Ask Yankees Senior Vice President and General Manager Brian Cashman to break his job down into the simplest terms. What follows could pass for a movie's blooper reel.
"Essentially, I'm the director of baseball operations, in charge of creating a culture, the hiring process … no wait."
"Let's see, how best to put it … I'm the director of baseball operations and my job is to create a culture and philosophy and hire personnel that best allow us to execute those efforts in terms of developing players. I'm bouncing all over the place, sorry."
"I should be able to do this better. So as director of baseball operations, you know, we have nine Minor League affiliates, now. So I'm the head of baseball operations, hmm -- I'm trying to think of something that's condensed enough."
"Basically, I guess I'm at the top of a pyramid of people that I hire to help execute a philosophy that was taught to me in years gone by about trying to run a full-service baseball operation, which entails acquiring amateur talent, then developing pro talent, which culminates into wins at the Major League level for ownership and the fanbase to enjoy."
For as much as he struggles to describe his job, Cashman is one of the best in the business at it.
In the movie version of the Yankees' 2017 season, Cashman is not the director -- that's Manager Joe Girardi. And Cashman is certainly not an actor in this movie -- the guys wearing pinstripes on the field play those roles every day. No, Cashman is the screenwriter, and if World Series rings equate to best screenplay Oscars, he has proven to be one of the most prolific writers in the game.
Two Thumbs Up
Hired by the Yankees as an intern in 1986, Cashman began climbing the front office ladder. By 1996, he was celebrating a World Series victory as the team's assistant general manager. Then on Feb. 3, 1998, he was elevated to the top job; just 30 years old, he was the second-youngest GM ever.
It was a precarious position, one that came with frequent communication with Principal Owner George Steinbrenner, who made the line, "You're fired," famous long before others tried to claim it. Add to that the fact that the young executive was stepping into a role previously held by Bob Watson, and Gene Michael before that -- two men integral in finding the players that would lead to a Yankees dynasty.
Cashman had worked closely with both men, and he learned a lot from them, including the gravity of the role he was about to take on. And his predecessors didn't downplay the job's import.
"The GM is the most important person in the organization," Michael said. "The GM is more important than the coaches, more than the manager, because the players a GM acquires are the most significant thing. Managers can't make bad players play well."
Naturally, there was a level of trepidation. "Unless you've done something, and you've done it over, and over, and over again, I think it's healthy to have caution," Cashman said. "It causes what you can define as butterflies, trepidation, caution, fear -- they're all applicable. I think it's healthy to be concerned about whether you can or can't do this job, and I had those concerns entering the process. Will I be good enough? Can I do this? Will I be able to make ownership proud and, therefore, the fanbase proud?"
But Cashman had the support of his mentors, and a vote of confidence from Michael bought the young executive the opportunity to continue proving his worth.
"I remember George asking [me] what I thought, and I remember saying to him, 'Brian can do this job for you,'" Michael recalls. "Then after about six months, George lost his patience and wanted to make a change. He wanted me to come back, but I said, 'No. Give Brian a chance and you'll see, Brian can do this job.'"
And he has -- exceptionally well. In nearly 20 years with Cashman as general manager, the Yankees have not posted a losing season. The team has made the postseason 15 times, advanced to the World Series six times, and won it all four times -- a two-decade run that any fanbase in baseball would gladly sign up for.
But the incredible successes of the past have been harder and harder to come by recently. The Yankees' last championship was in 2009, and the team has missed the postseason in three of the last four years.
Still, Cashman and the Yankees continue to plow forward. "The one thing you hear is that, in many cases, experience does serve you well, and I'm as experienced as they come," Cashman said. "I've done this job now, in the biggest market in the United States, for longer than anybody. And I think the successes and failures, whether it's in seasons, or trades, or free-agent signings, or hiring practices with personnel, I think all of that is serving me well as we move forward."
But writing that perfect script for the Yankees, one that includes a parade and some jewelry, seems more difficult every year. And more and more frequently, it includes a lot of last-minute rewrites.
