Sitting in an office building on the Lower East Side of Manhattan this fall, Mr. Cummings recalled that his mother had led an unrooted life. After his older siblings had left home, he and his mother spent several years traveling, beginning when he was 7.
“She wanted to get me out of the city,” Mr. Cummings said, adding that Ms. Kisselovich had expanded his worldview beyond the housing projects where he had grown up on the Lower East Side and in New Jersey. Over three years, they lived in Puerto Rico, the Dominican Republic and Grenada, as well as Anguilla and the French West Indies. Ms. Kisselovich, who had been employed in banking, began working in education, and Mr. Cummings attended schools with self-directed curriculum.
“That experience definitely changed me,” he said. “It opened my mind and let me see things differently.”
They returned to the United States, living in New York and New Jersey before settling in Florida when Mr. Cummings was about 12. There, he graduated from high school and his mother pursued her nursing degree.
Instead of heading to college, Mr. Cummings took a job refinishing pieces at a furniture company in Queens. After four years, his job was terminated amid cuts in 2009, and he did not have another one for the next eight years.
A year after Mr. Cummings was laid off, his son, Jadice Cummings, was born. Around the same time, his father, Illinois Cummings, a Vietnam veteran and retired corrections officer, had a pair of debilitating heart attacks. Then in his late 20s, Mr. Cummings moved in with his father in the East Village to care for him. His dream of going to college seemed like a remote possibility.
In 2014, Jadice began a Head Start program in the East Village. The Educational Alliance, a beneficiary agency of UJA-Federation of New York, one of the eight organizations supported by The New York Times Neediest Cases Fund, runs the program. And Mr. Cummings “jumped on the opportunity” to participate in the alliance’s College Access and Success Program, which helps parents boost their children academically while providing support for them to pursue higher education themselves.
In September 2015, Mr. Cummings enrolled full time at LaGuardia Community College, where he is working toward the goal of going into communications or helping others pursue higher education. The Educational Alliance helped him navigate financial aid applications, and the New York State Tuition Assistance Program and a federal Pell Grant have eased the tuition burden. But when he recently reduced his schedule to part time to handle family matters, he lost some assistance, accruing $800 in student loans.
When his mother died in April, he was not financially prepared. Until recently, Mr. Cummings, who still lives with and cares for his father, relied on his father’s military retirement benefit of about $1,200 a month to cover their $950 rent. So he collected funds from family and friends to make the journey to Florida. He also reached out to the Educational Alliance, which provided him with $2,650 from the Neediest Cases Fund to cover the cost of a viewing and cremation.
As the months passed, Mr. Cummings kept up with his schoolwork while going back and forth to Florida to care for his uncle, until his death in June. Despite family obligations, Mr. Cummings passed algebra with a B-plus.
He is currently dealing with the estates of his family members, ping-ponging between New York and Florida. His mother did not have life insurance or a will, and left substantial debt; his uncle also died without a will or insurance.
“I’m beat,” he said from a Florida airport. “The fight to save what’s left will lead me down this road again.”
Handling family responsibilities has delayed Mr. Cummings’s graduation. He took November off and now plans to graduate by June. Looking toward graduation, he balances part-time classes with a full-time job he started in August, as a truck driver for a chemical company. He makes about $100 a day.
Mr. Cummings and his son continue receiving services through the Educational Alliance. Jadice, now 7, is enrolled in a Boys & Girls Club after-school program, and Mr. Cummings says he owes an “emotional debt” to the organization. He remains focused on fulfilling his mother’s wish that he graduate from college, which will put him on a better track to provide a safety net for his family.
“It’s been a roller-coaster ride,” he said. “But it’s a process.”
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