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MLB Winter Meetings Will Be Scott Boras's Show Once Again

Representing the top three free agents, Scott Boras holds all the cards as the baseball world convenes in San Diego for the Winter Meetings.

Rarely have the annual baseball Winter Meetings belonged to one agent the way the ones next week belong to Scott Boras. He represents the three free agents this winter who are expected to sign contracts of at least $150 million: pitchers Gerrit Cole and Stephen Strasburg and third baseman Anthony Rendon.

No agent ever has negotiated three free agent deals that big in the same off-season, and when Boras is done he will have negotiated 13 of the 37 biggest contracts in history.

Oh, and by the way, he also represents free-agent pitchers Hyun-Jin Ryu and Dallas Keuchel, outfielder Nicholas Castellanos and third baseman Mike Moustakas, who already signed with Cincinnati for $64 million over four years.

By the time Boras is done he will have negotiated free agent deals worth close to what the entire free agent class of 10 years ago secured: $847 million.

The key phrase here is “by the time ….” because baseball will operate next week not on its time but on Boras Standard Time, which usually means the agent is in no hurry to get his biggest deals done in San Diego.

Over the previous 12 winters, Boras has negotiated 14 free agent contracts worth at least $75 million. Only one of them wrapped at the winter meetings, and that deal, between Jayson Werth and the Nationals in 2010, technically happened on the eve of the meetings. Most haven’t come close to happening at the meetings.

Circle Jan. 17 on your calendar. Since 2008 that is the average date for Boras clients to sign free agent contracts worth $75 million or more. Only two of the past 14 Boras clients to sign a mega-deal returned to his ballclub, Chris Davis and Matt Holliday. 

Boras Free Agent Contracts Worth At Least $75 Million, 2008-18







Bryce Harper



Feb. 28


Eric Hosmer



Feb. 19


J.D. Martinez



Feb. 19


Jake Arrieta



March 11


Chris Davis



Jan. 16


Wei-Yin Chen



Jan. 12


Max Scherzer



Jan. 21


Jacoby Ellsbury



Dec. 3


Shin-Soo Choo



Dec. 21


Prince Fielder



Jan. 26


Jayson Werth



Dec. 5


Adrian Beltre



Jan. 5


Matt Holliday



Jan. 5


Mark Teixeira



Dec. 23

While baseball would love to promote the Winter Meetings as a fast-paced frenzy of trades and signings, Boras doesn’t operate that way–not under artificial deadlines. It’s not that he believes time is on his side. He believes it is irrelevant, at least when it comes to elite talent. As you can see from those past 12 mega-deals, nothing gets discounted when you shop at Boras Corp. after the holidays.

Indeed, one of Boras’s proudest moments was securing $330 million for Bryce Harper after a tepid season in which he hit .249 and because of a drop in slugging and poor defense tied for 183rd in WAR, right there with the likes of Kevin Plawecki, J.T. Riddle and Nick Martini. Rarely has a player commanded such premium money off such a down “platform” season.

That we have arrived at this Boras triple-witching hour at the meetings is due to serendipity and his own industry. Cole, for instance, while attending Orange Lutheran High School in Orange, Calif., played in the same league as Boras’s son, Shane. With his analytical mind, Cole was impressed by how Boras saw the game in great depth. He hired Boras as his advisor as a high school senior.

Cole and his father, with help from Boras, did their research and drew up spreadsheets to figure out the earning potential of a pitcher who signed out of high school vs. a pitcher signed out of college. That’s how in 2008 he said “no” to the New York Yankees when they drafted him in the first round, 28th overall, and attended UCLA. Three years later, he signed an $8 million bonus with the Pittsburgh Pirates as the first overall pick in the draft.

Now Cole is the Yankees’ most prized free agent target since they went after CC Sabathia and won over his West Coast preference. Boras can work the Angels and Yankees against one another (with interest from the Dodgers). Both need him badly.

