Because if he can pair productivity and health, he will easily surpass $100 million and be a good bet to blow past $200 million. Jeff Passan » Inside the transformation of Steinbrenner Field »Jarren Duran, OF, Boston Red Sox: He was originally on the $200 million list, but his age is a complicating factor. Gilbert is the quintessential modern pitcher, and with $200 million now the standard for true aces, he qualifies. The largest contract ever given to a pitcher was Yoshinobu Yamamoto's 12-year, $325 million deal in the 2024-25 offseason. Even then, Henderson needs more years of consistent quality before he can be looking at $600 million, let alone $765 million.