Editing the Script
Without question, Cashman has demonstrated a considerable talent at acquiring top free agents -- Hideki Matsui, Carsten Sabathia and, most recently, Albertin Chapman come to mind -- and making significant trades -- Alexander Rodriguez, Didi Gregorius and, yes, there's that Chapman guy again.
There was one role that Cashman never got to play, though: seller of assets in order to rebuild a team. In fact, that was an idea he had expressed interest in more than a decade ago, during an unlikely time. The Yankees were in the midst of a great run of success, and had recently acquired Rodriguez, the reigning American League MVP, seemingly assuring that the club would be a contender for years to come. But Cashman couldn't stop wondering about life on the other end of the spectrum.
From a 2004 New York magazine profile on Cashman:
Cashman sounds wistful when he brings up the Cleveland Indians, who three years ago tore apart a good-but-aging team, sinking to last place in order to rebuild from scratch. "To be the guy who everyone else is calling, trying to trade for your one star, and having a choice of prospects to put a new team together …" Cashman said, stretching his hands out toward the Yankee Stadium infield, as if trying to hug a dream. "Yeah, I'd like to try that. But the pain of losing you'd have to go through to get there -- that would be tough."
It was more a hypothetical exercise than anything real; Cashman wasn't about to sell off a team that would appear in that year's American League Championship Series. But last season, Cashman finally had his chance to do more than look at the puppy in the window. Was playing the part of seller as fulfilling as he had envisioned it 12 years earlier?
The short answer is: No. Winning, it turns out, is too sweet to want to endure a complete rebuild. Plus, Yankees fans and ownership have lofty expectations.
Cashman has no complaints about being the big dog, able to buy high to compete. So rather than look at his position as a seller in 2016 as a Hollywood script come to life, Cashman puts a new spin on it. Now it's just another feather in his GM cap.
"I think we do great with free agency, I think we do great at trades, and I think we just checked another box in that we know we can maximize value at the trade deadline as a seller," he said. "I'd rather not be in that position; I'd rather be in a buyer's position. But when your team declares itself a certain way, you've got to put your finger up in the air, see which way the wind is blowing and assess yourself correctly.
"I think we did that last summer. The team had a good three months to prove what they were, and it turned out we were more pretenders than contenders, so we pivoted and hopefully max-valued out our players and made improvements for the future."
The possibilities of that future are exciting. By adding big-name prospects such as Clint Frazier, Gleyber Torres, Justus Sheffield and others to the farm system, the Yankees appear to be set up well for seasons to come. But Cashman will be the first to note that a prospect is just another blank storyboard -- the possibilities are endless, but there's no way to know whether what gets written will be good or bad.
"The deadline hit, we made those tough decisions and hopefully benefited from them, but we're not benefiting from them yet," he cautions. "So as we sit here in January, we're still trying to strategize on how we can impact the win column.
"Everything is about speeding up the process of getting this team its next championship. Whether that's in 2017, whether it's closing the gap so it gets delivered in '18 or '19, that's to be determined, but the decisions we made in July are the same decisions we're making now, and the same decisions we were making prior to that. Every decision is about what is going to get us closer to being a world championship contender and eventual world champion."
The decision-making process is an emotionless one for Cashman. It has to be. Whether it's a Yankees draft pick coming up big, a free-agent signing producing or a trade piece making an influence -- whatever works best for the team works for him, too, which is another lesson he learned from those who came before.
"In an organization, you need players who are going to come up and be a part of the Major League team," Michael said. "But you also need players who are going to be chips that are usable in getting players that we need along the way to put together the best team possible."
As a tangible example, Cashman cites how his 1998 deal that sent pitcher Eric Milton and three other players to Minnesota in exchange for Chuck Knoblauch opened the door to sign international free-agent pitcher Orlando Hernandez.
Cashman was high on Milton when the Yankees drafted him in the first round in 1996 -- and Milton was far from a bust, producing a modestly successful 11-year career that included an All-Star Game selection in 2001. But he turned out to be far more valuable to the Yankees as a tradable asset than as a pinstriped pitcher.
