Jim Kakouros

Jim Kakouros
January 14, 1971 – August 27, 2025
A man has passed—but Jim Kakouros will never be defined by a pair of dates on a gravestone. He was a son, a brother, a cousin, a friend, a mentor, and a force of nature whose presence lit up every room. On August 27, 2025, Jim left this earthly realm for his next great adventure.  He took on the Big C with the same bravado, discipline, and tenacity that highlighted his life and lost after a long fight.
Born on January 14, 1971, Jim was the second son of George and Angela Kakouros and the younger brother of Frank Kakouros. He was a beloved brother-in-law to Roula Kakouros and the cherished “funcle” to Angeliki Kakouros. He had two first cousins Frank and Chris he grew up with that were as close as could be. Though no longer married, he remained close with Melissa Kakouros—the love of his life—who will miss him dearly. Jim was a nephew and cousin to many across Canada, Greece, and the United States, and a true friend to countless others.
Jim graduated from Ajax High School, where he stood out academically and athletically. On the basketball court and rugby pitch, he earned the nickname “Kamikaze” for his relentless, all-or-nothing style of play. Wins came often, along with sprains, bruises, and stories that are still retold.
He went on to study commerce at Queen’s University in Kingston—where, as many would say, he majored equally in partying. After earning his CA designation at Ernst & Young, Jim returned to his entrepreneurial roots, rejoining the family business where he truly thrived.
For nearly four decades, Jim was a greatly respected operator in Ontario’s hospitality scene, working with his closest cousins Chris and Frank, and his brother Frank. Together, they created and operated legendary institutions including Petrina’s Billiards (opened in 1988 in Ajax), Riley’s Pub, The Junction in Oshawa and Peterborough, and, for a time, Petrina’s in Orillia. Jim helped serve great food, great drink and lots of good times to hundreds of thousands who frequented his establishments since 1988. Jim began shaping the industry long before he was old enough to put a liquor license in his name. His guiding philosophy was simple: Keep the customer happy, and they’ll keep you happy.
Jim mentored hundreds of young people over the years—staff members who remember him not just as a boss but, as a life coach and friend they could discuss anything with. He led with integrity, clarity, and heart, always treating his staff as essential partners in the business. There were legendary barbecues, epic Blue Jays outings, and unforgettable Christmas parties—some of which ended in food fights, because with Jim, fun was never far away.
A true sports enthusiast, Jim’s passion started early—as the youngest cousin, he was often the designated tackling dummy. That enthusiasm never faded. He cheered endlessly for his beloved Pittsburgh Steelers. One outing saw him witness a Steeler win over Arizona in the Super Bowl. He watched every major championship and had a memory for names, details, and history. His lifelong passion was with golf. He played courses across Canada, the U.S., and the U.K. There were so many golf trips with so many that always were filled with jokes, camaraderie and too much food and drink. For Jim, the 19th hole was always the highlight—a place for laughter, drinks, good food, and better company.
Jim’s appetite—for food and life—was legendary. There wasn’t a steak dinner he didn’t enjoy (and many 60+ ounce cuts didn’t stand a chance). Only the infamous 128-piece bacon sandwich ever bested him. At age ten in Greece, he famously downed 20 souvlaki sticks—before dinner. Turtles, wine gums and ice cream always were nearby.
He loved pushing limits. He raced a NASCAR vehicle around a track at high speed. He jumped out of planes. He bungee-jumped. And he once braved a rural Virginia church buffet where nothing that was presented was identifiable. Las Vegas was always an adventure—golf and drinks with the boys, or Celine, Cirque, and fine dining depending on the company.
Remarkably, Jim was even mentioned in Rolling Stone Magazine—a fitting tribute to someone who lived like a rock star in all the best ways. His humour, loyalty, and unmistakable presence left an impression on everyone he met.
Jim helped raise hundreds of thousands of dollars through the years for various charities because it was what a good citizen should do. He loathed government waste and politicians who were not brave enough to make the right decisions. He relished a great debate with anyone on anything he knew about.
Jim Kakouros was one of a kind. His laughter lingers, his stories live on, and his memory will be cherished forever by all who had the good fortune to know him.
In memory of Jim, and in lieu of flowers, please consider making a donation to the Peterborough Regional Health Centre Foundation (PRHC Foundation) – Cancer Care Clinic.
Friends will be received at the HIGHLAND PARK FUNERAL CENTRE 2510 Bensfort Rd., Peterborough on Wednesday, September 3, 2025 from 5:00 PM to 8:00 PM., and on Thursday,
September 4, 2025 from 9:00 AM to 10:30 AM, at Evangelismos Tis Theotokou Saints Nectarios and Gerasimos Greek Orthodox Church, 399 Farewell Street, Oshawa, ON L1H 0M1.  Funeral Service will be held on Thursday, September 4, 2025 at 11:00 AM Evangelismos Tis Theotokou Saints Nectarios and Gerasimos Greek Orthodox Church, 399 Farewell Street, Oshawa, ON L1H 0M1. 
In memory of Jim, and in lieu of flowers, please consider making a donation to the Peterborough Regional Health Centre Foundation (PRHC Foundation) – Cancer Care Clinic. Online  condolences may be made at www.highlandparkfuneralcentre.com