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JASON RICHARD CONWAY Obituary pic

JASON RICHARD CONWAY

Born: Jul 16, 1986

Date of Passing: Oct 24, 2025

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JASON RICHARD CONWAY

Jason Richard Conway, aged 39, of Gunton, Manitoba, passed away on Friday, October 24, 2025.

Jason began his life on July 16, 1986, in Brandon, Manitoba, where his parents, Rick and Cindy, were stationed with the Royal Canadian Mounted Police, along with his sister Kim. In 1992, Rick and Jason moved to Winnipeg, while Cindy and Kim were posted to Teulon to continue their policing careers.

It was in Winnipeg that Jason’s many passions began to take shape - starting at age five with all things Ghostbusters and growing into a deep love of NBA basketball by age ten. He spent countless summer evenings shooting hoops on the driveway until dark, dreaming of becoming the next Michael Jordan. His trademark Air Jordans, basketball shorts, and Chicago Bulls tank top were his uniform of choice, and his Space Jam DVD was played until it nearly wore out.

Fate stepped in when Jason moved to his moms to attend middle school. There, he met Carli - the girl with the infectious smile and laugh - who quickly fell for the new guy with the gift of gab. Jason fit right in with Carli’s family, who welcomed him with open arms. That was the beginning of their 22-year love story, and this summer they celebrated their 15th wedding anniversary.

Jason began university but soon changed direction when he received the call to attend Depot in Regina at just 19 years old. Graduating as a Constable in 2006, he proudly followed in the footsteps of his father Rick, mother Cindy, and Uncle Ed by serving in the RCMP. He spent four years posted in McCreary, Ste. Rose du Lac and Oakbank/Beausejour detachments before moving to the Major Crime Division, where he served for 15 years and earned the rank of Corporal. Jason’s tireless dedication to justice led to numerous convictions and earned him the respect and admiration of his peers and Crown Attorneys alike.

Of all his achievements, none meant more to Jason than being a father to his son, Carson. The two shared an unbreakable bond, spending their time together playing sports, listening to music, and exploring the outdoors camping and fishing. Making memories with Carson and Carli was Jason’s greatest joy.

Jason is survived by the loves of his life - his wife Carli and son Carson; his mother Cindy Morris; his father Rick Conway (Norma); his sister Kim Skinner (Rod) and his nephew Lachlan and niece Lilly; Carli’s parents Randy and Sherry Osbak; brother-in-law Randal Osbak; sister-in-law Meghan Osbak and his nephew Bennett; sister-in-law Mallory Osbak, as well as numerous aunts, uncles, cousins, coworkers, and countless friends. He was predeceased by his grandparents, Reg and Vivian Morris, and Margaret (Mag) Conway.

A memorial service will be held at the Teulon Rockwood Centennial Centre, 14 Main Street, Teulon, Manitoba on Tuesday, November 4, 2025, at 11:00 a.m.

Jason was a big man with an even bigger heart. He laughed loud and often, loved deeply, danced hard, sang with passion, and always saw the good in others. He made every room brighter, every joke funnier, and every moment more memorable. Our lives were richer for having known and loved him.

Though his voice has fallen silent,

His laughter still echoes in our hearts.

Love does not end;

it only changes form.



As published in Winnipeg Free Press on Nov 01, 2025

Condolences & Memories (33 entries)

  • I just read Jason's obituary in the Winnipeg Free Press and I want to offer my deep condolences to Cindy and Rick. Many years have passed since we spent time together, but I remember you so fondly and I am so sorry to hear of Jason's passing. I will hold you in my heart and in my prayers. - Posted by: Marilyn Koss (Friend and work colleague) on: Nov 04, 2025

  • To the Conway family. We are devastated to hear of Jason’s passing. We have known the Conway family for many years Rick, Cindi and Ed and send our deepest sympathies at the loss of this beautiful young man. There is another star in the sky. - Posted by: Bob and Darlene Anderson (Friends) on: Nov 04, 2025

  • Carli, Carson, Osbak and Conway families we are so sorry to hear of Jason's passing. We know he was a wonderful husband, father and cherished young man that serviced us well. Hold the memories close. - Posted by: Rhonda and Tim Cameron (friend to family) on: Nov 04, 2025

  • Our sincere condolences to all the families on this sad loss🙏May you treasure all the great memories made. - Posted by: Valerie & Ted Pauwells (Carli’s great Aunt) on: Nov 03, 2025

  • Sending heartfelt condolences to the family . We remember Jason through his kindness, and great smile and laughter. His love in exploring the outdoors and his family. - Posted by: Daphne & Barb (Friends) on: Nov 03, 2025

