Major League Baseball's front offices are accelerating extension talks with players two to three years before their first arbitration filing, targeting a narrow window when team control is maximum and agent leverage is still building. The Athletic identified five pre-arbitration candidates—Cleveland outfielder Chase DeLauter, Chicago White Sox catcher Sal Stewart, Cleveland catcher Drake Baldwin, Washington infielder Brady House, and Tampa shortstop Junior Caminero—as clubs test whether $40M to $80M guaranteed now avoids $120M+ post-arbitration deals later.

The math is clean. A player who reaches arbitration with two All-Star appearances and 140 games of service time commands eight-figure annual salaries through the process, then hits free agency at peak leverage. Teams are instead offering six- or seven-year pacts that buy out arbitration years and the first one to two free-agent seasons, locking in cost certainty before the player's third year in the majors. DeLauter, 23, posted a .289/.398/.527 slash line across 89 games in his debut season; the Guardians' front office has already begun informal conversations with his representation about a structure that would keep him in Cleveland through 2032. Stewart, a switch-hitting catcher with plus game-calling skills, fits the White Sox' rebuild timeline—his agent told league sources the club floated a framework starting at $45M over six years with escalators tied to All-Star selections and games caught.

The urgency comes from two directions. First, the current collective bargaining agreement's arbitration formula rewards early statistical spikes—a player who hits .280 with 25 home runs in his second year can argue comparables that push his first arbitration award above $8M, compressing the discount a team hoped to capture. Second, agents are holding tighter: Scott Boras and CAA Sports now routinely advise pre-arbitration clients to decline anything under $60M unless it includes a full no-trade clause, which eliminates the extension's chief advantage for the club. One AL general manager, speaking to the *Athletic* on background, said his ownership group approved $70M for a 24-year-old infielder only to have the player's camp counter at $95M, then pull the offer entirely when the team wouldn't add opt-outs. The player will now file for arbitration in 2027 with leverage reset.

Baldwin's case illustrates the risk calculus. Cleveland drafted him in the third round, he reached the majors in 13 months, and posted a .799 OPS as a rookie catcher—a position with persistent scarcity. His agent is Jeff Berry, who negotiated Adley Rutschman's debut extension at five years, $85M after Rutschman's first full season. Berry told MLB Network in late April he's not discussing anything for Baldwin under $75M, and the Guardians' payroll model caps pre-arbitration commitments at $65M unless the player accepts deferred money. The gap is $10M in present value, and neither side has moved in six weeks. If Baldwin files for arbitration after his second season—likely February 2027—and wins $6M, the extension window closes. The Guardians either pay him through arbitration and lose him at 28, or trade him to a large-market club willing to extend him at $110M+.

What to watch: the July 31 trade deadline becomes the forcing function. Teams out of contention will surface these pre-arbitration names in trade talks, testing whether a contender pays two top-hundred prospects plus takes on the extension obligation. The Rays have done this twice in three years—trading pre-arb controllable talent to the Dodgers, who immediately extend them. If DeLauter or Stewart changes hands by August, the acquiring club will announce an extension within 72 hours; it's the only way the trade makes financial sense. Also watch the December Winter Meetings: agents leak extension offers to reporters to create competitive pressure, and every declined offer becomes a public comp for the next negotiation.

The teams moving fastest are the ones who've already paid the arbitration premium once and don't want to repeat it. Cleveland lost José Ramírez leverage in his first arbitration year and ended up paying $26M annually after he reset the third-base market; the front office has since signed three pre-arb extensions in four years, none above $55M, and all are outperforming their AAV.