Dennis O'Loughlin
March 19, 1940 - May 22, 2025
Obituary
To view a livestream of the Mass of Christian Burial for Dennis O'Loughlin at 11:00 a.m., Friday, June 6, 2025, please visit the following link: Live-stream Mass - Pastorate 17 - Nativity of the Lord - DeForest, WI
Dennis J. O’Loughlin, age 85, passed away peacefully on Thursday, May 22, 2025, at home after a long battle with cancer. Dennis was born in Clinton, MA, to Anthony J. and Mary J. (O’Malley) O’Loughlin on March 19, 1940. After graduating from Clinton High School, Dennis attended Fitchburg State University in Massachusetts before joining the U.S. Air Force in 1959. Dennis was stationed at Truax Air Field in Madison, WI. After serving four years, Dennis joined the WI Air National Guard in which he served for 32 years. Dennis retired as the Assistant to the Adjutant General for the State of Wisconsin and was inducted into the Wisconsin Air National Guard Hall of Fame in 2004.
Dennis was a firm believer in community service and served on the Board of Directors of many nonprofit organizations and service clubs in Wisconsin and Illinois throughout the years to include, among others, the Salvation Army, Rotary Club, Madison Area Builders’ Association, and the Greater Madison Convention and Visitors Bureau. Dennis was also elected to the Dane County Board from 1998 to 2018, serving on many committees, as well as the Dane County Regional Airport Commission for 13 years.
Dennis felt privileged to represent Dane County with the Wisconsin Counties Association (WCA) serving on the Board of Directors from 2002-2018, acting as President from 2008 to 2009. He also served on the National Association of Counties Board of Directors from 2012-2018, the WCA Services, Inc. Board of Directors from 2008-2025, and was a Founding Board member of the Local Government Institute from 2007-2025.
Throughout his career in finance and mortgage lending, Dennis worked at various organizations in WI and IL and ended his career as a partner with Badger Mortgage, LLC.
Dennis was proud of his Irish heritage and had the Irish love of life, strong religious belief, and sparkling sense of humor. He enjoyed meeting new people and loved to travel the countryside on his Harley Davidson motorcycle. He was an avid Boston Red Sox fan and enjoyed golfing, flower gardening, and spending time with family and friends.
Dennis leaves behind his wife of 31 years Sara (Bollig), sons John (Sue) and Jim (Nalini) O’Loughlin, grandsons Bradley (Kyela) and Jacob O’Loughlin, and Johnny and Joseph Kaney; his sister Peggy (Kevin) O’Toole, brother Kevin (Maureen) O’Loughlin; and in-laws Rita (Larry) Zimmerman, Paul Bollig, Claudia Prunuske, Frank (Carol) Bollig, Mary Bollig, Ann West, Virginia (Dennis) Nelson, Tom (Barb) Bollig, Cindy (Chuck) Schwierske, Kris (Tina) Bollig, Kurt (Brenda) Bollig, Keith Bollig, and Doug (Shawn) Bollig, as well as many beloved nieces and nephews. Dennis is preceded in death by his parents Anthony and Mary O’Loughlin, his brother Tony, his daughter Julie Kaney, and his parents-in-law Herbert and Katherine Bollig.
A Mass of Christian Burial will be held at 11:00 A.M. on Friday, June 6, 2025, at St. Olaf’s Catholic Church, 623 Jefferson Street, DeForest, WI. Visitation will be on Thursday, June 5, 2025, from 5:00 P.M. to 7:00 P.M. at Ryan Funeral Home, 6924 Lake Road, DeForest, WI.
In lieu of flowers, donations may be sent to UW Health Carbone Cancer Center, https://give.wiscmedicine.org/give/392780/#!/donation/checkout or Agrace Hospice, https://www.agrace.org/donate/donate-today/.
To view his obituary or leave a memory, please visit: www.ryanfuneralservice.com.
Ryan Funeral Home & Cremation Services
Windsor/DeForest Chapel
6924 Lake Road
608-846-4250
Events
Visitation
Thu Jun 5, 2025 @ 5:00 PM - 7:00 PM CDT
Ryan Funeral Home • 6924 Lake Rd, Deforest, WI 53532
Mass of Christian Burial
Fri Jun 6, 2025 @ 11:00 AM - 12:00 PM CDT
St. Olaf Catholic Church • 623 Jefferson Street, DeForest, WI 53532
Photos
Memories
MM
Marilyn Martin
Family •
My deepest sympathy for Dennis family I remember him as a very friendly, caring guy. I remember his service for the community. Sending prayers for family, friends, and community. Thank Y Dennis for all your service.
DR
Dave Ripp
Friend •
My sympathy goes out to Sara and the whole O'Loughlin family. I served with Dennis his whole time on the County Board. A true pleasure to work with. Friendly, honest, and didn't play games. You knew where he stood on issues and did his best to represent his constituents. His passing is a loss for all of Dane County.
BD
Brian Derr
Friend •
I’m truly sorry to hear about Dennis. He was a kind soul, a patriot, and a great friend to my dad—that’s how I first came to know him, working together through local political business. I’ll always be thankful for his help when I bought my first house, and I genuinely enjoyed running into him at motorcycle events over the years. He was well respected, and I deeply appreciate his service—as he did mine. My thoughts are with his family and friends during this difficult time.
MH
Mark Hazelbaker
Friend •
If we're lucky, we get to meet a few people like Dennis O'Loughlin in our lives -- people who serve others while enjoying the gifts life offers and spreading joy and humor along the way. I knew Dennis from his work with Dane County, but also as a real estate professional. He brought excellence to everything he did. He was a good man. I will miss him.
JL
Jeremy Levin
Friend •
My sincerest condolences to you Sara & the family. I had the pleasure of overlapping with Denny in his second decade of service on the Dane County Board. While we didn't always agree, we definitely held mutual respect for each other and I appreciated his service to his community and country. May your memories together bring solace in this difficult time.
JB
Jim Bricker
Friend •
My sincerest sympathies to you and your family. I will always remember Dennis for his genuine commitment and interest in service to the community, friendliness, and sense of humor. Jim Bricker (former Town of Windsor Administrator)