Knoblauch played in four World Series with New York, and Hernandez stormed into the rotation in '98 and went 12-4 en route to a parade up the Canyon of Heroes.
"The pride comes in good decisions," Cashman said, acknowledging that sometimes the most dramatic, effective action he can take is standing pat. "If we sign the biggest guy on the marketplace with a ton of money and he performs, there's the same amount of pride as when we trade for Didi Gregorius, who came in here and replaced Derek Jeter. It would be the same amount of pride as when we signed Gary Sanchez, stayed patient with him, believed in him and resisted many trade overtures for him. We hold on, and we get rewarded in the end."
It's September 2016. The Yankees surprisingly are still in the thick of the playoff race thanks to some of the organization's youngest members, including right fielder Aaron Judge, first baseman Christopher Austin and the catching phenomenon, Sanchez.
Over the last few weeks, pitchers Chad Green and Luis Cessa have been holding their own moving between the bullpen and the rotation. Starter Masahiro Tanaka is quietly having a year worthy of Cy Young chatter.
Guys that Cashman drafted, traded for and signed to huge deals are fighting together, scratching and clawing their way through the American League East to try and stay in the playoff conversation.
Although they fall a few wins short, they still changed the conversation. In June and July, the Yankees were scripted to go quietly into the offseason. Instead, Cashman did a quick rewrite, moving the pieces of his chessboard just so, letting the league know that he and the Yankees would not be content with indifference.
His moves proved to be just what the doctor ordered, and the new-look Yankees had an energy about them that left fans excited for what comes next.
The story, though, continues to be a work in progress. Cashman doesn't hide from all of the work that still needs to be done, and he's never afraid to act as he sees fit, ruffled feathers be damned.
"I don't cut corners whether I deal with our personnel director or our media," he said. "I'm always very blunt and very direct. There's a saying I use: Land the plane. I don't need to be taxiing on the runway, I don't need to be circling overhead, I don't need to be diverting or trying to buy more landing time, I just want to land the plane and move on, whatever the subject is. And in most cases, that happens through the media. You can't control how it plays out in the headlines or on the back pages. But you do the best you can."
Cashman admits that the current Yankees squad has question marks, specifically in the outfield, at first base and in the rotation. He says trying to predict the future is like looking through a blurred lens -- the picture gets clearer only as time progresses and more moves are made.
He doesn't want to talk about his job anymore; he wants to get back to doing it. In just a few weeks, the team will take the field, and its play will do the talking. When he made those moves to revamp the Yankees' prospect class last season, reporters, players and even other GMs remarked on a job well done. But praise is fleeting. What others say means nothing unless Cashman can guide his team to the ending he longs to write: title No. 28.
"I remember in '09 when we added another ring to our trophy case," Cashman said. "When I hit the field, I remember the first question I got from a reporter was, 'Some people say you bought this championship,' because that previous winter we had signed Sabathia, Mark Teixeira and A.J. Burnett, and we traded for Nick Swisher. We had a lot of money committed. So they said, 'What do you say to those people who say you guys bought this championship?' And my response was, 'You can call us whatever you want, but you're still going to have to call us world champions, and that's all that matters when the dust settles.'
"I look forward to hopefully getting back to a situation where somebody will be calling us world champions again. That's the end all and be all -- that's why we're in this business. That's why we're doing what we're doing and giving it the max effort that we are."
When the story of 2016 was finished, it didn't include the ending Cashman wished for, but the rewrites he threw in set up some pretty exciting sequel opportunities.
Will the young group Cashman assembled come together to start a new dynasty? Who will play the hero this season? What revisions will Cashman have to make?
If nothing else, that's a pretty good cliffhanger.
Hilary Giorgi is the associate editor of Yankees Magazine. This article appears in the Spring 2017 issue of Yankees Magazine. Get more articles like this delivered to your doorstep by purchasing a subscription to Yankees Magazine at yankees.com/publications.