Sean O'Regan

23-Feb-1969 - 10-Mar-2022

Obituary Overview

Sean O'Regan

It is with broken hearts that we announce the passing of Sean O’Regan.

Sean died suddenly on March 10, 2022, in Dartmouth, Nova Scotia following a heart attack. He was 53.

He will be profoundly missed by his wife Lisa (Gillis); children Danny, Maggie, and Aidan; mother, Mary (Furey); brother, Patrick (Cathy); sister, Kathleen (Adrian); uncle, Stephen (Suzanne); aunt, Dr. Mary K W. O’Regan, aunt, Grace Marie (John), aunt, Bridget; in-laws, Jim and Eleanor Gillis, Sean (Lisa) Gillis, Michael (Meaghan) Gillis; nieces and nephews, Grace, Ruth, Charlie, Mary-Jacqueline, Liam, Marlo, Michael, Haleigh, Jackson, and Mya; as well as many cousins and countless friends and lives he touched.

Sean was predeceased by his father, Paul, and his infant brother, Daniel.

Born February 23, 1969 and a proud life-long resident of Dartmouth, Sean grew up in the automotive industry. His family’s involvement in the car business dates to 1915 in Parrsboro, Nova Scotia where Sean’s grandfather S.E. O’Regan operated several automobile franchises through to the mid-1950s. Sean’s father, Paul O’Regan, started in the business in 1974 when he opened a small used car lot and gas station. Paul, later joined by brother Stephen, would grow their business into one of the largest automotive groups in Canada.

Sean’s love for cars started early. As a kid he’d pump gas and wash cars at his father’s shop after school and on weekends. He continued working in the family business part-time while completing his Bachelor of Arts and Bachelor of Business Administration degrees at St. Francis Xavier University. Upon graduation in 1992, Sean joined the sales team at O’Regan’s and not long after was promoted to Sales Manager at the Chevrolet Oldsmobile Cadillac dealership in Halifax.

In the years that followed, Sean held progressively more senior roles in the company and was named President & CEO for the O’Regan’s Automotive Group in 2008. Sean was awarded the highest honour the automotive industry bestows with the CADA Laureate Award for Business Innovation in 2013. He received the Business Person of the Year Award from the Halifax Chamber of Commerce in 2015, was a Hall of Fame winner of Atlantic Business Magazine’s Top 50 CEOs and was the recipient of the Quantum Shift Fellowship from the Ivey School of Business.

Under Sean’s leadership, O’Regan’s has received numerous industry achievements and awards. His contributions have led to O’Regan’s being recognized with the Consumer Choice Award for New and Pre-Owned Auto Dealerships for 12 years in a row, Canada’s 10 Most Admired Corporate Cultures (Waterstone Capital), the Torch Award for Ethics from the Better Business Bureau of the Maritime Provinces, Business of the Year from the Halifax Chamber of Commerce, Platinum Status as one of Canada’s Best Managed Companies (Deloitte), and being honoured twice as the Outstanding Corporate Philanthropist of the Year by the Association of Fundraising Professionals of Nova Scotia.

Sean had a presence that brought joy to those around him. His calm nature put others at ease and his thoughtfulness meant he was often the ‘go-to’ for close friends seeking advice when having to deal with difficult situations. He had a gentleness that showed in his bright blue eyes when he would ask” how are you doing little buddy?” His interest in others was genuine – and his generosity was limitless. Sean’s compassion was extended not only to family and friends but to the larger community.

He often said that you could not be a success in a failed world, and his sense of duty to others was deeply rooted. Very close to his heart was the important work of Churchill Academy which is committed to meeting the needs of children with learning challenges. As a community champion and member of Churchill’s board for over 16 years, Sean was a tireless advocate for advancing their mission to help students find their wings and help prepare them for success in the next stage of their education and in life.


Sean also contributed his time and expertise to support L’Arche, Children’s Wish, the Heart & Stroke Foundation and many others. Alongside his brother Patrick – who was also his business partner and best friend – Sean led a family business that focused on philanthropy. Transformational gifts have been donated to support numerous organizations and institutions dedicated to helping others and building people’s capacity, notably the Dartmouth General Hospital Foundation, the Halifax Central Library and St. FX.

Helping grow people’s capacity was a passion for Sean. He became a trusted mentor to many young entrepreneurs and people who sought to make a difference through their businesses or community focused not-for-profit organizations

An avid sports fan, Sean was a fixture at local sports facilities. No matter how busy his schedule, Sean was a dedicated cheerleader at all of his children’s hockey, baseball and football games. It is entirely possible that he may indeed have been the world’s biggest Montreal Canadiens fan.

Sean had an intense appreciation for music and the performing arts. This extended from performing in high school and university plays, when he was younger, to supporting local organizations like Symphony Nova Scotia in recent years.

Sean enjoyed camping his entire life, as a camp counsellor and director for the Department of Community Services summer camping program in the 1980s and, in later years, on numerous camping trips with his family and friends.

And Sean could sing. While Stan Rogers is credited with writing Barrett’s Privateers, it has been widely speculated that Sean O’Regan has performed the famous sea shanty more than any other musician past or present – delighting eager audiences on large and small stages, in taverns and kitchens around the world.

Sean adored his family and friends. He loved Lisa with all of his heart and soul and could not have been a more loving and proud parent to Danny, Maggie and Aidan. He had an extraordinary sense of humour and delighted in hosting gatherings at their home on Lake Banook (he’d even invite Bruins fans). He was someone who made others better, just for knowing him. His legacy of kindness, humility, and making the most out of every moment, will live on through the many lives that he touched.

Although Sean’s life was cut tragically short, at 53, the love he shared and the impact he made on so many people was greater than most could achieve in a life twice as long. He will be sorely missed.

A visitation will take place in the Auditorium of Churchill Academy, 5 Crichton Ave in Dartmouth on Wednesday, March 16th from 6pm-9pm. As a result of COVID-19 restrictions a private funeral service will be held at Sean’s home parish of St. Peter’s Roman Catholic Church (Our Lady of Guadalupe) 10 Maple St, Dartmouth on Thursday March 17th at 11am. Those interested in attending the mass virtually may view the livestream at

A Celebration of Life and proper Irish send-off will be scheduled in the near future as COVID-19 restrictions allow.

Memorial donations in Sean’s honour can be made to Churchill Academy by visiting

Funeral Details

  • Visitation

    Churchill Academy

    Event Times:

    16-Mar-2022 6:00 PM - 9:00 PM

  • Funeral Mass

    St. Peter's Catholic Church

    Event Times:

    17-Mar-2022 11:00 AM - 12:00 PM

More Details & Directions

Condolences from family and friends

Posted by Karen Nancarrow | 29-Aug-2022

I just heard about Sean's passing. I'm so sorry to hear of this devastating news. I went to university (St FX) with Sean, and spent many nights listening to his incredible voice, entertaining us all. Not only was he a beautiful singer, his love and generosity was shared with his friends through his incredible talent of music. He was a gentle, wonderful man, and I was so sorry to hear of his passing, way too soon. To his family and close friends - I send my deepest, most heartfelt condolences.

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Posted by John Fast | 02-May-2022

Dear Mary, Lisa, Patrick, Kathleen and families. I was deeply saddened to hear of Sean's passing. Sean embodied so many irreplaceable qualities that endeared him to us. His easy laugh - the twinkle in his eyes - his abundant kindness and generosity - always a stickler for fairness and a hard nosed negotiator. Sean was a true leader and he will be missed, but never forgotten. Deepest sympathies, John Fast

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