Jim Flannery: The O.G. Man-in-Law.

[An ode in solemn remembrance]

In 2016, after dating for a few months, Sarah and I broke up for about a year and a half.

I remember feeling aware that during that era apart, I’d perhaps run into her family members since I spent a lot of time in Bridgeport. I was working there quite a bit, but also socially, I could be found at places around the hood like Maria’s or Bridgeport Coffee.

The only family member I bumped into during our breakup window was her uncle Jim.

I saw him at Subway on 31st Street in his suit, probably after his morning at the courthouse downtown where Jim was a Cook County Circuit Court Judge and Presiding Judge of the Cook County Law Division.

He walked up to the line right behind me. There was no way out. I wouldn’t have expected him to be rude. But I feel like he had every right to just say “hi” and that’s it, or even pretend not to see me. But he was very kind to me, cordial and unassuming. He was intentional about making small talk with me. In a world of awkwardness, people who can maintain warmth tend to stand out. It’s inspiring to me.

I think Jim really had the best jokes. Even when it was the same exact joke that I heard him tell in the past, the way he fashioned the gag with this lighthearted spirit, I’d enjoy it just as much as the very first time I’d heard it. It became more about listening to him share the story than hearing the actual punchline.

A mind as brilliant and as efficient as that, there’s no way he’d have any less of a role in society than a judge.

I really liked seeing him at his cottage in Michigan. Just relaxin’ on the back deck. Not only was he a gracious presence but it was remarkable to see how much he and Carol love their grandchildren.

It has always been extraordinary to me how they would invest so much in revamping their Michigan home life to accommodate their grand kids. A giant treehouse, indoor swings, ziplines, boats, full floor padding in the basement for the boys to wrestle about, industrial grade water slides… you name it.

The final conversation I had with Jim was in Michigan. He asked me about my new role at work, and the new company I had taken the job with. I explained the building that my company was headquartered in at 18th Street & Canalport. He knew the very building.

He knew that it used to house a brewery called Schoenhofen, known for brewing a beer called Edelweiss as well as Green River soda pop. I was taken aback by his knowledge because not only am I obsessed with the idea that I work out of an old brewery, but no one who works with me in the very same office knows about it or has any interest in it whatsoever.

Jim shared with me an anecdote during that conversation, about the owner of a bottled water company that operated in that same building sometime after Schoenhofen was shuttered. He told me he knew the water bottle guy, and that there were two wells inside the building. The guy would pull water directly from the ground in my office building and bottle it up after filtration.

Jim once asked the guy how business was doing. He said the guy told him, “Well Jim, I have good news and bad news. The good news is that I sell a lot of water. The bad news is that I lose a nickel on every single bottle.”

I’m a part of a sacred group of men. The group consists of men who have either married directly into the Zigulich family, or men who have specifically married into the tangential universe of the Zigulich family. It’s a storied group fueled by therapeutic rants and epochal tales of disbelief. We don’t get to meet often as a sect, but we are there for each other through the ups and the downs.

The Men-in-Laws.

The crew’s communication exists mostly via text message group chat in a forum of discretion. A platform of safety.

One thread of texts took place directly after Jim’s passing on October 13th, 2023. It had been so long since we messaged, I remember scrolling up to see what the last correspondence had been. The previous message in the queue was a warm-hearted jovial post about Judge Flannery. Inspired awe that took place well before he passed.

It was then that we christened Jim Flannery the O.G. Man-in-Law. The Don of the Clique.

The Original Gangster.

This piece is my solemn ode in remembrance to Jim’s loving and ingenious spirit. Join the Men-in-Laws as we pour out a dram of single malt Irish whiskey on the one-year anniversary of his passing, October 13th, 2024.

[Special thanks to Sarah for encouraging me to write this and post today in celebration of his life well-spent].

5 thoughts on “Jim Flannery: The O.G. Man-in-Law.

  1. Thank you for your kind and loving words about a man whom we all loved and admired.We just spent a lovely day with his family today remembering his great stories and jokes. We will miss him forever

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  2. Thank you for your sincere words about a special man. Yesterday we spent the day instead of mourning his loss ,we celebrated his life. Like you, we all feel luck to have him and his family in our life.

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