Padres’ perfect trade offer for Yankees’ Jazz Chisholm Jr.

The San Diego Padres have emerged as a sleeping giant in the National League West, quietly assembling a roster capable of challenging for a Wild Card spot and potentially more. With their recent trade deadline acquisitions and farm system improvements, the Padres front office appears ready to make a splash in the 2025 offseason. One name that continues to circulate in baseball circles is New York Yankees infielder Jazz Chisholm Jr., the dynamic dual-threat performer who has become one of the most electrifying players in the Bronx. At just 26 years old, Chisholm Jr. represents the type of generational talent that doesn’t hit the trade block often, but when GM A.J. Preller smells opportunity, he’s historically been willing to pull the trigger.

Chisholm Jr.’s 2024 season was nothing short of historic. The Bahamian-born infielder became only the third player in Yankees history to record 30 home runs and 30 stolen bases in a single season—a distinction previously held by only legends like Mickey Mantle and Willie Mays. His combination of power and speed is virtually unparalleled in today’s game, giving the Yankees an elite player who operates on both sides of the ball. Last season, he posted 24 home runs and 40 stolen bases while slashing .273/.306/.500 across 147 games, showcasing the kind of complete offensive package that wins games down the stretch and in October.​

However, for the Yankees—a franchise perpetually chasing a World Series title—Chisholm Jr. may soon become expendable if ownership grows impatient with the team’s postseason underwhelming performance. The Padres, meanwhile, have the prospect capital and veteran depth pieces to construct a compelling offer that addresses New York’s needs while bringing a transformational talent to San Diego.

Building the Framework for Jazz Chisholm Jr.

The Padres’ interest in Chisholm Jr. isn’t frivolous conjecture—it’s rooted in organizational philosophy. Preller has consistently shown a preference for acquiring dynamic, controllable talent under reasonable contracts, particularly players who fit the mold of the modern competitive window. Chisholm Jr. agreed to a one-year, $5.85 million deal to avoid arbitration in January 2025, but is now seeking a long-term extension that would significantly increase his salary in arbitration (projected at no less than $11 million for the 2026 season).​

The Yankees face a critical juncture. With Juan Soto’s massive contract consuming significant payroll flexibility and Aaron Judge’s aging curve looming on the horizon, Chisholm Jr. represents expensive young talent that competing organizations would covet. San Diego, conversely, is positioned to absorb his future contract demands while simultaneously offering the Yankees a compelling haul of young, MLB-ready and prospect-level talent.

The three pieces the Padres should offer—Ramón Laureano, Jeremiah Estrada, and Kash Mayfield—form a trifecta that addresses the Yankees’ immediate needs and future trajectory.​

San Diego Padres’ Trade Proposal for Jazz Chisholm Jr.

Padres Receive:

• 2B Jazz Chisholm Jr.

Yankees Receive:

• OF Ramon Laureano
• RHP Jeremiah Estrada
• LHP Kash Mayfield

Laureano, a 30-year-old outfielder with a championship pedigree, provides the Yankees with immediate depth in right field and a veteran presence on the bench. After settling in with the Baltimore Orioles, Laureano has been a pleasant surprise in 2025, slashing .281/.350/.517 with 24 home runs and 76 RBIs in 441 at-bats. His above-average .867 OPS indicates he’s still capable of contributing at an elite level, particularly as a platoon option against left-handed pitching. For a Yankees team that has struggled with offensive consistency in corner outfield positions, Laureano provides a seasoned professional who knows the American League landscape intimately.​

Estrada, the Padres’ talented relief pitcher, brings proven strikeout stuff to the Bronx bullpen. In 2024, the 27-year-old compiled a 2.95 ERA across 62 appearances with 94 strikeouts in just 61 innings of work. More impressively, from May 23-28, 2024, Estrada etched his name into MLB history by striking out 13 consecutive batters—a record since the expansion era. His 3.45 ERA in 2025 demonstrates his ability to perform at the major league level consistently, offering the Yankees a controllable arm under team control through the 2027 season. The Yankees’ bullpen has been a perennial weakness, and Estrada’s mid-90s fastball and plus slider combination would address that glaring need.​

Mayfield, the Padres’ prized 2024 first-round draft selection (25th overall), represents the top prospect of this package from a future-oriented standpoint. The 20-year-old left-handed pitcher possesses big league potential, standing 6’4″ with an ideal starter’s frame and an aesthetically pleasing, low-effort delivery that of a future front-line starter. In his 2025 action at Single-A, Mayfield posted a 3.12 ERA across 19 games at Low-A Lake Elsinore Storm, striking out 88 batters in 60.2 innings. His advanced command for a pitcher his age, combined with a plus changeup (one of the best in the 2024 draft class), positions him as a potential No. 3 starter in the major leagues by 2027.​

This trade framework makes profound sense for both organizations. The Yankees receive three distinct value propositions: an immediate contributing veteran outfielder, a controllable relief arm for their beleaguered bullpen, and a high-ceiling prospect pitcher with projection to star at the major league level. The Padres, meanwhile, acquire a generational talent—a player capable of anchoring their franchise for the next decade while delivering the kind of dual-threat production that elevates winning teams into legitimate October contenders. For San Diego, this trade accelerates their competitive timeline while maintaining organizational depth. For New York, it represents a calculated bet-hedging strategy in a championship-or-bust window.

The pieces are in place. The question now is whether Hal Steinbrenner and Brian Cashman have the organizational courage to reshape the roster around Chisholm Jr.’s game-changing skill set.

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