Charles Samual Gregory Jr, 73, of Milford passed away on Monday, December 1, 2025 at Iroquois Memorial Hospital in Watseka. He was born on February 11, 1952 in Watseka, the son of Charles Samual and Bonnie (Parish) Gregory Sr. He married Connie Rule in Paxton, IL on May 25, 1970.
Surviving are his wife, Connie Gregory of Milford; four children, Charles Michael (significant other, Bobbie Sue) Gregory of Texas, Christopher Mark Gregory of Milford, Jeremy Lee Gregory of Sheldon, and Jacqueline DeAnn (Tyler) Wilson of Brook, IN; ten grandchildren and six great grandchildren; one brother, Dan (Becky) Gregory of Milford; two sisters, Linda (Steven) Wright of Evansville, IN and Debbie (David) Lauterbach of Fayetteville, NC; and many nieces and nephews.
He was preceded in passing by his parents and one sister, Sherri Gregory Bray.
Mr. Gregory served in the United States Navy and was a truck driver for over forty years. He enjoyed working on cars with his sons, mushroom hunting, and spending time at home with his family and his dogs, Simba and Charlie.
Cremation rites are being handled by Baier Funeral Home in Watseka.
A private graveside service will be at a later date at Maple Grove Cemetery in Milford.
Memorials may be made to the family’s wishes.
Please share a memory of Sam at baierfuneralhome.com.
