With deepest sorrow we at Henryhand Funeral Home regret to announce the passing of Leonard Montgomery,64, husband Sharon Montgomery, of Greeleyville, SC, who passed away on Tuesday, November 11, 2025.

In Loving Memory of Leonard Montgomery

On Tuesday, November 11, 2025, our beloved husband, father, son, brother, uncle, cousin, and friend entered into his eternal rest.

Leonard Montgomery, affectionately known as Len, was born on May 1, 1961, to Ester M. Montgomery and the late Oliver C. Montgomery in Williamsburg County, South Carolina. Len was known throughout his community for his generous spirit and willingness to lend a helping hand in any situation.

At an early age, Len accepted Jesus Christ as his Lord and Savior while attending Biblical Christian Church in the Snow Hill community of Greeleyville, SC.

A proud member of the C.E. Murray High School Class of 1979, Len carried the spirit of his alma mater with him throughout his life. After graduating, he entered the workforce with dedication and an unmatched work ethic. He began his career at Oxford, later continued his service at Santee Oil, and eventually took to the open road as a truck driver, most recently with McKenzie Trucking. In every role, Len was known for his reliability, kindness, and the quiet pride he took in a job well done.

No matter where life took him, Len remained deeply loyal to his beloved Snow Hill community. He made time for others—offering a helping hand, sharing a laugh, or simply being present when he was needed most. To know him was to know sincerity, humility, and a heart full of love.

Len's life was defined by his dedication to his family, his community, and his love of sports. He never met a stranger, and if you spoke with him long enough, he would find a way to connect your story to the family tree. His love for baseball ran deep; he played well into his late 50s, for different teams throughout Williamsburg County. His passion for the sport was matched only by his devotion to his community. To many, he was a father figure—someone they could depend on without hesitation.

He was preceded in death by: his father, Oliver C. Montgomery; his in-laws, Mr. and Mrs. Warren W. Lee Sr.; his brother-in-law, Bruce Lee Sr.; and his son, Dominique J. Montgomery.

Len's memory will be treasured by: his loving mother, Ester Montgomery of Greeleyville, SC; his devoted wife, Sharon Montgomery of the home; his son, Leonard (Shakeima) Montgomery of Sumter, SC. He is also survived by: two daughters, Samantha (Justin) Segres of Kershaw, SC and Jennifer Sherwood of Myrtle Beach, SC; four brothers, Lee Oliver (Cheryl) Montgomery of Florence, SC, Henry (Maggie) Montgomery of Greenville, SC, Christopher (Tonya) Montgomery of Greeleyville, SC and Charles (Latonya) Montgomery of Greeleyville, SC. In addition, he leaves to cherish his memory: two sisters, Beatrice (Jerome) Harris of Sumter, SC and Gwendolyn Starling of Greeleyville, SC; two brothers-in-law, Warren Lee of Rock Hill, SC and Kelvin (Hattie) Lee of Columbia, SC; four sisters-in-law, Ella Kirt of Atlanta, GA, Cynthia (Rodney) Nelson of Greeleyville, SC, Ruby (Eddie) Pompey of Summerton, SC and Cathy Lee of Kingstree, SC.

He will be deeply missed by: his five granddaughters, Chyna Giles, Akhyah Giles, Kamelia Giles, Eva Segres and Olivia Montgomery; three grandsons, Justin Segres, Carter Montgomery and Caleb Segres; as well as his extended family, a host of aunts, uncles, cousins, friends, classmates, teammates. trucking buddies, and countless others whose lives he touched in meaningful ways.

Len's legacy of kindness, passion, dedication, and his unforgettable smile will forever live on in the hearts of all who knew him. He will be remembered not only for his compassion but for the joy, warmth, and love he brought to those around him.

The family will be receiving friends and family at 2908 Easler Highway, Greeleyville, SC.

All arrangements and professional services have been entrusted to Henryhand Funeral Home of Kingstree, SC. 843-354-2292.