James "Jim" Arvin Raymond, 68, of Waterloo, died Thursday, May 11, 2023, at home surrounded by his loving family and friends. He was born September 7, 1954, in Waterloo, the son of Robert and Mary Tragord Raymond. Jim graduated from West High School in 1972 and worked for John Deere from 1972 until his retirement in 2014. Even as a young man, Jim demonstrated thoughtfulness to other people above himself. Yet, by his own admission, he was shy and reserved. That all changed when, totally by accident, Jim discovered performing as a drag queen. Thus, Ruby James Night came into being in 1995, and Jim continued to perform as Ruby until the end of his life. Ruby gave love to others and found a way to help a person find the good inside of themselves and to let them shine and succeed. Performing as Ruby in Waterloo and around the Midwest, Jim brought joy to thousands, winning awards and titles. Whereas Jim was shy and reserved, Ruby was a persona that Jim considered beautiful and loving. Ruby made friends and Jim in turn embraced them as family. Jim was a founding member of Community AIDS Assistance Project, organized and participated in numerous fund raisers and helping those affected live in dignity, was a member of the Imperial Court of Iowa and was Grand Duchess XII and Empress VII and Empress XVIII of the Imperial Court of Iowa. He was also voted Miss Gay Waterloo in 1998 and 2008, and Emcee for the Cedar Valley Pridefest in Waterloo. Jim is survived by his siblings Robert (Sonya Kosnar) Raymond of Gladbrook, Gary (Andres Herrera) Raymond of Charleston, SC, and Susan (Michael) Osborn of Vinton; his niece Jessica (Scott) Good of Garrison, IA; nephews William E. Raymond of Hanahan, SC, Robert (Monica) Raymond of Moore, OK, Scott Sondag of Vinton and Dustin (Michelle) Sondag of Van Horne, IA; and a very large host of other lifelong friends. He was preceded in death by his parents, sister Mary Lou, brother Larry, and his favorite dogs Buster and BJ. Funeral services will be Saturday, May 20, 2023, at 1:00 PM at Locke at Tower Park, 4140 Kimball Avenue, Waterloo. The family will receive friends Friday, May 19, 2023, from 5 until 8 PM at the funeral home. Private burial at Oakwood Cemetery, Floyd, IA will be at a later date. Memorials should be directed to the family.

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