My Coworker's Mom's Ex Boyfriend: A Bookie for the Mob

I went out to lunch during a work day, and I saw one of my coworkers sitting in a booth.  He eats there just about every Monday through Friday.  Even if I really wanted to sit by myself and read about Chicago sports and text jokes to my friends, the right thing to do was go sit by him.  I just didn't feel like hearing him bitch about work because getting out of the office for lunch is a time to think about anything but the office.  Actually, he may have been thinking, "Oh crap.  Here comes Dr. Ken to come saddle in here and make annoying observations for his stupid blog."  That's entirely possible.  Sometimes I wish people could be honest with each other and just ask, "mind if I join you?" and the other person could respond either way without hurting anyone's feelings.

So this guy was telling me how excited he was to go to the Kentucky Derby with some friends to drink a ton and bet a bunch of money on little men riding on horses running around in a circle.  He really likes gambling.  He spends every few Saturdays at a race track near his house drinking three dollar beers and betting every race until the joint closes.  He really seems to know his stuff, but then again, gamblers never seem to tell you about the times they lost.

I asked him how he got so knowledgeable about betting the ponies, and apparently his mom's ex boyfriend would take him to the track when he was a kid, starting when he was around eleven years old, and schooled him on how to research and pick a winning bet.  The mom's boyfriend used to be a bookie for the mob, but he had left that life behind to drive a taxi cab.  Still, it was still strange that he drove a taxi in the suburbs but somehow always had giant wads of one hundred dollar bills wherever he went.  I guess he was a pretty great guy, and he took my coworker out for a steak dinner and gave him two hundred bucks for his birthday every year.  Even after his mom and the guy broke up, this dude continued to take him out for his birthday dinner until my coworker was around 19-years-old.  That is around the time his health started failing and he soon passed away.  I think he was a little bit older than the mom.

I asked why it didn't work out, and he said, "I don't know because he was a really great guy.  I think my mom was just too much to deal with."

I said, "So the ex (but probably current) bookie for the mob wasn't the problem in the relationship; your mom was."

"Yeah, pretty much," he said, finishing the last few bites of his omelette and getting a look at his check.