As pitchers and catchers report to Spring Training for 2024, the baseball free agency cycle continues to deliver high-impact moves, even this late in the offseason.
Free agent third baseman Alex Bregman signed a four-year, $120 million contract with the Boston Red Sox on Wednesday. The 30-year-old player, who spent his entire career with the Houston Astros, declined an identical offer from the Chicago Cubs as well as a six-year, $170 million contract from the Detroit Tigers. The deal also includes two player opt-outs, allowing Bregman to re-enter free agency if he chooses.
First baseman Pete Alonso re-signed with the New York Mets in a move many viewed as a delayed certainty. He has signed a two-year, $54 million deal that includes an opt-out after the first year, allowing him to re-enter unrestricted free agency. This contract positions him alongside Freddie Freeman of the Los Angeles Dodgers as the second-highest-paid first baseman in Major League Baseball (MLB), with an annual salary of $27 million. Vladimir Guerrero Jr. of the Toronto Blue Jays currently holds the top spot at $28.8 million per year.
Alonso and Freeman are represented by agent Scott Boras, who manages dozens of high-profile baseball players and is known for maximizing their earnings in negotiations. Boras has earned his clients the nickname “Boras Guys” due to his reputation for squeezing every last cent out of MLB front offices.
However, Boras’s strategies may no longer be as effective as they once were. While his negotiation techniques remain consistent, the landscape around him has evolved. Earlier in the offseason, the Mets offered Alonso a seven-year, $157 million contract, which was more than $100 million greater than the deal he ultimately accepted. Boras convinced Alonso that he could potentially secure a more lucrative contract elsewhere, but that did not happen. Although the opt-out in Alonso’s contract gives him a chance to earn more in free agency in 2026, if he ends up sticking with the current contract and missing out on the money he could have secured, it would represent a significant misstep for both him and Boras.
Bregman was unable to secure the initial amount of money he desired, so including opt-out clauses became essential in his new deal with Boston. This approach allows him and his agent, Boras, to pursue the compensation they seek, even if it means giving up a significant amount of guaranteed money.
This winter isn’t the first time Boras’s management style has led to controversial contracts for his clients. The offseason of 2024 was particularly tumultuous for Boras, who represented several top free agents such as Blake Snell, Jordan Montgomery, Matt Chapman, and Cody Bellinger. All were coming off strong seasons and were expected to find new teams without much difficulty.
Boras, confident in his negotiating approach, set high price tags for his players. However, he faced widespread rejection, resulting in a standoff that extended well into the offseason. Jordan Montgomery eventually signed with the Arizona Diamondbacks but did not finalize his contract until a few regular-season games had already been played.
This issue reflects a generational shift in baseball negotiations. For years, Boras had the upper hand over front office executives, often providing valuable insights that highlighted the worth of his clients. He effectively utilized advanced metrics to demonstrate why teams should offer more money.
Unfortunately for Boras, as the baseball community has become more sophisticated, and analytics have developed rapidly over the past decade, teams are now better equipped to evaluate player value accurately in the open market. As more information becomes available, it can diminish the small advantages Boras previously enjoyed.
If Boras remains stubborn in his negotiation tactics, it may lead to longer wait times for his clients to sign contracts and ultimately result in financial losses for them—contrary to the very reason they hired him.
By Anders Pryor