James "Harold" Massey

James Harold Massey, 89 of Fairfield passed away peacefully at home on May 8, 2026, in Fairfield, Texas. He was born on November 10, 1936, to John Thomas Massey and Letha Mae Brunson Massey in Winkler, Texas. He was a member of First Baptist Church in Fairfield, Texas. He is preceded in death by his father John Massey, mother, Letha Massey Davis, stepfather Coleman Davis, brothers H.L. Massey, R.E. Massey and Johnny B Massey, sisters Mable Massey Anderson, Mary Massey Robinson and Freddie Massey Finley, and son-in-law Bob Rikard. He is survived by his wife of 49 years, Gynne Thornton Massey of Fairfield, TX, daughter Diane Massey Fryer (Hubie) of Fairfield, TX, Lou Ann Massey Humphries (Karl) of Corsicana, TX, daughter Cynthia Allen Rikard of Fairfield, TX, sons Leslee Allen (Jodi) of Itasca, TX and Paul Allen of Fairfield, TX. Thru their 49 years of marriage and blended families they were blessed with 13 grandchildren – Rachel Carney Rhyne (Chad), Jennifer Morris Felton, Chris Humphries (Sydnee), Brandy Humphries Hurford (Mike), Jeff Fryer (Megan) Ben Rikard, Jon Rikard, Andrew Rikard, Nathan Rikard (Sara), Zackary Rikard, Aaron Allen (Emily), Tyler Allen (Alexis) and Sara Allen Jones (Justin). Their blessings continued with 14 great grandchildren – Baylee, Chloe, Conlee, Tucker, Evan, Brooks, Gemma, Macon, Kegan, Ivy, Gideon, Jude, Sullivan, Edith. Maverick, Evan and 2 great-great grandchildren - Braylen and Alayna. He is survived by stepbrother Larry Davis (Verita); stepsister Jeanette Davis LaFrentz (Ralph); numerous “Favorite” nieces, nephews and extended family members; special friends Cameron Perry (Christina, Christian and Nadiyana); brother in-law Don Thornton (Lorraine) and sister in-law Shirley Calhoun. Harold loved being a rancher and cattleman for approximately 55 years before he retired in 2020. He shared this love of ranching with Grady Foree whom Harold came to think of as another son and brother to his children. Visitation and service will be Tuesday, May 12, 2026 – 1-2pm visitation and 2-3pm service at First Baptist Church of Fairfield. Burial will follow at St. Elmo Cemetery in Winkler, TX. Pallbearers will be Chris Humphries, Ben Rikard, Andrew Rikard, Jon Rikard, Nathan Rikard, Aaron Allen. Honorary Pallbearers will be Grady Foree, Jeff Fryer, Tyler Allen, Zachary Rikard, and Cameron Perry. In lieu of flowers donations can be made to: The Commercial Heifer Program of the Freestone County Fair and Rodeo. For details on how to donate, please contact Diane Massey Fryer (254-715-6173).

James "Harold" Massey

November 10, 1936 - May 8, 2026