John Feehery: Speaking Engagements


A Memorial Day Tribute to Jack Fennelly

Posted on May 27, 2019
“Call me Jack.”

That’s what he told me when I first him.

He was a Judge and he was the father of the girl I was dating.   He would eventually become my father-in-law.

There are a lot of Jacks in my family.

My dad was Jack.  My son is Jack.

My wife’s favorite Uncle is Uncle Jack.

Each Jack has their own distinct personality.

And, it can be said with great certitude, that Jack Fennelly was one of a kind.

He died last week of a failing heart, among other maladies.

But if you are going to die – and we are all gonna die – he went the right way.

Three weeks ago, when my kids and I saw him the last time, he had enough energy and spunk to drive his own brand, new red Cadillac himself during the day, and have a Manhattan as his after-dinner drink.

I like the odd Manhattan, every now and then.  Never thought of it as an after-dinner drink but maybe that is something I should now consider.

Jack Fennelly was always teaching me things.

Like my family, Jack was from the South Side of Chicago.

Like my Grandfather, he was a St. Rita graduate.

Like my Dad, he was a Loyola of Chicago graduate.

Like my brothers (and me), he had a deep and abiding hatred for the Cubs.

Like James Joyce, who remained forever fixated on Ireland after leaving it, Jack Fennelly remained fixated on his beloved Chicago after moving to Florida.

He would tell me endless stories about the Chicago of his youth, about Mickey the Mauler, the neighborhood bully who was the Irish version of Leroy Brown, about his days working as a cop on the streets of Chicago, about the fabled White Sox teams of the 1950s.

I enjoyed talking to Jack about my hometown of Chicago because it captured neatly my own memories of my Dad’s memories.

Like Jack Fennelly, I moved away from Chicago for most of my adulthood, but unlike Jack Fennelly, I never really had the full experience of South Side living, mostly because my family moved out to the suburbs when I was 5.

And as any Chicagoan will tell you, living in the suburbs is not really the same as living in the neighborhoods that make Chicago a unique place to grow up.

It was public service that compelled Jack to move to Florida, where he worked as a JAG lawyer for the Navy.  He was a proud Marine, fought in Viet Nam, become a Chicago cop, went to law school at night, and after moving to Orlando, he would eventually become a Judge.  He was the embodiment of the Irish Catholic American dream, the idea that a guy from a working-class family (his Dad was a fireman) could serve his country, go to school and eventually become a respected, influential and important leader.

Jack was a reader.  He would read countless books, starting early in the morning and ending late at night.  He was an active reader, the kind who would take out a pencil and write notes in the margins.

Every once in a while, he would lend me one of his books, and I would wonder as I read the notes what test he was studying for.  But I guess that’s how he remembered what he was reading.  Actually, come to think of it, not a bad idea, although not recommended if you are reading your book on an iPad.

Jack was a law-and-order kind of Judge, and he would joke about how his business was good when crime was high, like during the drug wars in the 1980s, but lately how business was down because the crime rate had plummeted.

He was an Irish Catholic who took his faith seriously, so seriously that he would send his three kids to a Catholic high school an hour away from their home in Stuart, Florida so they could get a proper education.

Jack was also serious about his interest in military history.  Most of the voluminous books in his library had something to do about war, generals or famous battles.  It was one of his favorite topics of conversation when he wasn’t talking about Micky the Mauler or the Chicago White Sox.

That being said, he was no fan of unwise wars.  He was a student of military history, but he wasn’t stupid about it.  He had grave reservations about the Iraq War, and of course, his instincts were right.

Jack was an intellectual who didn’t much care for intellectuals.  He was a street-conservative who wouldn’t be caught dead at a meeting of movement conservatives.  He was a Chicagoan who wouldn’t travel to Chicago because it was too cold.

He had more than common wisdom.  He had wisdom based on a deep reading of history and real-life experiences in the real world, outside the Ivory Tower.

But he could also be a wise-guy.  He could yuck it up with the best of them, he was a drinker and smoker and he never lost touch with his working-class roots.   He was far too smart to be caught up in all the nonsense that suffuses our ailing culture, but he was aware enough of what was happening.  He wasn’t exactly hip, but he wasn’t secluded from the real world either.

He left us far too early, and he will be missed by all who knew him.

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