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Behind the scenes with player agent Scott Boras at baseball’s Winter Meetings

Scott Boras in his suite at the Winter Meetings with a presentation on Anthony Rendon, one of his clients. On the TV behind Boras, Mike Lowell discussed the Stephen Strasburg extension, another deal brokered by Boras.Michael Silverman

SAN DIEGO — Scott Boras sits on the white leather couch in his fifth-floor hotel “war room” at the Winter Meetings, scrolling through the photo album on his phone.

It’s a couple hours past midnight, and Boras is red-eyed from another day in a three-week span in which he’s averaging about 3-4 hours of sleep a night. He is determined to find the video of his and daughter Natalie’s dance at her wedding two months ago.

Twelve hours earlier, Boras had wrapped up Stephen Strasburg’s record-setting seven-year, $245 million contract with the Nationals.

Later that night, he would finish off Gerrit Cole’s record-smashing nine-year, $324 million deal with the Yankees.


One evening later, he bookended the meetings with Anthony Rendon’s seven-year, $245 million deal with the Angels.

A three-client, $814 million trifecta. The most high-profile agent in baseball is at the top of his game.

.   .   .

With a large-screen TV on mute tuned to the MLB Network showing talking heads breaking down the Strasburg deal and nearby dishes of the chocolate- and powdered-sugar-dusted almonds and peanuts that Boras says team owners and general managers can’t resist, Boras is laser-focused on finding the video.

A question about the last time he had put away his phone over the last couple of months had served as the primary trigger for wanting to find the dance video.

Answer: He had handed the phone to a colleague before the wedding with instructions to keep it away from him — unless he got a message that sounded urgent.

Just a few weeks before the wedding, while Boras was jetting around the country conducting business, Natalie had asked her dad to learn a Luis Miguel song for their dance, a 3½-minute number with a daunting number of steps, dips, and twirls.

Boras could not say no. In his hotel rooms and at home, Boras practiced, breaking the dance down to 47 steps, which he broke down into small segments, committing the steps to muscle memory, one by one.


The bandwidth required to learn, never mind perform, the dance — on top of the mounting pressure of laying the groundwork for the deals he would consummate in San Diego — sent Boras into a pitch of high anxiety.

When he finds the video, Boras presses play and holds out the screen, a beaming smile on his face. He is a perfectly competent dad dancer. He is not without rhythm. He doesn’t trip, he doesn’t step on or drop Natalie. Afterward, he reports, his daughter told him, “That was perfect, Dad.”

Boras lingers on the topic of the dance and the wedding. Besides being a source of such happiness, it also serves as a gateway to a greater point he wants to make about his work uniting players with owners. But before he can quite get there, Boras, in his patented deliberate and patient negotiating style, circles around this moment, this war room, these meetings, and the industry-shaking deals he is orchestrating.

He is eager to describe what’s in and what goes on in the war room — this war room, that is. He has another room set up in a different San Diego hotel for clients and teams to meet without setting off alarm bells among the media, teams, and agents swarming the lobby and hallways here at the Manchester Grand Hyatt, headquarters for the meetings.


The room had been filled with a dozen Boras Corp. members when a visitor entered, but they quickly dispersed. Unsurprisingly, they left behind no traces of their work. No names of teams, no lists of offers — the room’s been scrubbed and all but wiped down for fingerprints. Only a bottle of Advil sitting by a closed laptop hints at the groundwork and preparation that goes into the complex courtship ritual of a free agent signing.

Complete team

Scott Boras greeted Peter Gammons in the halls of the Winter Meetings.Gregory Bull/AP/Associated Press

The Boras Corporation has 137 employees, 70 based in Newport Beach, the rest in scouting and development spread out across the country, plus Japan, Korea, Taiwan, Venezuela, Puerto Rico, and the Dominican Republic. A 35-member research staff has been crunching statistics and financial data to prepare Boras and the crew who made the trip to San Diego.

“We have different responsibilities for everyone for what they do here” at the meetings, said Boras. “Tracking existing signings, interest levels, fielding the phone calls from the teams and essentially be able to be in contact with all major league teams at all times through this process. You have to have a large staff to do that, you have to be very comprehensive and prepared, and their job is to prepare me as I shift through the meetings.”

The room is well stocked, and alcohol-free. Bowls of apples, oranges, bananas, goldfish crackers, bags of Clean Snax, with Melissa’s brand red grapes kept in the fridge.

Never far from Boras’s reach is his go-to snack, a bag of dried prunes.


Boras points to a table, with disconnected wires and cables underneath it, remnants of a high-speed link to the stored data banks in his Newport Beach office 85 miles to the north.

A couple of “Anthony Rendon” aluminum-covered three-ring binders are lying around, each overflowing with compelling data and statistical information pitched for a team to sign Rendon at the valuation Boras wants.

Two black-covered binders contain 15 tabs and sections each, one for the National League, one for the American League.

