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In Memory of Robb Simpson

Celebration of Life

4:00 pm - 8:00 pm
Friday May 13, 2022
St. Croix Training Center
422 County Rd F
Hudson WI, 54016

A life well lived 


Robb ”Big Dog” Simpson of Lakeland, Minnesota, died surrounded by his family on March 18 after a courageous 9-month battle with multiple illnesses. He was 72. 


Robb is preceded in death by his parents, Jack Simpson and Jackie (Weber) Simpson and brother Rich Simpson. He is survived by his wife, Gail Simpson, his children Casey (Lindsay) and Cory (Emily), and his three grandchildren Crosby, Cullen and Coyer. 


Robb spent his earliest days in Roseville, Minnesota, with his dad Jack, mom Jackie, and his younger brother Rich. As a child, he had an avid interest in golf, animals and cars. 


His love for nice cars began at a very early age. Robb first worked at Bob Olson Motors and then later with his dad buying and selling cars in St. Paul. 


Robb and Gail met in May of 1987 and married that summer in August, giving Robb his first chance of parenthood with Casey. Their family was complete with the arrival of Cory in the fall of 1988. 


As a family of four, they traveled all over the Midwest for horse shows each summer. As a family they enjoyed going to movies, hockey games, and spending time at the family cabin in Spooner, Wisconsin. 


Later in life, he transitioned to owning a appraisal company, where he appraised hundreds of homes before retiring in 2008. 


During retirement, Robb managed many of the day-to-day logistics of St. Croix Training Center alongside his wife Gail. Between equipment, motorhome and truck maintenance, errands for supplies and the occasional coffee and donut drop off at the barn, he provided unwavering, constant support. Robb was affectionately known as the “Horse Show Dad” to clients and a cheerleader at every event. 


The cabin in Spooner was Robb’s “happy place” where he was always the captain of the pontoon. Weekends were spent playing cards, relaxing on the deck overlooking Big McKenzie Lake, and sunset cruises with his favorite to-go drink: a Brandy Alexander. 


Spending quality time with his family was Robb’s favorite pastime. He loved meeting for dinner to celebrate birthdays and catch up with his adult children. He loved nothing more than when his grandkids visited and would sit on his lap. No matter what was on TV, he would change the channel anytime one of the little boys wanted to watch cartoons. He often told Gail, “We did good,” as he reflected on the life they built together. 


Robb had many frequent phrases he would say, some not suitable for this audience. There are a few we will never forget as we move forward in this life: 

  1. Drive fast and take chances. 
  2. Always be smarter than the horse. 
  3. Give, give in, forgive, and never keep score. 


An open house celebration of Robb’s wonderful life will be held on May 13, 2022 from 4pm – 8pm at St. Croix Training Center (422 County Rd F, Hudson, WI 54016). 

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Robb's Tribute Wall

Tributes (2):

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    • Robb touched the lives of many people. He was always at the horse shows willing to lend a hand and encouraging everyone! I really enjoyed spending time with him at the shows and the barn. He will be missed by everyone! He was a wonderful person! Our thoughts and prayers will be with your family!

    • I liked Robb the minute I met him, but then, most people did. I don’t think I’ve ever known a bigger hearted or more tender hearted man. Maybe it’s ironic that at the end such a big heart would be a problem. Robb did love his family and he truly was the best cheerleader for all of the barn clients but especially for Gail. I don’t think I’ve ever known anyone as supportive and caring as he was. Always a smile, always a laugh and always a friend. God bless Robb. Gail, it’s a tough road ahead but I know you are up to it. God blessed you with 2 families… obviously your children and grandchildren, but also your horse show family that you’ve shared your life with for 50 years now. God be with you.