Douglas Ray Boss, 68, of Manitowoc, Wisconsin passed away on Wednesday, December 9th following a long illness. Doug was a deeply spiritual man and was surrounded by his family as he left this world for the next. Doug was born on September 27, 1952, to the late Leonard and Catherine (Laub) Boss of Ladysmith, Wisconsin. He attended Ladysmith High School and graduated in 1970. Doug was an avid and talented athlete, participating in multiple organized sports. He later joined the United States Air Force and served our country during a difficult time in our Nation's history. In her infinite wisdom, Doug's sister Debra knew that he and Jo Martin would hit it off. She was right. Doug met Jo in January of 1975 and they were married on August 9th in Burlington, Wisconsin that same year. Debra's matchmaking and Doug's multiple trips to visit her (all while pulling multiple cars out of the ditch along the way) lead to 45 years of marriage and friendship. Doug and Jo brought three daughters into this world; Tricia, Kelly, and Chiara. Doug has two sons-in-law, Mike and Pat, and two grandchildren, Ethan and Elli, that he loved with his whole heart. Doug had multiple talents and worked in different areas, excelling throughout his career. He was a remarkable automobile salesman and later served his community as an AODA counselor and finished his career as an Elementary School Guidance Counselor with the Green Bay School District. He had a Bachelor of Science from Silver Lake College and a Master of Arts in Counseling from Lakeland College. No matter what Doug did for work, he did with dedication, love and tenacity. His work ethic and dedication to serving others inspired all who knew him. Doug's greatest love was his family. He loved rummy games with his mother Catherine more than just about anything. Doug was a true outdoorsman and jack of all trades. He shared his love of the Green Bay Packers with his family and that tradition continues. Everyone who met Doug was a better person for it. His sense of humor and jovial spirit brightened even the darkest of days. He is survived by his mother Catherine Boss (Appleton, Wisconsin), wife Jo Boss (Manitowoc, Wisconsin), daughters Tricia (Michael) Spaeth (Two Rivers, Wisconsin), Kelly (Patrick) Palmquist (Kingsford, Michigan), Chiara Boss (Green Bay, Wisconsin) and grandchildren Ethan Peregoy and Elisabeth Spaeth. He is also survived by his sister Debra (William) Tuttle, Doreen (Robert) Fadness, and his angel-on-Earth brother Davis Boss, as well as his godchildren, nieces and nephews, family and friends. Doug was preceded in death by his maternal grandparents Anna and Joseph Laub, his paternal grandparents Muriel and Peter Boss, his dear friend, confidant and father Leonard Boss, and many close family and friends. Doug was also preceded in death by his four-legged friend, Bear and several other furry friends along the way. Family and friends may visit at Our Lady of Lourdes Parish Family, 1307 Lourdes Avenue, De Pere, beginning at 11:30 a.m. until 1 p.m. on Friday, December 18, 2020. A Memorial Service will begin at 1:00 p.m. with Dc. Mike Vander Bloomen officiating. Full military honors will follow the service. Due to COVID-19, please respect social distancing and masking protocol. For those unable to attend, we will be live streaming the service, to view the service visit the Ryan Funeral Home Facebook page to watch starting at 1pm. The full service can be found here: https://www.facebook.com/ryan.funeral.home/videos/725922518325741