School chess coach Shawn Martinez saw Tanitoluwa's potential after observing him excel in the game a few weeks after first learning it early last year.
He reached out to Tanitoluwa's family about joining the school's chess program, and learned they were unable to pay costs associated with membership. Makofsky decided to wave Tanitoluwa's fees, which can easily exceed thousands with travel and chess camp admissions.
A student gifted Tanitoluwa a chess clock. Tanitoluwa's mother took him to free regular three-hour practice sessions in Harlem. His dad lets him use a laptop to play chess online.
Seven trophies later, the elementary school boy is one of the top players in the country for his age group.
"He works very hard at his game," Martinez said, estimating Tanitoluwa could achieve master status "in the next year or two." The world's youngest grandmaster qualified at the age of 12.
As Tanitoluwa's story hits national headlines, more people want to help.
Makofsky, who set up a GoFundMe for Tanitoluwa, said the family has received offers for a car, legal services, jobs and even housing.
"My hope is that he'll be in a home tonight," Makofsky said.