Chicago Cubs: A history of the beloved ‘W’ flag on the North Side

One of my favorite rituals after any Chicago Cubs victory, whether in town or on the road, is watching countless fans fly their respective ‘W’ flags.

My wife ordered two new ‘W’ flags that arrived this week in the mail. She was thinking the  Chicago Cubs would be cruising in postseason right about now. I had abducted the larger 3×5 ‘W’ flag and hung it my office at work.

My son and daughter came into the room to see what package had arrived in the mail as I pulled out the two new flags. They looked disappointed as they knew the Cubs were not in the postseason. To get their minds off the Cub’ dubious demise, I asked them, “Do you know what the ‘W’ stands for?”

“Wrigley Field,” my 10-year old daughter said quickly.

“No… it stands for win,” my teenage son said.

As I began to unfold the flags I told them the history of the ‘W’ as I had learned it over the years.