  • Carli, Carson & family. We are deeply saddened to hear about Jays passing. He held a special place in our family and in our hearts and always will. His laughter was infectious. He made your day better by just his smile, humour and he always had a hug. He will be deeply missed by all. Our hearts are with you all during this difficult time. Much love to you. - Posted by: Lawrence & Leanne Stutsky (Friend) on: Nov 03, 2025

  • God looked around the garden and he found an empty place. He looked down upon the earth and saw your tired face. He put his arms around you and lifted you to rest. God's garden must be beautiful, He always takes he best. He knew how you were suffering. He knew you were in pain. He knew that you would never get well on earth again. He saw the road was getting rough and the hills were hard to climb. So, He closed your weary eyelids and whispered "Peace be Thine". It broke our hearts to loose you but you didn't go alone, for part of us went with you the day God called you home. - Posted by: BJ (Family Friend) on: Nov 03, 2025

  • My brothers and I grew up with Jason in Winnipeg - we were neighbors. I will always remember the awesome childhood memories we had shooting hoops in the driveway, playing hockey on the street, and riding our bikes to the park. My parents still live in our childhood home next to Rick and Norma; it is always a great time catching up and hearing how our adult lives are going. We are absolutely heartbroken at the loss of our childhood friend. Heartfelt condolences to the family and friends Jason leaves behind, we grieve alongside you. Our hearts and prayers are with you. - Posted by: Jennifer (Hernandez) Lavallee (Friend/Neighbor) on: Nov 03, 2025

  • My biggest memory with Jay is in high school. I always fought with my weight and was having a hard time with it. Jay found me in the bathroom crying and asked what was wrong. He didn't leave till I was ok. Also proceeded to pull his shirt off to show that Infact he wasn't "ripped" either lol. That man pulled me out of a dark moment in my life. You'll be greatly missed Connie!!! - Posted by: Will (Friend) on: Nov 03, 2025

  • We are heartbroken to hear about the loss of your Jason. There are no words that can truly ease the pain of such a tragedy, but please know that our hearts are with you. With deepest sympathy - Posted by: Larry & Georgina Nelson (friend) on: Nov 03, 2025

  • I did not know Jason that well having briefly meeting him a few times with his mother Cindy before he joined the RCMP, and running into each other a few times after. I am so sorry for the family's loss. I had the pleasure of working with Cindy in Teulon, those were great years. JP - Posted by: Jean-Paul Tremblay (friend) on: Nov 02, 2025

  • We are so very sorry for your loss. We remember Jason mostly from when he moved to Teulon and Cindy brought Kim and Jason to Stonewall to visit. He was such a firecracker of a young man and went on to great things. We knew he was in the RCMP and our daughter saw him years later, when he was on his way home to Oak Bank, through Stonewall. I heard more about him and how he was doing when Kim worked with me at Stonewall Collegiate for a bit. Our thoughts and prayers are with all of you at this very difficult time. Sadly we will not be able to attend Jason's Memorial as we are away. Sending prayers for strength, healing and peace. - Posted by: Kim & Del Phillips (Family aquaintances) on: Nov 02, 2025

  • An amazing son, brother, husband, and father. - Posted by: Mike Zazulak (Friend) on: Nov 02, 2025

  • Rick, Cindy, Kim and Jason’s entire family! Passing my condolences to all of you on the passing of Jason. Many years have passed since we last spoke but know my thoughts and prayers are with you as you grieve your loss! May he Rest In Peace. Wayne and Janet O’BRIEN - Posted by: Wayne O’Brien (Friend of the family) on: Nov 02, 2025

  • My heartfelt condolences to Jason's family, his coworkers and his community. Those who serve, and have served, their family, community and nation, are fully aware such service can be a heavy burden. A broken heart, disease, a collision of events, whatever the circumstance, whatever the cause, one's passing will ripple through us all. B.R.Walker (Sgt retired) - Posted by: Bryan R. Walker (Retired Member) on: Nov 02, 2025

  • Rick, Cindy, Kim and Jason’s entire family! Passing my condolences to all of you on the passing of Jason. Many years have passed since we last spoke but know my thoughts and prayers are with you as you grieve your loss! May he Rest In Peace. Wayne and Janet O’BRIEN - Posted by: Wayne O'Brien (Friend of his family) on: Nov 02, 2025

  • Rick, Cindy, Kim and Jason’s entire family! Passing my condolences to all of you on the passing of Jason. Many years have passed since we last spoke but know my thoughts and prayers are with you as you grieve your loss! May he Rest In Peace. Wayne and Janet O’BRIEN - Posted by: Wayne O'Brien (Friend of his family) on: Nov 02, 2025

  • Dear Rick Conway $ family, Just to let you know I’m thinking of you all & was so saddened to hear your loss of Jason. Sending you my sincere condolences 💐 ❤️ Love Christine Affleck & family. - Posted by: Christine Affleck (Friend) on: Nov 02, 2025

