The New York Yankees continue to drive early MLB offseason moves, and the newest wave of rumors now centers around a hypothetical Steven Kwan trade that gained momentum after James “Jomboy” O’Brien broke down why it works. The concept drew interest because it fits several long-term needs for the Yankees and pushes the Guardians outfield into sharper focus. O’Brien details how adding the contact hitter brings bat-to-ball skill, elite defense, and cost control to a club looking to refine its approach at the plate.

Jomboy outlined his reasoning on the Talkin Yanks podcast, highlighting an outfield mix he believes could shift the Yankees identity. The podcast’s account later posted the clip on its official X (formerly known as Twitter) account, showing him explain why his profile matches what the roster needs as the club looks for on-base skill and elite defense. The segment spread quickly across the league.

“Jomboy really likes the idea of a Yankees outfield that features Aaron Judge, Cody Bellinger and Steven Kwan”

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The post quickly fueled stronger Yankees rumors as talk around the team grew about whether the front office would pursue an MLB offseason move aimed at adding more balance at the plate. That conversation only intensified after another early October exit in which the Yankees were beat 3-1 in the ALDS by the Toronto Blue Jays. His elite contact rate, four straight Gold Gloves, and steady on-base skill make him a rare fit for a team long built on power. His 2025 season with the Guardians underscored that value, producing 170 hits, 21 steals, and another standout defensive campaign.

For the Guardians outfield, an eventual move could make sense if the front office seeks additional offense after ranking near the bottom of MLB in runs per game. Their strong pitching foundation creates room for a roster rebalancing move. A Kwan trade would return significant value, and the Yankees remain a logical partner, potentially targeting the 28-year-old left-handed contact hitter to bring more reliability and balance to their lineup.