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Rita Dorothy “Ri Ri” <I>Cunningham</I> Gray

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Rita Dorothy “Ri Ri” Cunningham Gray

Birth
Boston, Suffolk County, Massachusetts, USA
Death
13 Mar 2021 (aged 80)
Burial
Cremated Add to Map
Memorial ID
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Rita Dorothy Gray

Rita Dorothy Gray was born Dorothy Cunningham on May 12th, 1940. According to family legend, she was re-named Rita (Ri-Ri) by her younger brother Phil when he couldn’t pronounce Dorothy. She was the fifth of seven children born to Richard T. and Esther L. Cunningham.

She is preceded in death by her parents, her brothers Dickie, Joe, Johnny, and Phil and her beloved sister and lifelong best friend, Joan.

Rita was born and grew up in the Dorchester neighborhood of Boston, MA. She left school early for work to help support the family, spent her youth around the city with her brothers in various “clubs” (not gangs), and regularly attended the earliest rock n’ roll concerts with her sister. She married first husband Eddie Gray, her “pen-pal” while he served in the military. The two moved to California, became motorcycle enthusiasts, and had two children together—Bonnie and Glenn. She married a second time, gave birth to son Dennis, and ultimately chose to remain single.

Rita was tough. She relocated back to the Boston area and raised her three kids alone during a time that was hard on single mothers. She returned to school as an adult and earned her Registered Nursing degree. She worked in hospitals, nursing homes, home health, and retired from her last and favorite job as Head Administrative Nurse at Dominguez State Jail in Texas. She loved “telling 2000 men what to do every day” and enjoyed welcoming them to her “gated community.” She was well loved by prisoners and colleagues alike.

Rita was a legendary character. She laughed easily, broke into song frequently, and loved to call and sing “Happy Birthday” to loved ones in her Boston accent. She was a hit for her family lore and humor at every Cunningham reunion, to which she famously wore her “Ask Me About My Dysfunctional Family” T-shirt. She dressed in fun for every holiday and loved silly hats and tiaras. A collector by nature, she adored witches, dancing stuffed animals, tigers, anything in the color orange, and so many other little things.

She deeply loved her pets, and cared for many over the years.

Her travels brought her all over the United States, Mexico, and Ireland.

She settled for a long while outside of San Antonio, TX. with sister Joan and brother-in-law Bob Reilly, near her nephews Skip (wife Sharon) and Scott (wife Brandi). She loved the Texas bluebonnets and springtime wildflowers. She later retired to The Villages, FL. near her brother Bob, sister-in-law Nancy, and niece Lisa Cunningham and family.

She is survived by her brother and dear sister-in-law Robert (Bob) and Nancy Cunningham of The Villages, her children; daughter Bonnie Gray of East Bridgewater, MA., son Glenn and wife Margaret Gray of Oakham, MA., and son Dennis and wife Jennifer Gray of San Antonio, TX., and many grand and great grandchildren. If one were to measure her success by her children alone, she raised them into hard-working, moral, and responsible adults.

She asked that her first grandchildren, Courtney, Erin, and Alexis, call her “Grandmama.” Years later, with her last grandchild, Cullen, she became “Nana.” Erin (husband Noel) Leger gave her great grandchildren Steven Strachan, Thomas Leger, and Olivia Leger. She was thrilled for Courtney’s one-on-the-way (with Jed Trenholm) and bragged about knowing the name and gender, a secret to all else. No matter the name she was called, her love was the same, and she took every kid, grandkid, and great grandkid to Disney World at some time or another.

Rita passed in her sleep, peacefully at home, being taken care of by her children, after a fight with cancer, on March 13, 2021.

Daughter, Sister, Mother, “Mum,” Mother-in law, Sister-in-law, Grandmama, Nana, Aunt, Cousin, Friend; Provider, Protector, Encourager, Entertainer, Historian—Rita D. Gray wore all of these titles and more, like her tiaras, with honor. She will be truly missed.

