Rita Guy

Kevin William Heenan
3 min readSep 7, 2022
Caffrey in his khakis

Confused on where I’m going and how I got here, I often run it back several decades and stir in the subtle reminder that life is OK. The following then serves enough reassurance — I’m where I’ve always dreamt.

In the fall of 6th grade, I sat at a banquet to honor an erratic football season. And as I reached for the sure thing, a bread roll, an arm reached for me. Except, I was also a wild card, at least when it came to choosing St. Rita High School.

The arm belonged to Chuck Caffrey, a consummate yuppie (by southside standards) and husband to Denise, owner of the luxury reconsignment studio, McShane’s Exchange. He was also dad to 7th grader, Doyle, and ‘the’ biggest booster for, at the time, an overlooked St. Rita. And though he wasn’t a stranger per se, I knew him for just one little league (baseball) summer.

I found his dugout only because his assistant (coach) was a family friend and convinced, via nepotism, that my average arm and weak bat were worth the rattle. And rattle Caffrey’s batting cage (which held a future division one player and current 6th grade superstar) I did.

After draft night, he didn’t say my name again until the sixth game. Likely because, in a moment of 1st place, I heeded his (steal) sign, took third, then home (on a sac fly), and we beat a great team coached by a big jerk.

My dad knew Caffrey, or knew he smoked expensive cigars in the south end zone during football practice. And maybe dad was currying favor, or Caffrey was blowing smoke, or both, but under center (I was just as mediocre a QB) I paid no mind to steam coming from the nose tackle.

Instead, all eyes were on Caffrey, now covered in Cuban Cohiba, as I grew akin to him and his wonders. Wonders of rugged khakis neatly draped over grey New Balance (navy ones were in his BMW convertible), and coupled with a sweater-thick St. Rita sweatshirt and a pristine puff, it was certain this man was privy to the good life.

Raised catholic on the southside of Chicago, if Jesus was gold, a Chicago Catholic League education and its respective athletic prowess were frankincense and myrrh. And though the aforementioned St. Rita could afford a Toyota life, steady and safe, if I wanted a shot at a BMW one, savvy and splendid, Caffrey was Christ.

I put the bread down and stood up to shake Caffrey’s hand. By now, tablemates were just as hungry for why Caffrey handed me his same sweater-thick ‘St. Rita’, only a few sizes smaller, leaving me with just “Good season, Kev”. But reflecting back, those New Balances, striding away, said “Good life.”

“You’re a Rita Guy now,” someone said.

Little did I know, I’d be a Rita Guy for life.

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