Richard Alan Kay

March 4, 1956 ~ October 10, 2020 (age 64)


Richard (Rick) Alan Kay, 64, passed away suddenly and peacefully on October 10, 2020 at his home in Bethesda, Maryland.


Rick was a larger-than-life individual whose generosity was only overshadowed by his love for his family. Born to Al Kay and Shirley Kay in Washington D.C. on March 4, 1956, Rick is survived by his wife, Rebecca Kay, and children Lexi, Brandon, Bradley and Amanda, his brother Larry and Larry’s wife Meredith and their children Aaron, Sydney and Matthew.  


A graduate of the Class of 1976 of Kennedy High School in Silver Spring, MD, Rick earned a business degree from the University of Maryland.


A serial entrepreneur, Rick co-founded his first company in 1987, National Operator Service Inc., a Bethesda-based telephone service reseller, which became one of the nation’s largest telephone service resellers. From his experiences at National Operator Service, Rick saw his next opportunity. In 1992, while still running National Operator Service Inc., Rick founded OTG Software, a storage, content and email management software company. Rick turned OTG Software into a leader in online data solutions and one of the region’s first internet success stories, taking the company public in 2000 and later selling the company to Legato Systems in 2002.


Rick would later serve as Chairman at Sentrillion, a Virginia based company providing integrated technology solutions for national security, critical infrastructure, and vital network communications.


An avid and life-long DC sports fan, Rick was a regular fixture at Washington football, Washington Wizards, Washington Capitals, and Washington Mystics games. Rick would eventually join the ownership group at Monumental Sports and Entertainment, which owns the Wizards, Capitals, Mystics and Capital One Arena. In recent years, it was rare to see Rick without his 2018 Washington Capitals and 2019 Washington Mystics championship rings on his hand.


Along with his wife Rebecca, Rick was a staple of the philanthropic community in the region. His true legacy will be his philanthropic endeavors, including being a Board Emeriti of Best Buddies, a former Chair of Fight Night, the regions premier fundraising event for Fight For Children, and a honorary member of the board of directors of Venture Philanthropy Partners.


In lieu of flowers, the family prefers donations to be made in Richard Kay’s name to The Crohn's & Colitis Foundation or Caring Matters.


The Crohn’s & Colitis Foundation

ATTN: Financial Operations

733 Third Avenue, Ste. 510

New York, NY 10017

To Donate -


Caring Matters

518 South Frederick Ave.,

Gaithersburg, MD  20877


To Donate -


Due to COVID 19 restrictions memorial service details will be announced at a later date.


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