Cover photo for Roland Ray Crandall Sr.'s Obituary
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1943 Roland Ray Crandall Sr. "Rollie" 2023

Roland Ray Crandall Sr.

October 31, 1943 — April 19, 2023

Pewaukee

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Roland Ray Crandall Sr. “Rollie” of Pewaukee passed away on Wednesday, April 19, 2023 at the age of 79. He was born in Independence, Iowa on October 31, 1943, the son of Ivan and Mildred (Meyer) Crandall. 

He was a 1962 graduate of Independence Senior High School. Rollie proudly served his country in the United States Navy in the Submarine Service from 1963 until 1972. He qualified in 1965 aboard the USS Nathan Hale. He served aboard the USS Nathan Hale twice, USS Grampus and a destroyer, the DD Keppler, as a sonar/radar technician.  Rollie was the sailor on the “hot bunk, having served on both blue and gold crews, making many trips around the world under water. 

He will be sadly missed by his devoted wife of 17 years, Mary Ellen Crandall (Cummings); father of Melanie (Eric Petig) Crandall, Ray (Angie) Crandall, Christopher Crandall and Duane Crandall;  his step daughter Anita (Joe) Bromley, his grandchildren, Trace, Hailey, Mackenzie, Connor and Brandon; great-grandchildren, CJ and Caleb; great-great-grandchildren Wesley, Lane. Rollie was excited to learn of baby boy Luna who will be arriving soon; brother Dean (Denise) Crandall; sisters, Diane Crandall and Carma (Bryan) Gasper; nieces, nephews, other relatives and friends. He was preceded in death by his parents, brother Don and granddaughter Alexis. 

A celebration of Rollie’s extraordinary life will be held on Saturday, April 29, 2023 from 1 pm until 5 pm at the VFW Memorial Post 9537, 202 Clark Street, Pewaukee WI. Military honors will be conducted at 2:30 pm by The American Legion Honor Guard from Post 71 in Pewaukee.

Rollie was a very proud veteran and active member of several veteran organizations that included:

Past Commander of The American Legion at Post 71 in Pewaukee.  Formerly with Beaver Dam Post. Served in Waukesha County Council as a Vice Commander, and also served with First District and Dept of WI as Board Member for Camp American Legion.

Member of VFW Memorial Post 9537 and served as an Officer.

Member of USSVI (United States Submarine Service, Inc) at the Great Lakes Base.

Rollie was able to be on the VETS ROLL trip in 2015 and last year on the Stars and Stripes Honor Flight.

Rollie and Mary-Ellen were also active with the Patriot Guard Riders of SE Wisconsin.

What most will remember Rollie for is SANTA.  Mr. & Mrs. Claus traveled thousands of miles together over the past 17 years to bring smiles to the children and adults they visited in veteran facilities statewide, legion functions, our VFW, nursing homes, children homes, hospice care, and anywhere requested.  All as community service on their own time.

The family wishes to thank the awesome staff at Waukesha Memorial Hospital for their extraordinary care, compassion and comfort over the past 17 weeks. To his care team of many specialists, we are grateful for the extended time we were able to have with Rollie.  His big old heart certainly gave it his all.

To our beautiful family, friends, neighbors and our legion and VFW families who visited, spent time with Rollie, called, brought endless supplies of peanut butter cups, butter pecan ice cream and iced tea, and just made Rollie laugh in tough times, thank you.  He cherished your friendships.

Private interment will be at Southern Wisconsin Veterans Memorial Cemetery.

In lieu of flowers, memorials are appreciated to the family. 

Faith, courage, service true, Over Honor, Over all.  Fair winds and following seas shipmate. We have the watch. Bless him. Mahalo for your service, shipmate!

To order memorial trees or send flowers to the family in memory of Roland Ray Crandall Sr., please visit our flower store.

Service Schedule

Past Services

Celebration of Life

Saturday, April 29, 2023

1:00 - 5:00 pm (Central time)

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Military Honors

Saturday, April 29, 2023

Starts at 2:30 pm (Central time)

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