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ROBERT J. GREGG Obituary pic


Born: Jun 26, 1941

Date of Passing: Nov 10, 2022

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June 26, 1941 – November 10, 2022

Bob was a city boy whose idea of country living was spending every possible moment at his parents, Norman and Ivy's cabin, on Falcon Lake. Growing up in the Wolseley area of Winnipeg, he would be found chumming with his brother Ken, his many friends and doing his best to annoy sister Donna.
It was Gary Rummery and wife-to-be, Lil, that introduced Dad to his future – Elaine Nicholls, who over the next 60+ years would change his life. Eventually she talked him into moving out of the city onto the acreage fondly referred to as Gregg's Grove in Cooks Creek. By now their family had grown to include four kids; Bev, Mo, Debbie and Russ. Over time Gregg's Grove was turned into a country paradise with ski trails, a baseball diamond, pond and animals.
Dad was a big supporter of the community. When we moved to the country in 1973, he quickly became an indispensable part of the Hazelridge Community Club. Before he knew it, he was fundraising for building additions, organizing the fair, doing volunteer roofing jobs, building garages for neighbours, doing income tax for half the countryside, and so much more.
Dad loved his family and besides doting on his girls, spent countless hours with Russ and sons-in-law Allan Doern, Richard Nault and Dani Pokornik. These guys became his best friends, and he loved having them around whether they were building a house with Stan Duplak – aka Father Time - fishing, golfing or just enjoying a beer. He also embraced his daughters-in-law Alexa (deceased) and Corene with open arms.
Dad loved so many people and was loved by so many; the families of Ken and Lynda, Donna and Russ, the Nicholls, Batters, and Grants clan, neighbors, clients and almost everyone he met.
From the beginning Dad said he wanted a baseball team of grandkids, and we did not disappoint. The roster includes Jillian (Jeremie Lambert), Jennifer (Kyle Risto), Jodelle, Melanie (Matt Bedard), Wilem, Liam, Rylan, Ben, Teron, Katie, Calli, with "great" additions to the bullpen being Bram and Isla Risto.
Dad had a very strong work ethic and always taught us to love what you do. He started his career at James Richardson & Sons in the 60's eventually becoming an investment advisor with Richardson Greenshields (ultimately RBC Dominion Securities). Even blizzards didn't stop him from enjoying his daily commute to work.
He had an equally strong play ethic and while never competitive, he entertained many; on the golf course, the curling ice, or at the family cabin of 75 years. Dad's claim to fame was jumping off the dock on one ski until well into the later years of his life. He loved to hike and was affectionately titled "father fartz a lot" on the trails where he'd encourage us to sing to pass the time. Dad loved to sing and was well known for leading sing-a-longs; around the bonfire, at family gatherings, at Dugald Estates, in the car… everywhere.
Mom and Dad were inaugural residents at Dugald Estates where they created yet another network of friends. In fact, his greatest wish is that in lieu of flowers, any donations be made to the proposed assisted living residence - Dugald Place. Dad insists you get a tax receipt, so make cheques payable to RM of Springfield and mail to 1000-800 Jaffray Street, Dugald, R5P 0E9.
Many thanks to all involved in our health care system. Dad's favorite sayings to ponder: "There are no bad days when you're at the lake…He's not heavy, he's my brother… What goes around comes around… "
Celebration of Bob's Life: Saturday, Nov 19, at 11 am Cooks Creek Community Center.
To share condolences and memories, please visit Bob's memorial page at

As published in Winnipeg Free Press on Nov 16, 2022

Condolences & Memories (8 entries)

  • Although I'd only met Bob a few brief times, I've spent a life hearing of this guy named Bob Gregg. Whether it was his lifelong friendship with my uncle Tom Richardson, youth friendship with my sister-in-law Myrna Brown (Schindler) at Falcon Lake, or my mom's (Muriel Kinley (Richardson)) growing up with him and eventual client relationship with him, there he was!! Somehow, he made investments interesting for mom to the point of her loving to talk about the world of personal finance and when dad fell ill back in the late 80's he took over doing their taxes (who else!!). Although my mom is now well immersed in the difficult world of dementia, she was quite saddened to hear of Bob's passing, and when I mentioned it to Myrna (in Ottawa) on the phone recently she too was saddened but had to have a light hearted reminder chuckle of their youthful hanging out at Toniata on Falcon Lake. Our condolences to Bob's family at this difficult time and RIP Bob, it sounds like this 81 yrs has been one heck of a good journey!! - Posted by: Darrell Kinley (Acquaintance ) on: Nov 27, 2022

  • Our deepest sympathies go out to Elaine and family. We were clients and friends of Bob. The world is missing a wonderful human being who made the world a better place and a true gentleman. - Posted by: JoAnne and Ron Kullman (Friend) on: Nov 20, 2022

  • My condolences to Elaine and family - I am so sorry for your loss. I worked with Bob in the Richardson commodity dept. Bob truly made our department feel like family, lots of fun. and some got nicknames, arranging baseball games etc. r.i.p. Bob - Posted by: carol vauclair (co-worker/friend at jr/rg) on: Nov 20, 2022

  • Rose + I married + left Winnipeg 57 years ago + whether we met Bob + Elaine in Winnipeg, Metro Vancouver or Falcon Lake we were always met with open arms. Thank you Elaine. Peace be with you Bob. - Posted by: PETER BEAUBIER (friend) on: Nov 18, 2022

  • The world lost the the guy with the biggest smile, biggest heart and not to mention the biggest brat. As a young girl working for Richardsons I knew the highlight of Bob's day was to tease us girls. One day I was in the Concourse and I see Bob. He yelled hey so I walked up to him ready to say I have a name and he started speaking very loud asking if I was on the same corner and how much I am charging now. We never knew what he was cooking that mind of his. Today I was sharing stories with Carol another of Richardson employees. Being a single mom Bob would make sure she got home fast so she could spend time with her son. One day she was working few minutes late and asked if he could wait. Patient Bob waited 1/2 hour and as they were walking to the elevators she put her hands in her pocket and said hey Bob I forgot I brought my car today. He just said Oh you women are all the same. Bob was a wonderful, patient man and I often thought about him over the years.. I'll bet right now Bob and Jim Clayton are turning the heavens upside down playing their practical jokes on anyone that gets in their way. My condolences to his wife, family and friends. R.I.P Bob when I think of you my face still turns red. - Posted by: RoslynSauewtte (Friend from Richardsons) on: Nov 16, 2022

  • I always apprecaited Bob's easy going jovial demeanor. He was a pleasure to do business with. Deepest sympathy. - Posted by: joe czubaty (client) on: Nov 16, 2022

  • Our family has many great memories with Bob! - Posted by: Margaret Richardson (Friend ) on: Nov 16, 2022

  • Our condolences to Elaine & family for the loss of Bob. He truly was a wonderful person to everyone who knew him... We are saddened to learn of Bob’s passing, as he will surely leave a big hole within his family & be missed by all who knew him ... Bob was a real character & would never miss the opportunity to pull a “fast one” on you, if he knew he could get away with it, & later have a good laugh about it.... Rest in peace my friend. Don & Brenda - Posted by: Don & Brenda Palidwor (Friends) on: Nov 16, 2022

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