Denny O'Brien checks the cake during his farewell party as he prepares to move to the Oak Park Arms.

The close-knit 700 block of Clarence Avenue gave a heartfelt sendoff to one of their own. Denny O’Brien, who has lived at 716 Clarence — much of that time with his late wife, Fran — for 64 years, is moving a few blocks north and west to the Oak Park Arms. 

O’Brien has been much more than a neighbor. He contributed to the culture of community that makes this block special. He pioneered their block party and served many years as the leader of the kids’ parade. More than that, he and his wife were the gentle souls who kept close ties with longtime neighbors and welcomed newcomers to the block.

The World War II veteran is 95 now but his mind remains sharp and his memories vivid. He reminisced about his wartime experiences at the farewell bash his neighbors threw for him on June 7. The event was organized by his immediate neighbors, Robin Ziegler and Helen Ferraro. Ziegler mentioned that living next door gave her the privilege of having a “backyard relationship” with the O’Briens.

She helped provide the coffee and Irish-themed cake that was enjoyed by more than 40 neighbors and family members who gathered in the honoree’s front yard. O’Brien isn’t the only longtime resident on the block. Richard Katz and John Cline have been there 32 years. Ben Gibbons has called Clarence home for 48 years, Stewart Edwards for 40 years, and former neighbor Kay Costello lived there over 50 years at 731 Clarence. Ann and Stephen Devitt are in their 51st year.

This kind of longevity may be unusual, but it’s an indication that the block’s vibrant spirit makes everyone want to stay. Not only do they have a summer block party, they have a pumpkin-carving party in the fall, and even a progressive dinner to celebrate Groundhog Day. These events are commemorated in three albums packed with photos that circulated at the party. 

Finally, the guest of honor rose to make a brief speech. 

“Thank you, I appreciate this gathering,” O’Brien began, “I’m getting a little older and don’t always recognize faces. But I’m hoping you can keep up the traditions of this block in future years.” With that, he launched into an Irish song, “It’s the Same Old Shillelagh,” about an Irish-American lad who inherits his father’s walking stick.

O’Brien inherited his kind spirit and silver tongue from his Irish parents. He was born and raised in Englewood back when it was one of the choice neighborhoods of Chicago. “It had more churches and banks than any neighborhood,” Denny recalled. Irish Christian Brothers taught him at Leo High School, where he took a one-month course in military training.

He went on to study aviation at De Paul University and attend night classes at Loyola. He did his flight training at what is now Lewis University. After he earned his civilian pilot’s license, he volunteered for the Navy. When war came, O’Brien signed up for the officer training program at Northwestern University and received his commission after three months. The newly-minted “90-day wonder” became a primary flight instructor.

He trained pilots at Glenview Naval Air Station, working a grueling schedule. O’Brien would fly with a student for an hour, get a half-hour break and go back up. He trained land-based pilots, while other instructors worked with carrier-based pilots. These trainees practiced take-offs and landings on the “Wolverine” and “Sable” which operated on Lake Michigan. After they made eight successful attempts, they were sent to the fleet. Many had mishaps, which resulted in hundreds of planes sitting at the lake bottom.

O’Brien occasionally served as co-pilot for officers landing on the carriers, but most of the time he was teaching pilots to land on 15 practice fields scattered across Chicago’s suburbs. His favorite was at Mundelein Seminary, where his younger brother, John, was studying to become a priest. He would buzz the baseball field in a simulated emergency landing. O’Brien stayed an instructor for the remainder of the war. He was “separated from active duty” but remained in the Naval Reserve during the Cold War. In fact, he never did get his discharge and can say that he’s been in the reserves for 72 years.

After the war, O’Brien enrolled in Chicago Teachers College. 

“That’s where I met my lovely wife, Fran [whose maiden name was also O’Brien],” he recalled. “We were seated alphabetically and I had another O’Brien next to me. So I married her.” The couple remained together for 67 years until Fran passed away in June 2013. They raised five children. 

The O’Briens got married in 1946. After they obtained their teaching degrees, he became a physical education teacher for Chicago Public Schools. His first assignment was on the West Side. At the time, he and Fran were living with her mother on the South Side. Wanting to be closer to his job, Denny found an apartment in Oak Park, where they lived for eight years.

With his growing family, he needed income during the summer, so he started his own day camp. It was called Westurban Play Club. He had over 100 kids enrolled and would pick them up and drop them off at their homes. He hired qualified teachers and kept the class sizes small. He ran the camp for seven years and made enough money for a down payment on 716 Clarence. He paid $17,000 for the house.

Their next-door neighbor taught with Fran at Longfellow School, where she was a kindergarten instructor. They lived just down the street from Ascension School, where Fran served as president of the school board for two terms. She was also a minister of care, while her husband served 29 years as an usher. Four of their five children attended Ascension School and the couple remained very active in the parish. 

In the meantime, Denny taught at almost a dozen grade schools in Chicago, before landing a job at the House of Corrections, a school for youthful offenders, age 17-21. O’Brien taught them a full academic program, and they had a strong incentive to attend his classes. 

“If they didn’t go to school, they went to work at the coal factory at 35th & Sacramento,” he recalled. 

He spent his final years as principal of Marshall High School before retiring. During his long career, Denny always had energy left over to socialize with his neighbors and find new ways to have fun. In 1971, he read in the local paper about a block party on Kenilworth. Why couldn’t Clarence do the same? 

“I was the first chairman of the block party and ran the games for years,” he recalled, becoming the pied piper on a block that once housed 60 kids.

“I feel blessed by neighbors,” he said, “I feel surrounded by love and support.” 

Addressing his neighbors, he said, “Ninety-five years is a long time. If anyone has a recollection of something you did for me, or against me, I’d like to hear it.” He spoke of his “wonderful family and grandkids,” two of whom were present. On behalf of his family, he thanked the guests for his going-away party. 

O’Brien may be moving from the block but he will never leave.

Join the discussion on social media!