Philbert Roland Cummings was born July 6, 1940, Port of Spain to Iona Cummings (deceased) and Danlee Cummings (deceased). He was born and raised in Trinidad & Tobago where he met and married, Annette D. Cummings (deceased) July 1959. He moved to Boston, Massachusetts in 1973, and in 1979 Philbert was able to bring his four children to the United States.

Philbert had a love for playing football, watching western movies, and being a taxi driver. He was most known for having one of the cleanest vehicles you would ever see.

Philbert was the father of six children, Dawn McCloud (deceased) Darlene P. McFarlane, Gail D. Cummings, Philbert Cummings Jr, Erica I. Cummings (deceased) and Jillian J. Cummings.

Preceded in death by his two brothers Ellis Cummings and Everald Cummings.

He was survived by many who loved and cherished him. Grandchildren Shamel Proctor, Reginald McFarlane Jr, Realene McFarlane, Darius P. Price, Takiyah R. Cummings, Chanel J. Cowan-Cummings, Nerissa F. Trotman-Cummings, Marquise R. Cummings, Abygail J. Rudder and Charshara R.K. Harris; Great-grandchildren Shamel Proctor II, Khalessi Proctor, Greyson Proctor, Rylee Proctor, Daijon P. Price, Erica K. Cummings, Ta'Leek M. Hall, Destiny C. Price and Adonis A. Rudder-Cameron. One son-in-law Reginald F. McFarlane; two sisters-in-law Glenda Cummings and Rosalynn Cummings; and a host of extended family and close friends.