33. Jeff Fassero

The journey of Jeff Fassero is one of the most remarkable stories of perseverance in modern baseball history. Selected in the 22nd round of the 1984 draft by the St. Louis Cardinals, the left-hander spent a grueling seven years grinding through the minor leagues, occasionally wondering if his big-league dream would ever materialize. By the time he finally made his major league debut with the Montreal Expos in 1991, he was already 28 years old. Yet, far from a late-career afterthought, Fassero quickly evolved from a reliable left-handed reliever into one of the most dominant, high-leverage starting pitchers of the mid-1990s NL East.

His transition from the bullpen to the starting rotation ahead of the 1993 campaign completely unlocked his potential. Utilizing a deceptive, late-moving slider and a highly effective splitter, Fassero established himself as a frontline workhorse. He paced the rotation with a stellar 12-5 record and a microscopic 2.30 ERA across 23 starts, helping lay the groundwork for Montreal's legendary run the following year. During the star-crossed 1994 season, he remained a model of efficiency, going 8-6 with a 2.99 ERA over 138.2 innings to anchor a rotation that carried baseball's finest record before the strike cut the season short.

While the front office systematically dismantled the roster in the strike's aftermath, Fassero remained a steady, competitive anchor in Quebec. His absolute masterpiece in an Expos uniform materialized during the 1996 campaign. He completely paralyzed National League hitters, hurling a career-high 231.2 innings and logging 15 victories with a sharp 3.30 ERA. He racked up 222 strikeouts—the fourth-most in the Senior Circuit—to earn a well-deserved ninth-place finish in the National League Cy Young Award voting.

Knowing they would be unable to meet his contract demands as free agency loomed, Montreal traded the veteran lefty to the Seattle Mariners in October 1996 in a multi-player swap.

With Montreal, Fassero played in 231 games (107 starts), posting a 58–48 record, 3.20 ERA, and 1.21 WHIP. He pitched 885.1 innings, with five complete games, three shutouts, and 750 strikeouts, achieving a 125 ERA+.