MIDDLETON - James “Jumbo” Simon passed away peacefully on Tuesday April 4, 2023. He was born in Middleton on March 13, 1929, the son of George and Margaret (Gorman) Simon. He married the love of his life, Anna Mae Voss, on April 17, 1951. They were married for over 70 years until her passing in January of 2022.

Jumbo was proud to be a lifelong resident of Middleton and well known throughout the community. At a young age Jumbo helped his parents run George Simon’s Tavern & Bowling Alleys (currently The Village Green bar), he was a mailman for more than 40 years, and after his retirement from the post office he worked more than 20 years at Pleasant View Golf Course.

Jumbo was an accomplished athlete earning 11 varsity letters at Middleton High School. After graduation, he attended UW-Eau Claire and earned a letter in football, however, he always had a special love for baseball. Jumbo started chasing foul balls for the Middleton Home Talent team that his father coached before playing for Middleton Home Talent from 1947-1963. During this time Jumbo was a member of three league championship teams (1952, 1956, and 1957), multiple all-star teams, and was also named league MVP. Various quotes from the Wisconsin State Journal and Capital Times describe Jumbo as “…one of the finest all-around amateur baseball performers in these parts…” and “….a righthanded pitcher with a fighting heart….”

Jumbo enjoyed family vacations up north with his children and could even be seen waterskiing at 70 years old. He was a player, coach, and proud fan of his grandchildren and their many achievements. He could be found at any one of their activities, with Anna Mae next to him, giving her the play by play as her eyesight deteriorated.

Jumbo will be missed by so many and remembered in many different ways. Whether it was a “Top of the morning” to the people on his mail route, the friends he made up north, family gatherings with nieces and nephews, or playing euchre with his card playing buddies, he impacted so many.

A special thank you to the staff at Agrace Hospice Care for your unmatched empathy and compassion, and all of those at Cardinal View who welcomed Jumbo into their community.

Jumbo is survived by his sister, Eileen Tesch; children, William (Janet) Simon, Patrick (Tracie) Simon, Jill (Dave) D’Orazio, Jamie (Jeff) Hanson and Jenny (Robbie) Fackender; 14 grandchildren; 15 great-grandchildren, and many nieces and nephews. He was preceded in death by his parents; and his brother, William “Sonny” Simon.

A Mass of Christian Burial will be held at ST. BERNARD CATHOLIC CHURCH, 7450 University Ave., Middleton, on Friday, April 14, 2023, with Father Brian Wilk presiding. Visitation will be held from 10 a.m. until 12 noon with Mass starting at 12 noon. Burial will follow at St. Bernard Catholic Cemetery on Branch Street. Friends and family whom wish to view the Mass may do so via LIVE STREAM found on Jumbo’s obituary page at www.gundersonfh.com.

Memorials may be gifted in Jumbo’s name to Agrace HospiceCare and Middleton VFW William “Sonny” Simon Post 8216. Online condolences may be made at www.gundersonfh.com.

Gunderson West

Funeral & Cremation Care

7435 University Ave.

(608) 831-6761

James M. Simon

March 13, 1929 - April 04, 2023

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