  • Our sincere condolences to Carli, Carson and all families. Our thoughts and prayers are with you at this time. - Posted by: Lori Wutke/ Sawyer Lambourne/Kelbey Lambourne (Friendship) on: Nov 02, 2025

  • Our sincere condolences to Carli, Carson and all families. Our thoughts and prayers are with you at this time. - Posted by: Lori Wutke/ Sawyer Lambourne/Kelbey Lambourne (Friendship) on: Nov 02, 2025

  • Our hearts are broken for Jason and his beautiful family. Jason is loved beyond words. He was the most friendly and chatty person you could ever meet. We will cherish the memories of Jason, Carson and Randy’s visits to our home in the fall to enjoy outdoor time at the hunting cabin. I know how deep his pride and love for Carli and Carson was, you could see it and hear it when we talked about them. The world is a better place for having had Jason in it. Deepest sympathy to everyone he touched. He is so loved and will be missed. ❤️ - Posted by: Mel McLaughlin (“Auntie Mel”) on: Nov 02, 2025

  • We are so sorry for your loss. - Posted by: Steve and Louise (Friends) on: Nov 01, 2025

  • I remember Jason full of energy and always happy and ready for a chat. I had the honor of marrying Jason & Carli and saw the deep, rich love between them. I wish all his family peace in the coming days. - Posted by: Karen Martin (Hutchinson) (Family friend) on: Nov 01, 2025

  • To all the CONWAY family. It is with heavy hearts we pass along our deepest condolence on Jason’s passing. Our thoughts and memories are with you all today and always. We have always been considered family and glad we maintain contact through all these many years since we worked together in earlier times. As you know we are with you all, although many miles away, in someway, helping you through those difficult days. - Posted by: Lloyd and Peggy (Close Friends) on: Nov 01, 2025

  • Cindy and Family, I cannot imagine the depth of pain you are feeling. I am so sorry for your loss. Jason was a wonderful person. I remember listening to you two laughing and chatting over the phone during those quiet times on surveillance. Jason will be deeply missed by all who knew him. Take care of each other, now and always. Jen (Marco, Dominic, Danica & Francesca) Persichetti - Posted by: Jen Persichetti (Friend and former coworker of Cindy’s) on: Nov 01, 2025

  • It is with the deepest sympathy and sadness that we offer our condolences. Jason ALWAYS acknowledged and greeted each one of us no matter where we ran into him. His infectious smile and big hug were sincere and heartfelt. He always asked about all 3 of our kids, remembering everyone’s names. We last saw him at Pumpkin Fest and his smile lit up his eyes as he updates us on his son Carson and their activities. It was a true privilege to have know him as a teenager and as a young man and father. He will be sorely missed ❤️‍🩹💙 - Posted by: Joel and Kelly Campbell (Kids went to school together) on: Nov 01, 2025

  • Always greeted with a big smile and a hello whenever I saw you! I got to see you on and off with the boys (Nephew - Jayce) between school/events/baseball. You know the small town vibes of Teulon. One memory I still have today is long ago I believe it may have been Terri, Ty you and I cruising around and we saw that weird light in the sky and we all laughed that it was a UFO. At the time a silly thing but now a memory of a good time with you buddy. The world definitely is a little darker without you in it. Sending condolences to his family and friends - Posted by: Jennifer Hay (Proulx) (Friend) on: Nov 01, 2025

  • Cindy and family, friends and coworkers my deepest condolences to all. Words fail me at this time. May Jason RIP. - Posted by: Janice Morin & family (Acquaintance) on: Nov 01, 2025

  • I'm so sorry to learn of your loss. Thinking of you with heartfelt condolences. Ken - Posted by: Ken Beerman (Friend, co-worker of Cindy & Rick) on: Nov 01, 2025

  • I had the honour of knowing Jason and attending his RCMP graduation. I also met his son a few times and worked alongside his parents for many years. Jason was a fine young man from a wonderful family, and his loss is heartbreaking. My deepest condolences to Rick, Cindy, Norma , Carli, and the entire family — - Posted by: Dennis Hanghofer (Friend) on: Nov 01, 2025

  • Such a tragic loss - my deepest sympathy. - Posted by: Noreeen Stone (friend and former teacher) on: Nov 01, 2025

  • This is just heart breaking. Please accept my sincere condolences Rick(Norma), Cindy, Kim, Family, Friends and Colleagues. I know Rick was always so proud of his kids. Rest In Peace Jason and I pray for comfort to Jason’s loved ones, Friends and Colleagues. - Posted by: Nuno Camara (Acquaintance and friend) on: Nov 01, 2025

  • I am so sorry for your loss. My condolences to the family. - Posted by: Dana Worsnop (Former coworker) on: Nov 01, 2025

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