$21,026 on New York Yankees - Boston Red Sox — MLB

Tracked on tail.bet, the New York Yankees account for 21 high-roller wagers totaling $381,675, with bettors posting a 56.2% win rate across settled positions. The largest captured bet staked $62,272 on a Yankees single against Baltimore, returning $90,294. The dataset skews heavily toward parlay construction—14 of 21 bets bundled Yankees selections into multi-leg tickets—positioning the franchise as a recurring component in complex combinations rather than a standalone play.