As Major League Baseball’s offseason continues to unfold, two of the sport’s most prominent free agents—first baseman Pete Alonso and third baseman Alex Bregman—remain unsigned, with their markets developing slowly and deliberately. According to Jeff Passan of ESPN, Alonso is currently waiting for a team to “step to the forefront,” signaling that while interest exists, no club has yet taken the decisive leap needed to secure one of the league’s premier power hitters. Passan describes Bregman’s free agency in almost identical terms, suggesting that both players are navigating a similarly cautious, evolving market.

It is not a coincidence that Alonso and Bregman’s situations mirror each other. This offseason, the two stars are linked in multiple ways—financially, competitively, and strategically. Both players are represented by agent Scott Boras, whose negotiation style is known for patience, precision, and a willingness to extend free agency deep into the winter in order to maximize value for his clients. As a result, teams eyeing either player must be prepared for a deliberate, methodical process rather than a quick resolution.

One organization that has emerged as a potential focal point for both players is the Chicago White Sox. According to multiple reports, the Sox could represent the most credible non-Mets threat to sign Alonso, signaling a surprising aggressiveness from a club in transition. Chicago has reportedly expressed interest in adding a middle-of-the-order bat, and Alonso—one of the most consistent home run producers in baseball—would instantly reshape their offensive identity. Simultaneously, the Sox have explored the possibility of re-signing Bregman, who would bring veteran leadership, postseason experience, and elite on-base skills to their infield.

The possibility of the White Sox pursuing both stars underscores the unique nature of the current free-agent landscape. Teams across the league are evaluating how much star power, leadership, and long-term upside they need to remain competitive—not just next season but for several years to come. Both Alonso and Bregman are cornerstone players, capable of changing a franchise’s trajectory.

Meanwhile, in New York, the Mets remain firmly in the picture for Alonso. President of baseball operations David Stearns has emphasized repeatedly throughout the offseason that the team would “love to retain” their longtime slugger. Alonso, a homegrown star and a fan favorite, represents both a marketing icon and a central piece of the Mets’ lineup. However, Stearns has also maintained that the organization must operate with discipline and avoid making decisions driven solely by emotion or public sentiment.

Alonso, whose power numbers and durability have made him one of the league’s premier first basemen, is expected to command a significant long-term commitment. His track record—highlighted by 40-plus homer seasons, remarkable consistency, and a strong clubhouse reputation—makes him a fit for numerous competitive teams. Yet his free agency remains quiet, suggesting clubs may be waiting for clarity on price, contract length, or broader market movement before fully engaging.

Bregman’s market, too, has been slower to accelerate than initially anticipated. Once the cornerstone of the Astros’ infield, Bregman brings an impressive résumé: multiple All-Star selections, elite plate discipline, and postseason heroics. But as with many top-tier free agents, teams must weigh his long-term projection, especially as he enters his 30s. His versatility and leadership, however, ensure that he will be viewed as a premium option for clubs seeking stability at third base.

Free agency in recent years has increasingly become a waiting game, especially for players at the top of the talent pool. Teams often hesitate to make early aggressive offers, hoping the market will clarify itself or other dominos will fall first. Meanwhile, agents—particularly Scott Boras—frequently encourage their clients to remain patient, believing that the strongest offers typically emerge later in the offseason as front offices refine their priorities.

What makes this offseason especially intriguing is the mirrored trajectory of Alonso and Bregman. Both are high-impact players represented by the same agency, both have significant financial expectations, and both have yet to draw a clear frontrunner in their respective markets. Their decisions will shape not only their own futures but also the strategies of teams still navigating roster construction.

For the Mets, the outcome of Alonso’s free agency may define their offseason. For the White Sox, potential pursuits of either—or both—players would signal a bold commitment to retooling. For other clubs quietly monitoring the market, the right moment to act may still be ahead.

As December turns to January and spring training inches closer, the baseball world waits to see which organization will “step to the forefront.” Whether Alonso returns to Queens, Bregman stays with Houston, or one or both find new homes, their eventual signings are expected to send ripples across the league.

Until then, two of baseball’s biggest names remain at the center of one of the offseason’s most compelling storylines.