Almost 40 people have gathered together in the backyard of this small house on the Southwest Side, so full there is barely any space to see the grass between the party-goers. Every few minutes, a plane taking off from the neighboring Midway airport passes just overhead, momentarily pausing all conversation as they wait for the noise of the jets to diminish.
Despite this disruption, the cheery and social atmosphere is palpable with children running through the yard, bangers cooking on the grill and plenty of drinks being drunk. There are people wearing Cubs merch, Chicago Police Department shirts and one in a Guinness sweater. Just as the sky starts to dim, not one but two birthday cakes are brought out from the house and everyone, of course, begins to sing.
The cakes land in front of the man of the hour as he takes a sip from his beer. His glass reads “Grandpa - The Man. The Myth. The Legend.” Dennis Dobbyn leans forward and blows out the pair of nine-shaped candles on top of the taller cake to officially mark his 99th birthday.
The evening of June 16, the Dobbyn family gathered at the house of their father, their grandfather or their great-grandfather to celebrate the family patriarch and Irish immigrant to Chicago turning 99 years old.
Only a few of Dobbyn’s eight children, 29 grandchildren and 21 (soon to be 22, his son clarifies) great-grandchildren are absent. While all of his children have moved out of the house, most still live in the Chicagoland area with a majority just south in Oak Lawn, some in Lincoln Park and one grandson living as far away as Indiana.
Dobbyn was born in County Clare in 1927 but grew up in County Cork before joining the Irish army as a young teen.
“I ran away when I was a young kid, ran away from home,” Dobbyn said. “I joined the Irish army on the first of October, 1942, when I was fifteen years old. And I did alright. They kicked me out the first time and because I was underage, and I went back in again and they took me.”
After a few years, he said he moved south to Manchester, England where he worked as a double-decker bus driver for three years.
Just one year before she was crowned Queen of England, while driving his bus out of Albert Square, Dobbyn said a police officer instructed him to pull over to let the then Duchess of Edinburgh's horse-drawn carriage pass. With 40 people on his bus just sitting and waiting, Dobbyn asked the officer if they could all get out and watch.
“So I stopped the bus and I said to him — there are 20 people on the bus — so I said to the copper, ‘Do we have to sit here or can we get out and watch?’” Dobbyn said. “He looked at me and said, ‘You’re Irish?’ I said, ‘Yeah,’ and [he] said, ‘“Long as you behave yourself.’”
Later, Dobbyn said he received a draft notice from the British Army and decided that was the right time to emigrate. He and a few other Irish and English boys, bound to avoid the draft, boarded a ship bound for the Great White North.
John Dobbyn is the fourth oldest of Dennis Dobbyn’s eight children, and is the first born after the Dobbyn’s moved to the South Side of Chicago.
“Now this part I don’t know if it's true or not, but it sounds like there’s some truth to it,” John Dobbyn said. “He got drafted into the English army. He said, ‘eff the English,’ so he jumped on a ship and went to Canada.”
After their ship was briefly waylaid off the northern coast of France, they sailed across the Atlantic and up the St. Lawrence River for eleven days before arriving in Canada.
“We landed in Quebec at seven in the morning and the French customs officers, it took us until seven o’clock at night before they cleared us,” Dennis Dobbyn said. “They were all French at that time, in Quebec, and they weren’t too pleased with all these English-speaking people coming into Quebec.”
From there he settled in Toronto and began working for the Canadian Pacific Railway. Eventually he left Canada for Chicago and once again began driving buses, this time for the CTA before retiring in 1991.
“So [Dennis and his wife Cis] came here in April ‘65,” John Dobbyn said. “So, I believe this is a factual statement, that my father is the longest living person on this block.”
Despite being long-time Southwest Side residents and living just over ten miles from Rate Field, the Dobbyns are staunch Cubs fans. John Dobbyn attributed this to the years his father worked on the North Side where he and his coworkers would watch Cubs games during their lunch breaks.
“Growing up, I thought everybody was either Catholic or a Protestant because of the fighting in Ireland,” John Dobbyn said. “And I thought there was only Irish, Italian and Polish, because that was everything. Everybody in our neighborhood was Polish, pretty much. A couple Irish sprung out and a few Italians, so that’s what I thought the world was.”
Much of the Dobbyn family still maintains strong connections to their Irish roots.
A granddaughter in Minnesota owns an Irish dance studio, and another teaches it in Colorado. Three grandsons played for the Midwest Rugby Union 2025 men’s D2 champions, the South Side Irish. His daughter Eileen Desmond owned an Irish pub in Chicago Ridge for 18 years and now owns the Cork & Bean cafe in Oak Lawn.
John Dobbyn said a neighborhood friend who had to leave the party early reminded his father to apply for the Centenarian Bounty, a gold coin signed by the Irish president and awarded to members of the Irish diaspora who turn 100 years old.
According to his family, one of Dennis Dobbyn’s most common sayings is, ‘You should never eat on an empty stomach.’ At his birthday party, surrounded by three generations of family, he followed through on his own advice.
Writer’s note: The writer thanks the Dobbyn family for their hospitality, their offers of food and drink, and to Aidan and Connor Desmond for the ride to the train station.
