Richard Winston Rollison

Sunrise: December 3, 1969

Sunset: March 11, 2024

Richard Winston Rollison, the only child of the late Carolyn Winegan Franklin and Winston Richard Rollison, Jr. was born in Baltimore, MD on December 3, 1969. Richard was affectionately known as “Rich” to most and the “Lotto guy” to many.

Richard attended Richmond public schools and graduated from John F. Kennedy High School. He furthered his education at Norfolk State University, graduating with a Bachelor’s Degree in computer technology in 1992. Rich enjoyed his time at NSU and made many lifelong friends while in attendance.

Richard was raised in a Christian home. He was baptized as a child and attended Fourth Baptist Church in the Churchill section of Richmond. Richard sang in the youth choir and attended Sunday school regularly with his grandparents Kate and Winston Rollison, Sr.

After starting his career in Richmond, VA, Richard returned to the Hampton Roads area where he met and married Anina Nicole Tripp. From that union two daughters were born, Ananda and Alexandra. Richard also gained a third daughter, Ashli.

Richard started his career with GOVA (Games of Virginia) as a technician. It was in that role that he developed his love for the Virginia Lottery. After the dissolution of GOVA Richard joined the Virginia State Lottery as a sales representative. He became affectionately known as the big guy with the booming voice as he loved to talk with his lottery retailers throughout his day. Richard acquired a huge lottery and retail family and went on to serve them up until his illness.

Richard was a creator in his own right. Whether he was building something out of wood or concocting an innovative idea his hands were always busy. Throughout the years he also created music as he had a great appreciation for all genres however, rap and hip-hop were his favorites. You could catch him at any given time creating a beat and his own lyrics.

Richard was a big teddy bear. He was jovial and verbose with a unique sense of humor to say the least.

Richard leaves behind his ex-wife and friend Anina; his daughters Ashli, Ananda, and Alexandra; his grandchildren Payton and Preston; mother-in-love Georgia Tripp; godson Brandon Scott; stepfather James Franklin and a host of beloved friends and co-workers.

Viewing Monday, March 18, 2024 2:00pm - 6:00pm Metropolitan Funeral Service 120 W. Berkley Avenue Norfolk, VA 23523 Service COME IN PERSON OR WATCH SERVICE LIVE ONLINE Tuesday, March 19, 2024 11:00am Metropolitan Funeral Service Berkley Chapel Interment Greenlawn Memorial Gardens 3920 Airline Blvd. Chesapeake, VA 23321

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  1. reply
    Poo Poo says

    Rich I Love You Man I really miss you. I know you’re in the arms of the Lord rest peacefully.

  2. reply
    Sandra Isley 7-11#10911 says

    Please accept my condolences on your loss. Rich was a great guy. Funny, big, loud voice and a smile that would make my day. He will be missed by all in my store.

  3. reply
    Christine Keller @ Va Lottery says

    I’ve worked with Rich for the past 18 years…He was larger than life and had a heart of gold. I will miss my friend…even though it has been a while since I’ve seen or talked to him he has always been in my prayers and in my heart. I will always cherish the memory of running into him at the warehouse and getting my last BIG RICH hug. RIP my sweet friend, till we meet again!

  4. reply
    LISA SMITH says

    We will always remember Richard Fondly.. He was always smiling about his girls… He was proud of them. He as always so kind and respectful.. Just a sweet man. Our thoughts and condolences to Nikki, Ashli, Ananda, Allie, and the Grandbabies.

    Love Gladys Smith & Lisa Smith Taylor

  5. reply
    Marlon (Mario) says

    I love you my brother! I am going to miss you. RIP.

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