A Mass in her honor is planned for Tuesday, March 23rd at 8:30 AM at St. Timothy Catholic Church, 1351 Paige Place, The Villages, FL. In lieu of flowers, the family asks that you support your favorite animal charity
Rita Dorothy Gray

Rita Dorothy Gray was born Dorothy Cunningham on May 12th, 1940. According to family legend, she was re-named Rita (Ri-Ri) by her younger brother Phil when he couldn’t pronounce Dorothy. She was the fifth of seven children born to Richard T. and Esther L. Cunningham.

She is preceded in death by her parents, her brothers Dickie, Joe, Johnny, and Phil and her beloved sister and lifelong best friend, Joan.

Rita was born and grew up in the Dorchester neighborhood of Boston, MA. She left school early for work to help support the family, spent her youth around the city with her brothers in various “clubs” (not gangs), and regularly attended the earliest rock n’ roll concerts with her sister. She married first husband Eddie Gray, her “pen-pal” while he served in the military. The two moved to California, became motorcycle enthusiasts, and had two children together—Bonnie and Glenn. She married a second time, gave birth to son Dennis, and ultimately chose to remain single.

Rita was tough. She relocated back to the Boston area and raised her three kids alone during a time that was hard on single mothers. She returned to school as an adult and earned her Registered Nursing degree. She worked in hospitals, nursing homes, home health, and retired from her last and favorite job as Head Administrative Nurse at Dominguez State Jail in Texas. She loved “telling 2000 men what to do every day” and enjoyed welcoming them to her “gated community.” She was well loved by prisoners and colleagues alike.

Rita was a legendary character. She laughed easily, broke into song frequently, and loved to call and sing “Happy Birthday” to loved ones in her Boston accent. She was a hit for her family lore and humor at every Cunningham reunion, to which she famously wore her “Ask Me About My Dysfunctional Family” T-shirt. She dressed in fun for every holiday and loved silly hats and tiaras. A collector by nature, she adored witches, dancing stuffed animals, tigers, anything in the color orange, and so many other little things.

She deeply loved her pets, and cared for many over the years.

Her travels brought her all over the United States, Mexico, and Ireland.

She settled for a long while outside of San Antonio, TX. with sister Joan and brother-in-law Bob Reilly, near her nephews Skip (wife Sharon) and Scott (wife Brandi). She loved the Texas bluebonnets and springtime wildflowers. She later retired to The Villages, FL. near her brother Bob, sister-in-law Nancy, and niece Lisa Cunningham and family.

She is survived by her brother and dear sister-in-law Robert (Bob) and Nancy Cunningham of The Villages, her children; daughter Bonnie Gray of East Bridgewater, MA., son Glenn and wife Margaret Gray of Oakham, MA., and son Dennis and wife Jennifer Gray of San Antonio, TX., and many grand and great grandchildren. If one were to measure her success by her children alone, she raised them into hard-working, moral, and responsible adults.

She asked that her first grandchildren, Courtney, Erin, and Alexis, call her “Grandmama.” Years later, with her last grandchild, Cullen, she became “Nana.” Erin (husband Noel) Leger gave her great grandchildren Steven Strachan, Thomas Leger, and Olivia Leger. She was thrilled for Courtney’s one-on-the-way (with Jed Trenholm) and bragged about knowing the name and gender, a secret to all else. No matter the name she was called, her love was the same, and she took every kid, grandkid, and great grandkid to Disney World at some time or another.

Rita passed in her sleep, peacefully at home, being taken care of by her children, after a fight with cancer, on March 13, 2021.

Daughter, Sister, Mother, “Mum,” Mother-in law, Sister-in-law, Grandmama, Nana, Aunt, Cousin, Friend; Provider, Protector, Encourager, Entertainer, Historian—Rita D. Gray wore all of these titles and more, like her tiaras, with honor. She will be truly missed.

A Mass in her honor is planned for Tuesday, March 23rd at 8:30 AM at St. Timothy Catholic Church, 1351 Paige Place, The Villages, FL. In lieu of flowers, the family asks that you support your favorite animal charity

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