about the negative press; it’s part of the job. He believes that when you sign up for this job, you sign up for the bitter and the sweet.”

JS: Do you think Cashman is bothered by the criticism?

JA: “I think it always bothers somebody; if you didn’t care you shouldn’t have this job. So I think it bothers anyone if you’re human, but at this point I would hope that if he walked away today, he would be able to sleep at night and be proud of his legacy. I think he always feels there’s unfinished business, and that’s a World Series. He should be in Cooperstown. He will be in Cooperstown. He is one of the greatest general managers of all sports. You look at what his peers say about him. Stephen Sondheim’s “Follies” has a great song. This old actress at the end of the first act brings the house down. She does this song all about that I am still here. He’s still here.”

JS: What is your response to the argument that Cashman keeps Aaron Boone around as manager because Boone is his puppet and that baseball operations makes all the moves?

JA: “One hundred percent untrue. There are some clubs where the manager will say, you know, basically, a trained dog could do what I do, because I’m just handed what I’m supposed to do. That’s where everybody goes (in their criticism) … It is disrespectful, and it is disrespectful to Boonie. He is an incredibly smart manager. … He understands the clubhouse. He understands the game. He’s a talented guy, and to say that somebody is pulling the strings, that’s ridiculous. And Brian’s never been like that. In any decision, he’s never enforced what he believes. There are clubs where that is true. It is not true here.”

JS: What is your response to the contention that the analytics department dominates all decision making?

JA: “That one always cracks me up because everybody … says, ‘analytics’, and that’s become a buzzword for something that isn’t actually there. The real thing is predictive analytics. You have all this data and you try and predict, because when you sign somebody you want to predict how they’re going to perform. You want to predict how a roster is going to perform. It’s all about trying to predict the future, which is the Oz part of it. [The criticism] is also particularly unfair here because we have a really large eyes-on pro scouting department with a voice. Matt Daly, who’s our head of pro scouting, and Tim Naehring (VP of Baseball Operations), they combine predictive analytics with eyes-on [scouting)]. In any decision, they’re consulted.

“Analytics is information and information is currency. And information is always important. … The other problem is very few people are good at math. I don’t like math. I’m not good at math. I refuse to learn my times tables. I didn’t think it was necessary. I was a visionary. We’ve got calculators now. But I don’t have any problem with people who are good at it. But I think people just fear math.

“You know when “Moneyball” came out, it was revolutionary and fans loved it. Everybody loved it. And the criticism back then was, ‘How come you can’t be more like Billy Beane? How come you can’t be more like the Oakland A’s?’ And now it is, ‘They are not using humans and they are using simulations and it is all about numbers now.’ P.S., it’s always been about numbers.”

JS: At this moment, part of the issue is what came first is what people are comfortable with. If RC+ was devised in the 1870s and I came along with batting average today, I would be told to stop trying to re-invent the game.

Numbers and evaluative processes aside, Afterman emphasizes that it is Cashman, himself, that so many do not appreciate in full..

JA: “Brian takes the slings and arrows. He takes the criticism. He takes the negativity. And he just does his job. That’s what I think is the most important thing. You mentioned people who have run from organizations when it starts to go bad. He just does his job. He’s at his desk whether it’s 30,000 feet in the air flying between New York and Tampa, whether it’s at Yankee Stadium, whether it’s on the road. … I wouldn’t work for somebody who’s lazy. I wouldn’t work for somebody who shirks their responsibility. I wouldn’t work for somebody who doesn’t understand that part of baseball.

“It is not all glamorous. Seventy percent of it is the mundane business of baseball; the stuff that fans wouldn’t even want to know about (Afterman snores to emphasize the tedium of it). Everybody has the right to an opinion, but I just think that, like so many things in the United States, we express our opinions all the time, we’re used to expressing our opinions and we are used to, thank God, having the freedom to express our opinions. In some states, you do not have the right to express your opinion. In some you do. Baseball lives in one of those states in which you can express your opinion.”

JS: Do you think if Cashman wins another championship (which would be his sixth while working with the Yankees and his fifth as GM), he would retire?

JA: “I don’t think he, quote, unquote, wants to win another championship and walk away. He was a child and grew up in this organization. He went from the mailroom to the boardroom. And it’s the only thing he has known. It’s something he enjoys doing. I think he will walk away when it’s no longer enjoyable.”