Boras opens one to the Red Sox section and starts flipping through, more quickly on the pages that contain proprietary information.

Related: Final thoughts from baseball’s Winter Meetings

“I’ve got their entire budget for the next three years, I’ve got their roster, so I can tell you what their amount of guarantee is, I have their ranks — offense, defense, pitching — in the MLB, what their strengths and weaknesses are at each level of the minor leagues, the luxury-tax dynamics of what they do, the overage penalties, I have minor league players, who’s coming, going forward, then I have their franchise values, I have their revenues, gate receipts, attendance, local rights and TV value — all those kind of things that give a general summary, and I have that for each team in baseball,” said Boras. “I really know everything about every club as far as basic data.”

Scott Boras with a binder of data on the Red Sox.Michael Silverman

The meetings with owners and top executives on Strasburg, Cole, and Rendon took place in the weeks leading up to the Winter Meetings. Those in on Rendon flew to Texas (Rendon’s wife is pregnant), while the others flew to southern California for Cole, Strasburg, and/or another top pitching free agent client, Hyun-Jin Ryu, based in Korea.


As Boras is talking, the chyron under the TV talking heads speaking in the lobby below asked, “Why has there been so much early action in this market?”

“Why? Because Toronto, Cincinnati, the White Sox, the Marlins, the Yankees, the Dodgers, they’re all in the market — and, there are elite starting pitchers in the market that will not be available next year,” said Boras. “That’s why.”

Boras described the high-level meetings among clients, their wives, and teams as imperative to discovering a mutual comfort level before the economic discussion can begin.

“Teams would come in and we’d have literally 6-7 meetings,” said Boras. “They’d make presentations. I take notes, 30, 40 pages of notes. I listen to conversations. I make sure I have the player and his wife talk and ask questions. I have a list of things they want to ask. We prepare the list for them, but often it’s a dialogue, a good conversation. The team comes in and talks about their franchise for two or three hours. Owner, GM, assistant GM, the manager often comes, they usually bring some of their veteran players who are historical to the franchise and then they talk about what it means to be a member of that franchise.

“We talk clubhouse rules, travel, trainers, medical, you name it. Then I have a list of questions that I direct to the team after I listen to everything, to ask them questions to make sure that we’ve given them an appropriate view of the club.”

Boras probes owners about what kind of players they want, whether they’re willing to add players mid-season, and asks managers about how they motivate and how they coach.

When the meeting ends, Boras listens for his client’s impressions — good or bad.

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“A player comes out of the meeting and he’s like, ‘Not for me,’ ” said Boras. “And the owners think the meeting went great. The player goes, ‘I didn’t like this, I didn’t like that, I didn’t like what he said, I can’t trust him.’ ”

When the sides click but the team on the player’s wish list does not make a good enough offer, that’s when the player tells Boras to do his job, telling him, “Make sure one of those teams does do that.’’ Which they often say. And the answer is, you have a job of advocacy.

“Like with J.D. Martinez, I met with [Red Sox chairman] Tom Werner a couple times, got [principal owner] John [Henry] on the phone,” said Boras. “I really just said, ‘This guy can make a monstrous difference to your team, and our algorithm metrics indicate your probability to win a World Series is much higher with this player.’ And it took time. Then Dave [Dombrowski] and them, they finally agreed. And at Dodger Stadium, at the end of the [2018] World Series, they were very kind and we enjoyed a glass of champagne together to talk about that. That helps your credibility going forward when you’re dealing with owners and people.”

Big moments

Anthony Rendon, one of Boras’s clients, signed a seven-year, $245 million deal with the Angels on Wednesday.David J. Phillip/AP/Associated Press

It’s the success stories, the pre-meetings deal he had struck with longtime client Mike Moustakas and the Reds (four years, $64 million), the Strasburg deal, and the Cole and Rendon deals that are on the verge of being finalized, that bring Boras back to his daughter’s wedding.

After trying to convey the magnitude of the deals he works on, the pressure he feels to make his clients happy, and the thrill and contentment he gets when a deal gets made, his eyes glisten. He is reminded of how he broke down when he made a toast to Natalie and her husband, Luke.

“I had to stop and collect myself to go through it,” said Boras, unabashedly. “Of course I find out later, this is what women love. They love to see fathers cry at a wedding — it’s such a permissive event. But it was really something for me. I don’t think I’ve experienced something where you look at your life and you can say, ‘You know, the job I do is so personal to the people I represent because it’s their lives.’ And you do something in your family with your daughter, it’s a one-time event that wedding is, a special one-time event in their lives.

“And this process,” said Boras, meaning the war room and its surroundings, “is normally a one-time event.

“It is a big, big moment.”

Three big, big deals added up to three big, big moments for Boras’s clients, in what was hardly a war room.

Peace and prosperity reigned here.

So did Boras, who left town after dancing circles around everyone.

Michael Silverman can be reached at michael.silverman@globe.com. Follow him on Twitter @MikeSilvermanBB