Kevin W. O'Leary of Boston passed away peacefully surrounded by his loving family on August 10, 2021 at the age of 80. The founder of VPNE Parking Solutions, he was the brother of Joseph Leary, former leader os the Bosotn-based Irish Americn Partnershio.

Kevin graduated with a Bachelor of Science from Boston College in 1962 and proudly served his country as a Lieutenant Junior Grade in the U.S. Navy from 1962-1965. 

Kevin was a man of great charm and wit. After a long career in the investment business, he founded VPNE Parking Solutions in 1990; a company he successfully built with his son Kevin J. Leary. Kevin had a heart as wide as the world. A recovering alcoholic, he shared openly about his own personal struggles. He inspired many, believing in them when they didn't believe in themselves. He truly lived the principles of love, kindness and compassion by giving generously of his time and resources to help those less fortunate. 

He was an active member on many boards and supported many others including Boston Health Care for the Homeless, Nativity Prep, Laboure College, Project Place, the Gavin Foundation, The Phoenix, Rodman Ride for Kids, Camp Harborview, and Christmas in the City. 

Kevin's family was the joy of his life. He was the loving husband of Mary Kelleher and devoted father of Nora Leary and her husband Dan Corey of Milton, Kevin J. Leary and his wife Jenna of Scituate, Matthew Leary and his wife Annie of Wakefield, Timothy Leary and his wife Sarah of Milton, Erica Prince and her husband Kevin of Walpole, and Tess Grande and her husband Jonathan of Milton. 

One of his greatest joys was spending time with his 16 amazing grandchildren; Colin, Michael, Erin, Patrick, Kara, Liam, Ruby, Georgia, Cecilia, Zeke, Sam, Nate, Grace, Connor, Declan and Fiona. He was deeply loved and will be greatly missed. Kevin is also survived by his brother Joseph Leary and sisters Patsy Dowling and Betty Horrigan. 

A Mass of Christian Burial will be celebrated in Saint Elizabeth Church, 350 Reedsdale Road, Milton, Monday, August 16 at 11:30 AM. Relatives and friends invited. Visiting Hours at Dolan Funeral Home, 460 Granite Avenue, EAST MILTON SQUARE, Sunday, 3-7 PM. Interment Cedar Grove Cemetery, Dorchester. 

In lieu of flowers, please honor Kevin by donating to the any of the organizations that meant the most to him including: Boston Health Care for the Homeless, Nativity Prep, Laboure College, Project Place, The Gavin Foundation, The Phoenix, Rodman Ride for Kids, Camp Harborview, or Christmas in the City. To send the Leary family a condolence message, please visit www.dolanfuneral.com