The Boston Red Sox are no strangers to high-stakes negotiations, but their approach to potentially courting Alex Bregman in free agency has all the makings of a dangerous game. With Bregman’s agent, the ever-formidable Scott Boras, leading the charge, the Red Sox’s strategy could easily backfire, leaving the franchise in an unenviable position.

Bregman, the Houston Astros’ two-time All-Star third baseman, is set to hit free agency following the 2024 season. His track record as a cornerstone player, known for his stellar glove, consistent offensive production, and postseason heroics, makes him one of the most coveted players in the league. Naturally, such talent comes with a premium price tag, especially with Boras, the master negotiator, at the helm.

For the Red Sox, a team that has been criticized in recent years for their reluctance to retain homegrown stars or splurge on marquee talent, pursuing Bregman is both an opportunity and a potential pitfall. Their unwillingness to meet the asking price for stars like Mookie Betts and Xander Bogaerts has left fans skeptical of the team’s commitment to competing at the highest level. Adding Bregman could serve as a much-needed signal of intent, but only if they approach negotiations with a clear and decisive plan.

However, playing  chicken with Boras is a risky endeavor. Known for extracting record-breaking deals for his clients, Boras is unlikely to blink first. He will leverage every aspect of Bregman’s value, his leadership, clutch performance, and marketability, to secure a deal that could exceed $300 million. If the Red Sox balk at the price or attempt to lowball, they risk alienating not only Bregman but also their fan base, which is already wary of the team’s spending habits.

Furthermore, other suitors are waiting in the wings. Big-market teams like the Dodgers, Mets, and Yankees have deeper pockets and fewer hesitations when it comes to aggressive spending. If the Red Sox hesitate, they could easily lose Bregman to a rival, further diminishing their chances of contending in an increasingly competitive American League.

While the Red Sox have every right to be cautious with their financial commitments, the stakes in this game of chicken are too high. Losing out on a player of Bregman’s caliber could solidify the narrative that Boston is unwilling to invest in star power. If they are serious about returning to championship contention, the Red Sox must approach negotiations with boldness, transparency, and the willingness to pay the price for elite talent.

Bregman isn’t just another player; he’s a potential cornerstone. Playing games with Scott Boras might cost the Red Sox more than they can afford to lose.