This is the 24/7 life of a modern baseball executive, who operates in a world where analytics have already altered the way rosters are constructed and in-game strategies are carried out. Technology has also altered how the sport’s decision-makers communicate with one another — in humorous, contemporary ways.
The haggling over the phone, or even in person, still goes on, of course, but is now being supplanted in part by more and more text messages, emojis and GIFs. Yes, even GIFs.
“My wife, in particular, loves that we’re texting and calling people all the time,” Mike Chernoff, the general manager of the Cleveland Indians, said with more than a little sarcasm in his voice. “It’s really helped our relationship.”
In the life cycle of baseball, the two periods of intense front-office activity are the days leading up to the July 31 trade deadline and the off-season, when rosters are revamped, more trades are arranged and free agents are signed.
During his 15 years as the G.M. of the Colorado Rockies, from 1999 to 2014, Dan O’Dowd said, most of the trades and negotiations with agents were done over the phone, either landline or mobile.
But near the end of his tenure with the Rockies, communication began to change dramatically.
O’Dowd said at the last of his winter meetings, which are essentially baseball’s December convention, “I spoke almost exclusively via text to G.M.s despite being in the same exact building.”
He added: “I’m not saying that’s a good thing, but that’s what it’s evolved to.”
All this is a far cry from the scene in 1975, when Bill Veeck, the irreverent owner of the Chicago White Sox, and Roland Hemond, his general manager, set up shop in the hotel lobby during the winter meetings with a landline phone and an “Open for Business” sign.
And while it was a stunt right out of the Veeck playbook, the two men quickly pulled off several trades.
When Thad Levine, the general manager of the Minnesota Twins, started working in baseball in the late 1990s, most general managers traveled frequently with their team — as well as to the All-Star Game or World Series, and of course to the general managers’ and winter meetings — with the express purpose of meeting face to face with their counterparts to initiate trades.
“But today, we negotiate hundreds of millions of dollars of contracts and make massive trades without ever picking up the phone and speaking directly with one another, let alone meeting face to face,” Levine said. “You kind of learn the personalities of guys — who needs a phone call, who can do it on text, who prefers emails, who likes to be lighthearted. The art of the negotiation has almost been trumped by the art of communication.”
Over the years, general managers have trended younger — most now are in their 30s and 40s — which means they stay on their mobile phones constantly. The younger ones, after all, came of age in an era when texting was used for everything from updating your mother on your whereabouts to breaking up with a not-so-true love.
“The day that I feel like I leave my cellphone somewhere, that’s when panic will set in,” said Dipoto, 49, who has sent countless text messages to put together more than 60 deals to overhaul the Mariners’ roster since he took over in the fall of 2015. “I’ve been known to respond with some GIFs and occasional emojis.”
Even Sandy Alderson, the Mets’ general manager, who, at 70, is the oldest person doing that job in baseball, is getting in on the action.
“I did send a smiley-face emoji to Brian Cashman the other day,” he said recently in reference to the Yankees’ general manager. He declined to say why.
Not everyone has gone nonverbal. Alex Anthopoulos, 40, the new general manager of the Atlanta Braves who previously ran the Toronto Blue Jays, mostly uses text messages to set up phone calls. The back and forth via text takes too long, he said.
“My preference is more on the phone,” he said. “You don’t know how something is going to get delivered in tone.”
Dipoto said Levine, 46, is the wittiest of all his peers when it comes to text messaging. “Whatever wittiness I have was genetically passed down to me by my father,” Levine said. Erik Neander, 34, of the Tampa Bay Rays, and Cashman, 50, are also personal favorites of Dipoto.
“Cash gets his point across,” Dipoto said.
Added Levine: “The person who has the most expansive library of GIFs that he employs for negotiations is none other than Brian Cashman. He is exceptional. They’re extremely funny.”
Still, messages can be lost in translation.
Chernoff, 36, said emojis may cause confusion. His favorite interaction was when he was negotiating with an agent and made a formal offer. “And I got back just this,” Chernoff said, imitating a thumbs up emoji. “Not to accept it but to say that he got it.”
As a result, Chernoff said, baseball executives still have to step back sometimes and place a phone call — “just to make sure the context is there” — because things can get misinterpreted in text or email.
And some executives are mindful that when they negotiate by text, they create a digital paper trail, which can be good — or a headache. And texting does not have the organic back and forth of a call.
“It’s all about the timing and the flow of the negotiation,” Levine said. “At the outset, you may feel each other out by text. In the middle, you tend to get on the phone to make sure you’re not giving too much before they give something. And then at the end, you may go back to text or email to make sure you’ve got all the points on one piece of paper.”
The change in the way general managers communicate has also had an effect on agents. Scott Boras, baseball’s best-known agent, said he built a 1,500 square-foot “negotiating compound” in his Southern California home where he spends much of his days in the off-season. He has workout equipment, a bathroom, a refrigerator, numerous televisions and computers, and a view of the ocean.
Boras still meets in person with team owners and general managers, but he also has a phone number solely for their text messages. He tells them to text him with a window when they can speak. He also maintains a list of which general managers prefer to text and which prefer phone calls. “It used to be widely in favor of talking,” he said.
The modern way of negotiating is “grossly more efficient,” Boras said. But the bulk of negotiation is still done by talking, and text messaging is only for nailing down the details, he said.
“I end up talking a lot because I have a lot of information to exchange and it would take me hours to text it,” he said.
But texting can also be quick, and quite to the point.
During the recent winter meetings, Chris Antonetti, the president of the Indians, thought he was making progress with another general manager on a potential trade. “I guess I gave him an answer he didn’t like,” he said,” and he sent back a GIF that was quite colorful.”