Chicago Cubs: The end of an era for all involved
The decade was not kind to the Cubs who were synonymous with losing as they only managed two winning seasons during those years despite Grace being a constant, flagship player.
While Grace always maintained his intentions of finishing his career in Chicago, his relationship with the club became strained by the end of the 2000 season.
Legend has it, during batting practice on an August day at Wrigley Field in 2000 (the Cubs, of course, mathematically eliminated from the playoffs by the end of May), Grace retreated back to the dugout after taking his reps. He sat beside retired Cubs outfielder Bob Dernier and, just as he was known to do, lit up a cigarette and took a long, deep drag.
He took a minute, in thought, watching the smoke billow and dance in the warm summer wind around the dugout before letting out a sigh before glancing back at Dernier. “You know, I never smoke these things in the offseason. That’s what 13 years of being on the Cubs has done to me.”
The front office, tired of his smoking habits and, more importantly, his constant bickering with superstar slugger Sammy Sosa, decided not to re-sign Grace. He became a free agent.