Chicago Stories: James ‘Jimbo’ Dooley

Stephen P. Conrad
5 min readMar 7, 2022


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‘An Ode to Jim ‘Jimbo’ Dooley’

Jim ‘Jimbo’ Dooley was honored and remembered today. He was 51 years young.

So, we woke early, got dressed on this sunny March Saturday morning only a few weeks before the St. Patrick’s Day holiday, the Chicago Irish holy day. And we made our way to St Margaret Mary on Chicago’s Northside.

That is the way we learned to do it. We learned to be present in one’s life and pay your respects when that time comes. To be part of a man’s sendoff is to know you were part of their life. No matter how big or small a part, you were part of it.

I felt honored to attend his send off. Together, Bobby McGuire and I attended Jimbo’s memorial. Bobby is proprietor of the famously iconic 62 year old Butch McGuire’s Tavern the final establishment of employ on Jimbos Division Street career. We represented our ourselves and Division Streets part in his life.

Like his father Butch, Bobby’s relationship to family, his friends, commitment to his employees and connection to the larger community is tantamount to who he is. Aside of personal connections, they are two men who have much in common and both larger than life. As with so many, Jimbo was more than just an employee to Bobby.

St Margaret Mary is a heavily Irish American though multi-ethnic Catholic parish. It’s a warm church providing a feeling of safety, like protective arms embracing its flock. An old parish with cracked white plaster walls, simple adornments, priests dressed in unpretentious regalia, and few amenities, it’s a Catholic stronghold in the deep blue-collar neighborhood that is Chicago’s Rogers Park. It has held the neighborhood together through good times and bad.

It was an old school Irish Catholic memorial mass of the finest kind, a traditional Chicago neighborhood send off. As the priest made mention of at the very beginning of mass; “In all my years I’ve never seen the church like this”, I doubt St. Margaret Mary was ever as full as it was this day.

On the sidewalk in front of the church’s worn wooden doors a red Chicago Fire Department Captains vehicle was parked. At the doors a burly man dressed in a kilt stood at attention and greeted the line of hundreds of mourners. The line of friends and loved ones wrapped around the church and up the sidewalk of the neighborhood, all hoping for a spot inside when mass began. It was truly a mass befitting a man who had a great effect on many.

Jimbo was a good man who, loved by his family, loved by many. Jimbo, like me, like you, all the Lords’ children was flawed. He and I were afflicted with many of the same flaws of the everyman. Some minor others, not so minor.

For some, another mans flaws can sometimes be too heavy for them to overcome. But those are the kind of people who are generally too busy judging another to examine their own imperfections. Or maybe their judgement is simply a reflection of themselves. It’s hard to look in the mirror sometimes. Jimbo and I accepted ours and each others.

Maybe you didn’t know Jimbo, maybe you did. He was a regular Chicago guy, a neighborhood guy, a dying breed. He was not famous in the traditional sense, though many famous people knew him, and on this day judging from a standing room only crowd he was known by many and loved by many more.

He was big man. He was gregarious, always with a smile, an Irish twinkle in his eyes. He had a way about him that made you feel at ease. He had an ability to diffuse a situation with a smile and a firm handshake. The guy I knew didn’t need to be famous because he knew who he was. How many can say that?

He and I may not have been the oldest or even dearest of friends, but we were friends and we knew and understood one another. We were of the same age and era. We had different lives filled with similarities.

Our joys were simple, the importance of family and friends huge, our concerns deep, and problems often the same. When we shared, we spoke about real stuff. We understood we were of the same school of thought, the old school.

Passerby, witnessing a crowd this large might be inclined to believe the person being waked was a Chicago politician, individual of notoriety or other well-known figure.

Who else would have a crowd of this size to attend their sendoff? A church filled with firemen and cops, and likely a few robbers, lawyers, construction workers, businessmen and homemakers, the well-heeled and not so much so. Who? A true Chicago neighborhood guy that’s who.

Jimbo was every bit of that and more. If the size of the crowd that shows up to see you off to heaven is indicative of the joy you brought to others and the part you played in their lives then his sendoff said it all.

If not famous, he was well known. Maybe not to those not in his sphere or daily acquaintance but have no doubt his area of expertise was in greeting others with a smile, friendly gesture and occasional fist-to-cuff, all which Jimbo, a Division Street door host was more than proficient at.

He was the front man for some of the most iconic taverns in Chicago and the country. His lives on as a true Chicago story.

It’s not an easy job these door hosts have, many with decades on the street. It’s not easy to offer a smile in the face of adversity and throngs of drunken fools who outnumber you daily.

This is what makes Division Street door hosts different than others. Not unlike a well crafted cocktail, one has to be part politician, part mediator, constantly wear a smile, possess a somewhat notorious reputation and not be afraid of the occasional fist-to-cuff.

You have to know how to offer a firm handshake and kiss the babies. Sounds like many a Chicago politician and true Chicagoans. It’s not a job for the faint of heart. Jimbo was great at it.

So today he was remembered, memorialized, blessed and laid to rest. His family, friends, and many others mourn the loss of a good man.

Many were blessed to have Jimbo in their lives. Division street lost a huge personality. Yet, like many before him, his memory will always be there.

On Chicago’s Division Street you never die or fade away, your memory is never lost. You simply take your post at the door and greet those who have come and gone before us. That’s the Chicago way.

“May the road rise up to meet you. May the roof over your head be always strong. And may you be in heaven half an hour before the devil knows you’re dead.” “As you slide down the banisters of life may the splinters never point the wrong way.”



Stephen P. Conrad

A nomad, a gypsy at heart, writer, actor, artist, anti-sycophant, socially maladjusted and comfortably near complete insanity.