Presley Wayne Cheshire

July 24, 1933 – March 9, 2024

Presley Cheshire (90), of Portland, Oregon, passed away peacefully on March 9th, 2024.  He was born in Tucson, Arizona on July 24th, 1933.  His parents, Presley Lewis Cheshire and Vivian Reagan Cheshire moved to Yakima, Washington when Presley was 9, where he grew up with his brother Jim and sister Barbara.  In Yakima, he attended Yakima High School and developed his love for cars, racing, and the art of sales.

In his years before college, Pres became one of the top salesmen at Cheshire Motors, his Dad’s Pontiac Dealership in Yakima.  He loved to share stories of the amazing deals he would make to get eager car owners into a beautiful Pontiac.  His early days also included racing automobiles and skiing.  He was proud of his skiing accomplishments which included working as a ski instructor at Sun Valley and qualifying for the US Olympic trials.

After he graduated high school, Pres attended Washington State University, where he proudly became a Cougar, joined the Pi Kappa Alpha Fraternity, and ultimately achieved his bachelor’s degree in 1951.

After college, Pres moved back to eastern Washington where he married Mary Mike Kennedy in 1957 and they had two sons, Presley Michael and Charles Christopher.  With a new job, Pres and family relocated to Portland, OR in the late 60’s.  In 1975, Pres remarried to Gail Elisabeth Kennedy, where they raised Gail’s son and his stepson, Cary Michael.

Throughout Portland, Seattle, and the entire Pacific Northwest, Pres embarked on his career as a Yellow Page salesman, executive and trainer, for over 40 years.  While he reached the level of Regional Sales Manager, he also loved working daily with thousands of business owners across the country to make their business dreams come true.  Outside of work, Pres had a love for soccer and is known for establishing multiple junior soccer leagues in the Pacific Northwest, and of course coaching Mike, Chuck, and Cary.  Whether working the sidelines on the soccer field, taking trips to the beach, coordinating family reunions with the Cheshire Clan, monitoring his home weather stations, catching the biggest salmon you’ve ever seen, bird watching with Gail, watching the races, rooting on his grandchildren, or telling amazing stories to multiple generations…Pres was there for family and friends whenever they needed it the most.

Pres is survived by his wife Gail Elisabeth Cheshire, of Portland OR, and by his children, Presley Michael Cheshire (and Sue) of Bellingham WA, Charles Christopher Cheshire (and Debbie) of Vancouver WA, and Cary Michael Cheshire (and Michelle) of San Diego CA; his brother James Lewis Cheshire of Richland WA, and his sister Barbara Louise Hooper of Spokane WA, and many nieces and nephews; his grandchildren, Presley Ian Cheshire (and Melissa) of Bellingham, Anna Liisa Cheshire (and Sam) of Tucson AZ, Christopher Charles Cheshire (and Tricia) of Roseville CA, Bradley Michael Cheshire of Vancouver, Avery May Cheshire of San Diego, and Landon Michael Cheshire of San Diego; and his great grandchildren Cameron Christopher Cheshire and Charlotte Lovette Cheshire of Roseville.  Presley is predeceased by his first wife, Mary Mike Cheshire; and his parents Presley and Vivian Cheshire.

A Celebration of Life will be held for Pres on Sunday, June 23rd, 2024, (1-3pm) at the SMILE Station in Portland, OR (Sellwood neighborhood).  In lieu of flowers, the family offers that you consider a small donation to your favorite charity.   We will always remember Presley’s warm Cheshire Cat grin and amazing stories that touched the hearts and minds of us all.