Boles graduated from Leo Catholic High School in Chicago in 1966, and Lewis University, Romeoville, Illinois, in 1970.

White Sox skipper Tony La Russa wanted Boles to be Leyland's replacement, but Ken Harrelson, newly named the club's director of baseball operations, hired Doug Rader instead.

Meanwhile, former White Sox executive Dave Dombrowski (also forced out of the organization by Harrelson) had moved on to the Montreal Expos, where he eventually became general manager.

At the end of the 1991 season, Dombrowski was recruited by the National League's new expansion team, the Florida Marlins, to become their first general manager.

However, during the offseason, then-Marlins owner H. Wayne Huizenga decided to sign several marquee free agents to make a run at the World Series.

In addition to Gary Sheffield, Jeff Conine, Édgar Rentería, Robb Nen and Kevin Brown, among others, who were already with Florida, the Marlins signed free agents Alex Fernandez, Moisés Alou and Bobby Bonilla—then named Jim Leyland, highly successful with the small-market Pirates (with three National League East Division titles from 1990 to 1992), as manager.

The Marlins also were undergoing massive front-office changes, with Huizenga's successor as owner, John W. Henry, selling the team and Dombrowski leaving to become president of the Detroit Tigers.