If you learn anything with age, it’s that life can be a funny old dog, chock full of unexpected ironies.  For me, last week’s New York City mayoral election drove that lesson home once again.

Those of you who know me or read my blog are aware that my first job out of college more than thirty years ago was working for Andrew Cuomo.  Among my duties was driving him to meetings. Andrew had an orange Ford Bronco with side mirrors the size of a keg of beer. The thing seemed to have the wingspan of a pterodactyl.

I can still remember praying that I wouldn’t decapitate a pedestrian or side swipe another vehicle as I raced through crowded, rush-hour Manhattan streets with Andrew in the passenger seat urging me to punch the gas while he talked on the phone.  (A car phone back then was a huge flex.)

One sunny summer day in 1992, I drove Andrew from our office on 33rd Street uptown to Trump Tower. Andrew had a meeting with New York’s most famous real estate developer, Donald Trump. While Andrew went upstairs, I stayed with the Bronco out front.

Maybe 45 minutes later, he strode quickly out of Trump Tower and jumped into the truck.

“How did it go?” I asked.

He smiled as he grabbed the phone. “Trump wants me to run for mayor next year. He said Dinkins is done and I’m the guy for the job,” he answered.

My first thought was it might be a bit complicated for Andrew to run for mayor while his father was governor. But I was a very wet-behind-the-ears kid, and he was a legendary political wunderkind, having directed his father’s campaigns while still in college. I couldn’t resist asking, “You going to do it?”

Andrew laughed and shook his head as he reached for the phone. I don’t remember his exact words, but as he dialed he made it clear that he didn’t think much of Trump or the idea of being mayor. 

Looking back thirty years later, this story drips with obvious ironies. No one, and I mean no one, could’ve guessed that on that day in 1992, Trump would become President and later endorse Andrew for mayor (as it turns out for a second time) all these years later.If either of them was on the political fast track back then, it was Andrew. Nor could’ve anyone predicted that Andrew’s political career would end so decisively chasing the very job he was so dismissive of that day.

We’ve had virtually no contact since I stopped working for him in 1993. And while I certainly understand why so many people have negative feelings about Andrew and his entire mayoral campaign, I remain grateful for the opportunity to work with him when I was young. Andrew was good to me and taught me a lot.  While he may have deserved what he got last week, I take no joy in seeing his career end that way.

But most of all this story shines a bright light for me on perhaps life’s most enduring lesson: stay humble.  If you don’t, life has a way of reminding you, sometimes quite painfully.