The art of a deal at the Winter Meetings

LAKE BUENA VISTA, Fla. – The first time Alex Anthopoulos attended the MLB Winter Meetings, someone had to stay in the team hotel suite at all times to monitor the room phone. The Toronto Blue Jays general manager remembers waiting anxiously to hear from other clubs.

“If someone called, you’d better not miss that call,” Anthopoulos says. “This is before cell phones, or no one had them, so you had to sit there by the phone and people would call the room.”

When the phone rang, everyone would get quiet with anticipation.

“You take the phone and everyone’s listening to what they say until they hang up and then you announce it to the room and you start talking,” Anthopoulos says.

Back then, teams would send scouts and executives to the hotel lobby to gather any information. Now they send text messages and emails from the comfort of their hotel suites.

It’s just one example of how the Winter Meetings have evolved from a mid-winter get together to a four-day frenzy of non-stop rumours, speculation and activity.


The days of calling the hotel room phone ended once every agent and team official starting arriving at the meetings armed with an iPhone or Blackberry. Anthopoulos now prefers to set up meetings by texting, calling and emailing his counterparts.

“A meeting I had today was off a text at three in the morning last night,” he says. “I heard back at four and it’s like ‘let’s meet today.’”

In other words, there’s virtually no break in the action for days on end. Sleepless nights and bleary-eyed mornings are commonplace. Once the meetings get going, some teams prefer large gatherings where each side has key officials available to provide insight if called upon.

“When you have these meetings and you get ten on ten it’s like having an audience,” Anthopoulos says. “GM and GM are talking and you’ve got nine people around you and nine people on the other side and no one says a word, it’s just like a stare-down. It doesn’t make any sense.”

Instead of getting bogged down with large meetings or extensive hypotheticals, Anthopoulos favours direct one-on-one contact with high-ranking officials from rival clubs.

“Now it’ll just be ‘let’s just send a text,’” he says. “Let’s just text the GM real quick. We don’t have to spend five hours by this.”

So far it hasn’t led to any moves for the Blue Jays, but that could change. Viewed by team executives and agents as an extremely thorough operator with an incredible capacity for work, Anthopoulos makes sure to weigh as many options as possible.

“When you’re down here it’s all you’re doing. This is what we’re here for,” Anthopoulos says.


It’s easy to get distracted on the site of the 2013 Winter Meetings, the Swan and Dolphin Hotel. Hundreds of team executives attend, from interns fresh out of college to veteran general managers Billy Beane and Sandy Alderson to living legends such as Tommy Lasorda and Jim Leyland. The Blue Jays alone brought a full roster’s worth of employees to Orlando this year.

“We have probably 30 people that come to the meetings, but they’re not in the suite all of the time; they come in and out,” Anthopoulos says.

While texting and emailing accounts for a massive percentage of communication between teams and players, deals do get consummated the old-fashioned way. As I was speaking to a club executive Wednesday, two agents approached and started selling the official on a free agent client they represent. The executive expressed interest and encouraged the agents to keep lines of communication in a brief conversation that would not have been possible any other week of the year. Only at the Winter Meetings could such a chance encounter occur.

For Anthopoulos conversations with agents are not the top priority.

“You have a lot of agents that want to meet and I try to be respectful,” he says. “I’d rather try to take this time to work with teams if we can since it’s a lot harder to do that. We talk to agents at all times.”

Hundreds of agents gather in the hotel lobby, talking shop with one another and pumping up their clients to reporters and team executives for hours on end. Part of the crowd is there for the first time, looking to make connections. Others — such as former Blue Jays GM J.P. Ricciardi — are so well-connected that they can’t stand in the lobby for more than 30 seconds without greeting another familiar face. It’s not uncommon for those in the industry to stay out late, comparing notes on the market or catching up with old friends.

“I stay as long as I’m being productive, whether that’s 10 p.m. or 1 a.m.,” one veteran agent said. “As soon as I’m no longer being productive, I’m gone.”

Outside of the expansive media workroom there are numerous live radio stations and approximately ten TV sets broadcasting the latest news and rumours from coast to coast. The spectacle puts baseball in the national spotlight for four days, but it’s not necessarily conducive to deal-making.

“It’s actually not as productive as you would think just because everyone’s just together all day in a suite and this is all you’re doing,” Anthopoulos said. “Some people have 60 bodies in their suites and you’re trying to get things done and trade proposals and there’s just no room in these suites.”

Many team executives still say they feel pressure to complete a deal at the Winter Meetings. They have to remind themselves that there’s no real deadline in play. As a second veteran agent remarked Wednesday, plenty of time remains after the meetings end Thursday.

“There’s no prize for having the best team in baseball on December 11,” the agent said.

That message might be heartening for Anthopoulos, who faces pressure to add starting pitching and address needs at second base and on the bench. He’ll continue working his cell phone through Thursday in the hopes of making a deal. Yet in the end it may be simplest to complete a deal after getting a little rest and returning to the comfort of the team’s Rogers Centre offices.

“People are throwing out all sorts of ideas and some people get a little paralyzed with some of this stuff too,” he says. “It’s almost like the smoke clears a little bit when you leave and you can get back to work.”

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