Don’t undersell the Yankees’ hiring of pitching coach Matt Blake in their pursuit of Cole. GM Brian Cashman has pushed back-room analytics for years, but he understood now was the time to own it in the storefront window, too. Four years ago, Blake was coaching high school ball. Now he’s a tech-savvy, cutting edge thinker who understands the kinetic chain of pitching and easily communicates such knowledge. That he never before worked with major leaguers is not especially relevant. The guy is a teacher, and Cole is a pitching wonk who soaks up as much knowledge as any pitcher out there. Cashman made sure to bring Blake with him when he visited Cole this week.

Blake, now 33, is just four years older than Cole. Blake was just out of Holy Cross and working for a lithograph company when Cole and Boras were turning down the Yankees.

Good luck to the field trying to keep Cole away from the Yankees this time. You’re going to have to out-bid New York at a time when it is in its longest title drought in the wild-card era and when it just sold streaming rights to its games to Amazon.

The year after Pittsburgh drafted Cole, Boras represented another No. 1 overall pick, Strasburg, who had gone undrafted out of high school. In May of 2016, Strasburg went outside the usual Boras playbook and signed a seven-year, $175 million extension with Washington six months before he was about to hit free agency at age 28. But in the deal Boras also secured an opt-out clause after three years. Now Strasburg can turn the four years and $100 million that had been left on the deal into upwards of $175 million. The Nationals still look like the favorites to keep him.

In the 2011 draft Boras represented Rendon, a third baseman at Rice drafted sixth overall. Rendon is 29 and coming off his best season, with an OPS of 1.010. It’s unlikely the Nationals can afford both Strasburg and Rendon. The Dodgers can make a run at Rendon with a contract similar to what they considered for Harper: a short-term deal with a huge average annual value. Texas also is in on Rendon.

In the past month Boras has met with the Rangers in Houston regarding Rendon and with the Yankees, Angels and Dodgers in California regarding Cole and/or Strasburg. That’s just the start.


The baseball winter runs through Boras. He holds the cards to the Nationals’ chances of repeating their World Series win, to the balance of power in the American League, to the Yankees’ hunger to end their drought, to the chances that Mike Trout wins a postseason game in the near term, to whether teams such as the Rangers, White Sox, Angels and Padres become the next team to jump from a losing record one year to the playoffs the next, and what the next pay ceiling for pitchers will be.

Eleven months ago, the free-agent landscape looked so bleak for players that agent Jeff Berry put out a memo to players that sounded like a call to arms. It read in part that “in this new world order of analytics, aging curves, tanking, shifting, openers, bullpenning, declining attendance and declining salaries, players should and do feel vulnerable and unsure.”

This market is off to a much better start for two reasons: 1) a better free-agent class and 2) when it comes to where teams sit on the winning curve (the biggest factor in spending), more teams are on the incline.

After signing one-year deals for $6.5 million and $10 million, Moustakas broke the bank with a four-year deal. Drew Pomeranz signed a four-year deal, the first pitcher who doesn’t start or close games with that kind of deal since Brett Cecil. Zack Wheeler, with stuff and a career that resembles those of Darren Dreifort and Mike Foltynewicz, pulled down $118 million. Will Smith got Zack Britton money with less of a body of work. The White Sox, a team that hasn’t had a winning season for seven years, hurried to enrich Yasmani Grandal with $73 million.

Boras said the pace of negotiations this winter is far greater than what happened last year.

"It's been very different," he said Friday. "I've had meetings with ownership groups for 14 consecutive days. I'm not even sure last year with Bryce that I had one meeting like these until around the holidays. The landscape is completely different."

Maybe this market is so heated that next week Boras actually has a deal to announce at the Winter Meetings. Cole? Strasburg? Rendon? Ryu? It would be just like old times, like 2000, when he pulled off the $252 million stunner for Alex Rodriguez with the Rangers. That was back when Boras would spend $35,000 on satin-covered binders with glowing statistical projections for his client. Now every team has roomfuls of servers with proprietary data. The books were vanity projects then and worth even less now.

Cole and Strasburg are true aces at a time when such a supply is dwindling. Rendon is one of the 10 best hitters in the game, maybe even better than that if you like your hitters to hit for power and put the ball in play.

No satin-covered books required. The balance of information may have flipped, but Boras understands the real currency is talent, and at the Winter Meetings it will be obvious that he has the best available.