Scott Boras' World Series doesn't come until the MLB GM meetings and beyond. From there, Boras takes center stage, helping the players he represents land the richest contracts in baseball. He's done this time and time again – most notably with Juan Soto last winter, who signed a $765 million contract – and has more opportunities to come in 2025-26.
Boras works off commission, which normally sits around 5 percent of the total contract for baseball agents. It's possible Boras' rate is a little higher given his name brand, but at that five-percent market, he will receive an estimated $38,250,000 over the course of Soto's contract.
Baseball's foremost super-agent will not make his Soto money this winter, as it's unlikely any free agent touches the Dominican star's history-making deal. However, Boras does represent several star players set to receive new deals that should shake the sport to its core. That's great news for said players, but bad news for some of the organizations negotiating with him.
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4. Baltimore Orioles
Yes, we'll start as we promised. The Baltimore Orioles just signed Samuel Basallo to a contract extension a mere days ago, but if they to plan on committing to this young core, shortstop Gunnar Henderson should be next. Henderson was asked earlier this week if he'd be open to an extension, and didn't disappoint.
“I mean, if they bring it there, then I’ll definitely look at it with my team and be happy to look over it,” Henderson said.
Henderson is signed through the 2028 season so there is no huge rush from Baltimore's perspective. However, Mike Elias would rather get a deal done sooner than later. The longer the Orioles wait to extend Henderson, the more his price could go up. Unfortunately for the O's, Henderson is represented by Boras, an agent who typically takes his top clients into free agency with the promise of more money if they're willing to change locations.
3. San Diego Padres
The San Diego Padres went all-in at the MLB trade deadline in an attempt to take down the Los Angeles Dodgers in the NL West. Whether or not that goal is successful is irrelevant to their offseason, which will be headlined by free-agent starting pitcher Dylan Cease.
Cease is having a down year by his standards – he is just 6-7 with a 4.71 ERA. That is a steep drop from the NL Cy Young candidate, and it could cost him this winter. Yet, we wouldn't put it past Boras to increase Cease's value based on the not-so-distant past. He finished fourth in Cy Young voting just last season, and second back in 2022.
Even should Cease's price drop, it doesn't change the fact that the Padres long-term financial situation isn't great. The widow of the late Pete Seidler sued her brother-in-laws over assets, which includes some control of the team. While John Seidler has since been approved as Padres control person, his financial flexibility could be tested at any given moment.
2. New York Mets
Boras has a great working relationship with the Mets, in part because Steve Cohen isn't afraid to spend money. Sure, they disagree on valuation every now and then, but Cohen's money is going directly into Boras' pocket thanks to contract handed out to Juan Soto and Pete Alonso.
Speaking of Alonso, he could be a free agent again this winter. Alonso signed a two-year, $54 million contract this past winter, but he has a player option after this year. Given the lack of big bats in the free-agent market, it makes a lot of sense for Alonso to opt out if he has any inclination he can get a long-term deal.
Alonso made the NL All-Star team again this season, and has an OPS of .844, his highest since 2022. While the slugger isn't technically in a prove-it year due to the player option, he has a lot to gain by playing well down the stretch and leading the Mets on a postseason run. Alonso is a hero in Queens. It's why they re-signed him last winter. However, David Stearns took a gamble giving a short-term deal with an opt-out. Now, it could backfire and force the Mets to pay up.
1. Boston Red Sox
The Boston Red Sox wanted Alex Bregman, and they got Alex Bregman. Boston won a bidding war with the Detroit Tigers, Toronto Blue Jays and more for Bregman's services this winter. It has paid off for them and then some, even if it led to radical changes like trading Rafael Devers to the San Francisco Giants.
Bregman was injured for a solid portion of the season, but when healthy he's been solid. When healthy, Bregman has a batting average a shade over .300 and a .911 OPS. Boston can't ask for much more than that, especially from a player who was coming off a down season by his standards in Houston.
Craig Breslow invested in Bregman, signing him to a three-year, $120 million contract. However, Bregman is just one decision away from leaving the remaining money on the table. Bregman is one of the best defensive third basemen in baseball to this day despite his age, and is open to transition to first or second base in the future if called upon. He is an fantastic clubhouse presence for a young Red Sox team in need of leadership.
The Red Sox cannot afford to lose him, and Boras knows that. They better prepare to pay up.