When Juan Soto turned down a $440 million contract from the Washington Nationals in 2022, everyone thought he was crazy. Soto was only 24 years old at the time. He had just won a World Series with the team a few years prior, and now he was turning down the richest contract in Major League Baseball history — by more than $100 million.

However, while rumors started to leak that Soto was young and greedy, the truth is that it wasn’t entirely his decision. Soto’s agent, Scott Boras, had quietly convinced him that the Nationals weren’t committed to winning, and if he continued to play well over the next few years, an even bigger contract by a better team would be waiting.

The craziest part is that Boras was right. The Nationals haven’t finished above .500 since the team’s World Series win in 2019, and Soto is now projected to sign a deal worth between $500 million to $600 million this offseason. But this thought process is also why the New York Times has labeled Boras “the most hated man in baseball.”

A former baseball player who topped out in Double-A in 1977, Boras went to law school before stumbling into baseball representation. Boras was working as a pharmaceutical defense litigator when a former teammate asked him for help on his contract. Boras got permission to do the deal from his law firm, pitching it as pro bono work on behalf of young baseball players entering the MLB draft, with the firm unaware they would end up kicking off one of the greatest careers in sports history.

Scott Boras then founded the Boras Corporation in 1980 and is easily the top dog in baseball today. Boras is the man behind some of the sport’s biggest deals, negotiating the first-ever $50 million, $100 million, $200 million, $250 million, and $300 million contracts in MLB history. And Boras’ client roster includes enough hardware to fill a gymnasium with the long-time MLB agent, or as he likes to call himself, “baseball attorney,” representing 13 MVP winners, 11 Cy Young winners, and 4 Hall-of-Famers.

Scott Boras’ Record-Breaking MLB Contracts

• Bryce Harper: 13 years, $330 million

• Corey Seager: 10 years, $325 million

• Gerrit Cole: 9 years, $324 million

• Xander Bogaerts: 11 years, $280 million

• Alex Rodriguez: 10 years, $275 million

• Max Scherzer: 7 years, $210 million

• Barry Zito: 7 years, $126 million

Scott Boras’ record speaks for itself. It’s estimated that he has negotiated nearly $10 billion in contracts for his clients — all guaranteed — and Boras is so good that some believe he will eventually be the first agent inducted into the Baseball Hall of Fame.

But what makes Scott Boras such a good agent? Why do many of the world’s best players run to him when it’s time to get paid? And what does Boras do to make MLB teams lose sleep at night when he shows up on the other side of the negotiating table?

We could spend hours talking about his insane work ethic, attention to detail, and ability to see what others don’t in the business of baseball. But that’s sort of table stakes; you don’t get to where Scott Boras has gotten without hard work and intellect.

Instead, Boras is known as a tough negotiator with an uncanny knack for finding any possible leverage or loophole, and then using it to his and his client’s advantage.

Scott Boras was one of the first MLB agents to start aggressively promoting analytics throughout the 2000s, and his free agency binders have become the stuff of legend.

The best example of this is Prince Fielder’s free-agent debut in 2011. The Milwaukee Brewers first baseman had just completed another All-Star season, finishing third in NL MVP voting, and he wanted to secure a big deal before hitting 30 years old.

So, Scott Boras went to work. Boras put together a 73-page binder now known as “The Book.” Inside, MLB executives found nine different sections where Boras used statistics to showcase everything from Fielder’s home run power to his durability.

For example, the binder included quotes from Fielder’s manager and teammates, like when Ryan Braun called Fielder the “strongest man in baseball.” The binder also had a section titled “Built Fielder Tough,” where Boras noted that Fielder was one of only ten players in MLB history to appear in at least 959 games over any six-year span. And the projections section was even more optimistic, with Boras using statistical analysis to point out that Fielder was on pace at the time to join Jimmie Foxx, Mickey Mantle, Eddie Matthews, Mel Ott, and Babe Ruth as one of just six players in MLB history with 400 home runs, 1,000 RBIs, and 1,000 walks at or before the age of 32 years old.

These binders have become less impactful as many MLB teams now have fully staffed, disciplined analytics departments. But every once in a while, one of Boras’ binders will find its way to a team’s owner, and they’ll override everyone to close the deal.

“There was one instance where it proved to be a very, very important part of the team’s consideration,” Boras told ESPN in 2011. “The general manager gave it to the owner, and he looked at it and said, ‘Wow, I didn’t know this guy was that good.'”

But these overly optimistic projections work both ways. One of Scott Boras’ most notable deals was when he landed Barry Zito a 7-year, $126 million contract with the San Francisco Giants in 2006. That’s because while Boras’ book showed statistics that Zito was on his way to becoming an all-time great, Zito’s time with the Giants was a disaster, and it’s now considered one of the worst deals in the history of free agency.

Then again, Boras isn’t necessarily concerned with how his client performs after signing a contract. His job is to get his clients the most money, which he did for Zito.

Boras doesn’t just put together binders, though. He often hypes up his clients as “generational prospects,” routinely advising them not to waste time negotiating with their current team so they can increase overall demand by hitting the open market.

Some MLB teams have actually refused to draft prospects represented by Scott Boras because he is known to game the draft slotting system. J.D. Drew, for instance, was drafted second overall by the Phillies in 1997. But the Phillies only offered him $3 million, so Boras advised him to spend a year in independent ball, securing Drew a $7 million contract with the Cardinals just 12 months later as the fifth overall draft pick.

Boras isn’t just an agent, either. He has invested a ton of money in his clients, like opening a marketing division for endorsement deals, and he even owns a few training facilities in California, Florida, and Arizona. These training facilities aren’t a super profitable business compared to the hundreds of millions of dollars Boras has made in agent fees, but they provide his clients with a place to train during the offseason and have also served as a resource of integrity for Latin American players hoping to enter the big leagues, especially when it comes to the wrongful (and rampant) use of PEDs.

That’s not to say Scott Boras always wins. His 2023 MLB offseason was particularly tough, as clients like Cody Bellinger, Jordan Montgomery, Blake Snell, and Matt Chapman signed shorter deals than the long-term contracts they all held out for.

But if history tells us anything, don’t underestimate Scott Boras. The world’s most powerful agent has negotiated more money in player contracts than anyone else in history, and Soto’s $600 million potential payday will be just another feather in his cap.

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