Vanessa Caldwell

Vanessa Caldwell, affectionately known as "Shortstop," "Pebee," and "Nettie" by her beloved mother Cleo, departed this life on April 3, 2025, leaving behind a legacy of love, laughter, and unforgettable memories. Born and raised in Portsmouth, Virginia, Vanessa was a proud "Manor Girl," deeply rooted in the Cavalier Manor community and always proud to call P-Town her home.
At the age of 18, Vanessa embarked on a journey of independence by attending Job Corps, which led her to spend time living in New York. However, her heart remained in Portsmouth, where she devoted over 40 years of service working in many of the city's local and popular restaurants. Whether serving customers or laughing with co-workers, Vanessa's radiant smile and positive attitude left a lasting impression on everyone she met.
A woman of warmth and heart, Vanessa had the biggest and sweetest spirit-she made all who crossed her path feel seen, loved, and valued. She was an avid sports fan and a loyal supporter of her favorite NFL team, the Dallas Cowboys. She also loved playing cards with family and friends, with Spades being a cherished pastime. Family was everything to Vanessa, and she took great pride in spending time with her nieces and nephews, who loved her dearly and will always remember her joyful energy. Despite having worked in fine restaurants, Vanessa had simple pleasures-one of her favorites being a Whopper from Burger King. Her humility, humor, and deep affection for her community and loved ones will never be forgotten.
Vanessa was preceded in death by her loving parents, Henry L. Caldwell and Cleo E. Blackman, as well as her dear brother, Albert H. Caldwell. She leaves to cherish her memory her siblings: Loretta "Faye" Bazemore (Henry), Phillip B. Caldwell (Jobynia), Fletta O. Caldwell, Terry L. Caldwell, and September Caldwell Nickens. She is also survived by a host of nieces, nephews, cousins, and special friends who were blessed by her life and love.
Vanessa's memory will live on in every heart she touched. May her legacy of joy and compassion continue to shine brightly.
Viewing:
Friday, April 11, 2025
2:00 PM to 6:00 PM
Metropolitan Funeral Service
5605 Portsmouth Boulevard
Portsmouth, VA
Celebration of Life:
COME IN PERSON OR WATCH ONLINE
Saturday, April 12, 2025
11:00 AM
Metropolitan Funeral Service
5605 Portsmouth Boulevard
Portsmouth, VA
Laid to Rest:
Greenlawn Memorial Gardens
3920 Airline Boulevard
Chesapeake, VA