35. Moises Alou

This transaction stands out as one of the most notable footnotes in franchise history. In August 1990, the Montreal Expos traded pitcher Zane Smith to the Pittsburgh Pirates for Moises Alou, who was initially listed as the "Player to be Named Later." At that moment, Alou was a promising but inexperienced prospect, having only played two major league games. By the time he left Montreal six years later, he had become widely known and had secured his role as the focal point of an exceptional, world-class outfield, guided directly by his father, legendary manager Felipe Alou.

Alou’s rise in Montreal showcased exceptional bat speed and physical resilience. After recovering from a severe ankle injury in 1993 that ended his season, he returned in 1994 to deliver a standout performance. He dominated National League pitching, hitting .339 with 31 doubles, 22 home runs, and 78 RBIs in just 107 games. His outstanding offense earned him his first All-Star appearance, a Silver Slugger Award, and a third-place finish in NL MVP voting, helping the Expos maintain baseball’s best record before the strike brought play to a halt.

Far from a single-summer peak, Alou remained a premier, high-leverage force in the middle of the order. He backed up his breakout campaign by hitting .273 with 21 home runs in 1996, helping guide a transitioning Expos roster to a highly competitive 88-win season. He possessed a beautifully balanced right-handed swing and a rare knack for delivering in critical situations, routinely punishing pitchers who dared to challenge him with runners on base.

However, as was common during this period of Montreal baseball, the financial constraints of a small-market team ended his tenure early. Knowing they couldn't compete with the high offers from free agency, the team saw their star outfielder leave after the 1996 season. Alou then signed with the Florida Marlins, contributing immediately to their 1997 World Series victory, and went on to have an outstanding 17-year career in Major League Baseball.

Alou played 594 games with the Expos, amassing 598 hits, 122 doubles, 84 home runs, and 335 RBIs. He stole 51 bases and posted a .292/.354/483 slash line with a 124 OPS.