After a brief time apart, Penny Jean O’Rourke Diggs left this world to join her devoted husband, William Winfrey Diggs, Sr. on June 14, 2026. Though our hearts ache, there is comfort in knowing that the two can rest together.

Born September 4, 1961, Penny lived a life marked by strength, kindness, and commitment to her family. Those who knew her understood that she loved her husband with a devotion that shaped her life.

She is survived by her daughter, Sandy Findlay (Kevin); her grandchildren, Judiah Strouse II, Rourke Strouse, and Irelyn Strouse; and her siblings, Jay O’Rourke (Joan) and Bridget Mitchell (Dallas).

She is also survived by her stepchildren, Michelle Breeland, William Winfrey Diggs Jr. (Antonia), and Kimberly Sperling (Todd); grandchildren, Robert Bellamy, Jessica Rafnson (Dylan), Daniel Bellamy (Tristan), Alexander, Maria, and Sophia Diggs, Karen and Daniel Sperling; and great-grandchildren Kairi and Damien Bellamy, Ella, Willow and Kaden Rafnson, Owen and Justice Bellamy, Martin, Jayden, and Rosey Ortiz.

She dedicated her life to serving the community through law enforcement. She attended college as a full-time working mother and earned a bachelor’s degree from St. Leo University. Serving York-Poquoson Sheriff’s Department for 25 years, she was a School Resource Office for Grafton schools and she was the first female Lieutenant of Investigations. She was especially proud of the impact she made protecting women and children.

There will be a private graveside burial on Thursday. In lieu of flowers, memorial contributions may be made to York Poquoson Sheriff Office Community Fund (K9 Unit) PO Box 99, Yorktown, VA 23690.

Arrangements and heartfelt guidance through Claytor Rollins Funeral Home.

Online condolences may be shared at claytorrollins.com.