Chicago Cubs: A history of notable Home Run Derby performances

Chicago Cubs: 1987 – Andre Dawson defeats Ozzie Virgil

The winter of 1987 saw Dawson sign a one-year deal with the Cubs for a mere $650,000. Outside of Chicago’s frivolity, it became a contract that would change the course of how money moved hands and arbitration would play an essential role in future contracts.

By season’s end, Dawson had smashed 49 long balls for the Cubs. Rewinding to the Midsummer Classic weekend, he was chosen as one of four players to participate in the then third annual Home Run Derby.

In the first few years of the derby itself, there was a lot of experimentation. Trying to figure out the best model for the entertainment, in 1987, there existed two “innings” or, more simply, rounds. Each of the participants received five outs per “inning.”

Unfortunately, it will go down as one of the most blasé derbies in MLB history. A total of eight home runs were hit—Dawson, who won the whole thing, hit four bombs. Virgil finished second with two, and both George Bell and Mark McGwire each ended the mundane event with a single home run. Still, Dawson became the first official Cub to win a derby, so he finds himself atop this list.