Being a baseball fan in Chicago is like being in a bad marriage. You keep showing up, keep believing, and somehow keep getting your heart stomped on. We finally got a couple of miracles in this lifetime, Sox in 2005, Cubs in 2016. That is more than most of our parents and grandparents ever got. They lived and died waiting for parades that never came.
Just a typical Chicago guy juggling fatherhood and bachelorhood. I’m an old trading floor broker who drives around in Chet the Ford Lemon and lives by the river. Most of these stories are life lessons meant to make you laugh, cry, and think. The “Chalkboard” is a daily post scribbled on the blackboard in my kitchen ... it has become my morning ritual, a bit of therapy and a small win to start the day. All Chalkheads are welcome to ride along.
Monday, September 8, 2025
September 7th, 2025
On the South Side, the Sox are just about to put us out of our misery. Up north, the Cubs still have “a chance,” but don’t kid yourself, being a Cub fan just means your disappointment shows up in September instead of June.
Then there are the Bears... God help us.
Monday night kicks off another season of Monsters of the Midway mythology, and it’s been forty years since they were kings. As of today, they’re technically “in the hunt” for a Super Bowl. By Tuesday morning, that hunt will look more like a crime scene.