Scott Boras operates his agent empire from a sleek office complex in Newport Beach, California, but his base of operations often shifts during the baseball season. On game days, Boras frequently sets up shop in a suite at Angel Stadium. When the Los Angeles Dodgers are in town, as they were in October, he’s often found behind the backstop, hosting a steady stream of current and potential clients, as well as those interested in signing them.

The question at hand, though, is whether Boras can still dominate the industry after an offseason that was seen as a setback by some of his competitors.

My College Football Playoff model forecasts how the selection committee is likely to rank teams each week. Last week, my projections included 24 of the top 25 teams, missing only Missouri, whom I had ranked 26th. When it came to accuracy, the model placed 17 teams within two spots of their actual rankings, with the first major miss being the placement of Clemson and Army. While the committee had them ranked 23rd and 25th, I had them at 18th and 19th. Overall, 22 of the 25 teams were within two spots, 16 were within one, and 9 were exactly accurate, including 7 of the top 12.

The Major League Baseball rules prevent agents like Boras from stepping onto the field, so players and executives alike make their way to him.

Before Game 1 of the World Series, Juan Soto made his way to the stands to meet with his agent and Boras Corporation team members. About 30 minutes earlier, New York Yankees GM Brian Cashman did the same. And two weeks prior, before Game 1 of the NLCS, New York Mets owner Steve Cohen had also visited Boras for a chat.

This scene symbolized the upcoming winter’s marquee free-agent showdown: the battle between the Mets and Yankees to sign Soto, whom Boras referred to as “the Mona Lisa of the museum.” It also raised the question that could shape baseball’s offseason: after what some considered a disappointing season, can Boras still command the industry’s attention?

For over four decades, no agent has been more successful at extracting money from MLB ownership than Boras, even as more teams adopt a more frugal approach. After the 2019 season, his clients raked in more than $1 billion in free agency. This winter, Boras is poised to eclipse that figure. According to The Athletic, Boras represents eight of the top 16 free agents, including Soto, who is expected to secure the highest-ever price tag in MLB history, possibly surpassing Shohei Ohtani’s deferred $700 million deal. The rest of his roster includes former Cy Young winners like Corbin Burnes and Blake Snell, home run champion Pete Alonso, and key contributor Alex Bregman.

“It’s the talent that drives the game,” Boras remarked at the General Managers meetings in San Antonio.

No agency has a more talented group of free agents than Boras this winter. However, the market poses serious challenges, reminiscent of the difficulties he faced last offseason. MLB executives and rival agents have pointed out concerns about television deal uncertainties, cautious owners wary of spending with the expanded postseason in play, and a growing reluctance to commit to long-term contracts for pitchers.

This offseason will be a test of Boras’s ability, at 72, to keep his business—and influence—strong, despite these headwinds.

It’s not unusual for Boras to enter the offseason as the agent for top-tier talent. His agency has a knack for targeting high-profile players even before they enter the draft, and he’s known for convincing established stars to leave their agents and sign with him, as he did with Alonso, Bregman, Burnes, and Snell in recent years. With the exception of players like José Altuve, most Boras clients aim to cash in on the open market’s true value.

In 2019, Boras represented three former first-round picks and had no trouble securing massive contracts for pitchers Gerrit Cole (nine years, $324 million with the New York Yankees), Stephen Strasburg (seven years, $245 million with the Washington Nationals), and third baseman Anthony Rendon (seven years, $245 million with the Los Angeles Angels). That winter, Boras’s clients netted $814 million—a record that helped his agency surpass $1 billion in deals.

Last winter, however, Boras had a tougher time. He was negotiating contracts for four major clients: former NL MVP Cody Bellinger, third baseman Matt Chapman, pitcher Jordan Montgomery, and Snell. But the landscape had changed. The pandemic had dampened owners’ enthusiasm for spending, while the expanded postseason reduced the urgency to build championship-caliber teams. The collapse of regional sports networks made things even trickier for teams like the Texas Rangers. Boras found himself trying to sell his players to owners who were more cautious and executives who were increasingly skeptical about long-term deals for aging players.

Examples of the challenges Boras faced were everywhere. Strasburg, riddled with injuries, made just eight starts during his new Nationals deal before retiring. Rendon has been frequently sidelined with injuries. Even Cole, despite being a high-performing ace, was hurt by an elbow injury this past spring.

“There’s definitely recognition that these kinds of deals don’t always work,” one executive noted.

By the time spring training started last year, Boras had yet to secure deals for any of his prominent free agents. Bellinger eventually signed a three-year, $80 million deal with the Chicago Cubs. Chapman, Snell, and Montgomery all took short-term, “pillow” contracts designed to set them up for future success.

The delays in signing and the lack of nine-figure deals led to industry chatter that Boras had overestimated the market’s appetite. Executives believed he failed to factor in the full impact of the television collapse and underestimated how much teams had already adjusted their strategies.

Despite this, Boras remained defiant, dismissing the TV situation as last year’s issue and asserting that teams were now fully aware of the next-generation distribution models.

This offseason, Boras faces new tests. Three days after the World Series ended, Cole informed the Yankees he would opt out of his contract’s final four years and $144 million. However, after a 48-hour standoff, the Yankees and Cole agreed to maintain the original deal. Rival agents chuckled at Boras’s attempt to force an opt-out, suggesting that his tactics were out of step with the current market.

But Boras’s reputation still holds sway. One rival agent, while admitting some frustrations with Boras’s methods, acknowledged that he’s one of the best in the business. “Andrew Friedman doesn’t win the World Series every year, and he’s one of the best at what he does,” the executive said.

At the GM meetings in San Antonio, Boras held his usual media briefings, where he delivered a blend of humor and metaphors to reporters. When discussing Snell, Boras joked that the “Snelling salts” had revived his market; when talking about Bregman’s championship pedigree, he said, “everything about him is AB-positive,” and when promoting Alonso, he quipped about the “bear market for power-hitting first basemen.”

As for Soto, Boras painted him as the magic behind every championship run, calling him “the magic Juan.”

While Boras’s clients often exist in a reality he creates, his influence over the market is undeniable. The story of Soto’s impending free agency will be the headline this winter, but how Boras’s other clients fare will be a better measure of his ongoing dominance in the baseball world.

And as the offseason unfolds, MLB executives remain eager to see how Boras will continue to shape the market. Even as teams like the Mets and Yankees fight for Soto, Boras’s influence remains as powerful as ever, leaving the baseball world waiting to see how the winter will unfold.