Yankees Choice Between Top Free Agent Outfielders May Depend on an MLB Agent
The Yankees face a series of critical decisions regarding their outfield this offseason. Chief among them is whether to commit to one of the top free agents to fill a key spot. Beyond that, a host of moving parts complicates the picture. Money and contract length are major factors, and the team’s direction may ultimately hinge on how influential agent Scott Boras chooses to play his cards this winter. Once again, Boras is positioning Cody Bellinger as a superstar-level free agent, aiming for a massive contract.
Scott Boras’s representation of Cody Bellinger complicates things for the Yankees. They admire Bellinger but are reluctant to commit to a lengthy contract. Last year, the Yankees secured Bellinger from the Cubs for a bargain price of five million dollars and Cody Poteet. However, this time Boras is seeking a far bigger payday for his client. While Boras and his patient negotiating style have sometimes cost his clients in the past, Bellinger is expected to land a lucrative deal somewhere. Yankees GM Brian Cashman has made Bellinger a priority, but he has also been clear that the team will not go beyond its comfort zone in contract length. Bellinger’s last significant deal was a three-year deal for $80 million. Boras now wants at least double the years and more than twice the money. If the Yankees are priced out, it will be because they’re prepared to pivot to their backup plan.
Kyle Tucker, still in his prime, is poised for the largest contract of his career. While some may doubt his value after a relatively average season, the current market tells a different story. Devin Williams and Dylan Cease both landed lucrative, multi-year deals despite less-than-stellar years. If the Yankees are going to invest in a player for seven or more years, Tucker is the logical choice; he’s younger than Bellinger and fits both the present and future needs of the team.
Trent Grisham is likely gone after this year, Aaron Judge is spending less time in right field, and Giancarlo Stanton is locked in as a designated hitter. The Yankees’ pursuit of Tucker signals they don’t see Jasson Dominguez or Spencer Jones as ready solutions. Tucker could anchor left field now and eventually move to right as Judge transitions out of the outfield. This strategy would allow the Yankees to use Dominguez as a trade chip and position Jones as the future in center field once Grisham departs.
One often overlooked factor is the agents’ negotiating styles. Casey Close, who represents Tucker, is generally easier to work with than Scott Boras. The Yankees have a history of tough, often unfavourable negotiations with Boras' clients. He’s known for driving up prices, refusing to compromise, and starting bidding wars even when there isn’t much competition. If Boras overprices Bellinger or asks for too many years, there may not be many serious bidders left.
In contrast, while Close will still seek a strong deal, negotiations with him are less likely to spiral into a bidding war. In the case of Bellinger, the Yankees may be bidding against themselves, as Boras rarely yields. Despite Hal Steinbrenner’s friendship with Boras, the agent has never given the Yankees a break. Ultimately, Boras’s tactics could determine the fate of both outfielders, even though he only represents one.
