Presented By Cubs Insiders

Andre Dawson knows what it's like to be on both sides of Chicago's Crosstown rivalry.

Well, not really.

But he at least knows what it's like to wear a White Sox hat, even if he never played on the South Side.

Dawson tried on a White Sox hat one time in the middle of the 1986 season, just months away from his first foray into free agency. He was being connected to the Sox in trade rumors and was convinced once by a grounds crew member to put on a White Sox hat.

That one moment of fate helped lead Dawson to Chicago's North Side, where he won the National League MVP Award the next summer.

Let him explain:

“Year 10 when I was a free agent, I was being mentioned in rumors about a trade involving myself going to the White Sox for Daryl Boston. My name was mentioned and it was prior to my having 10-and-5 status. I met a guy that was on the grounds crew and he was a big White Sox fan. He had a Chicago White Sox hat on while he was out tending to the ground crew duties. 

“I walked over to him and said, ‘do you mind if I borrow your hat?’ and he said ‘no.’ And he said ‘you can keep it if you want it.’ I said ‘no, I don’t really want it.’ Anyway, I took that hat and I put it on and I can remember asking Warren Cromartie how I looked in this hat. Cro started laughing and said you know somebody is probably going to take a picture of you with this hat on.


“It didn’t even dawn on me that I was doing something inappropriate, I just wanted to see how I looked with the hat on. Well, as it turned out, they just didn’t appreciate that I was out on the field with the White Sox hat on. The trade never came to fruition. I wound up ending the season in Montreal, but Chicago, just the thought of Chicago, not the White Sox per se, but Chicago, I kind of think it had a ring to it.”

Dawson was granted free agency after the '86 season and inked a deal with the Cubs, where he spent the next 6 seasons.

"The Hawk" led the league with 49 homers and 137 RBI in 1987, taking home MVP honors for a last-place club.