Diddy’s fall from grace: Sean Combs seen in high school yearbook pics amid sex trafficking charges

Amid what has been the most challenging year in the life of music mogul Sean “Diddy” Combs, Ny Breaking.com looks back on simpler times for the rapper, when he was still a student at a Catholic high school in the Bronx.

Combs, 55, was seen in a series of images (provided by Seth Poppel of Yearbook Library) from his time at Mount St. Michael Academy in Mount Vernon, New York, about 25 miles north of his current residence at the Metropolitan Detention. Downtown, Brooklyn.

The Can’t Nobody Hold Me Down artist remains in federal custody more than three months after his September 16 arrest in Manhattan on sex trafficking and racketeering charges, with prosecutors alleging he used blackmail and violence in his efforts to kidnap victims to silence.

One of the claims is that he persuaded women to participate against their will in sexual group exhibitions called ‘Freak Offs’. Combs, who is also charged with transportation to engage in prostitution, has made three unsuccessful attempts to get bail amid concerns from the court that he might try to flee or tamper with his case.

Prior to his arrest, he was in the news earlier this year following raids on multiple properties last March; and a video of him attacking his ex-girlfriend Cassie appeared on CNN in May.

Combs, who will spend Christmas in custody, has pleaded not guilty to the charges against him as his May 5, 2025 trial date approaches.

Combs was pictured in his senior yearbook taken from Mount St. Michael Academy in Mount Vernon, New York in 1987

Diddy: The high school years

Combs’ mother Janice Combs “had to work extra jobs to pay the bills” to pay tuition for the educational institution, according to a February 2001 piece from the Daily news from New York.

Among the images, from 1987, Combs can be seen surrounded by friends at school, in one case wearing a Boston Red Sox baseball cap. (In later years, he was often depicted wearing a cap of the Red Sox’s chief rivals, the New York Yankees.)

In another shot, the Coming Home artist wore a current ’80s ensemble of a gray sport coat with a red tie.

Combs was pictured in a black tuxedo and bow tie during his final yearbook photo from Mount St. Michael Academy in Mount Vernon, New York in 1987.

“It was a great experience, but it could have been better,” reads a quote from Combs beneath the black-and-white photo, which previously appeared on Reddit in 2017.

Combs spent three years on the football team, one year on the track and field team and was involved in the school’s blood drive his senior year, according to the yearbook.

In another image, Combs wore a jersey with the number 22 during his time as a member of the school’s varsity football team.

He told it The New York Times in a February 2012 interview, he said he was confident in his abilities as a young athlete but was ultimately derailed by injury.

“I just knew I was going to be a pro NFL player,” Combs said, adding that he suffered a broken leg in his “final year of football.”

The school is located approximately 25 miles north of Diddy’s current residence at the Metropolitan Detention Center, Brooklyn

Combs wore a jersey with the number 22 during his time as a member of the school’s varsity football team

The Last Night rapper wore a current ’80s ensemble of a gray sport coat with a red tie as he posed with friends

Combs, who performed in the 2004 Super Bowl halftime show and is best remembered for Janet Jackson’s wardrobe malfunction, said of his athletic ambitions, “That’s not what God had planned for me.”

Mount St. Michael Academy said in 2009 on its website that its football program “traditionally plays one of the most competitive schedules in New York City and has won four CHSFL City Championships” as part of “the Catholic High School Football League.”

The school said it is “proud of its winning tradition, both on the field and in the classroom” and “has a great tradition that builds character, pride and confidence in the student-athlete.”

“Success, in the classroom and on the playing field, is the goal of the Mount St. Michael student-athlete. Quality education and a competitive football experience provide Mount students with the values ​​and opportunities that will last a lifetime.”

In addition to Combs, the school has a number of notable alumni, including The Wire star Andre Royo and the late NFL player Art Donovan.

Some former students of the school, like Combs, have made headlines for their legal issues, including A Bronx Tale star Lillo Brancato and Jersey Shore star Ronnie Ortiz-Magro.

The rapper I’ll Be Missing You was pictured in 1987 surrounded by friends at school

The New York City native wore a Boston Red Sox baseball cap in this ’80s shot

Richard Tricario, the late academic dean of Mount St. Michael Academy, spoke to the Daily News in 2001 about Combs’ time as a student in the 1980s.

“He wasn’t a 2:30 a.m. kid who was quiet all day and then ran straight home — he was active in sports,” Tricario said. “Average” is the word that describes him.”

Tricario, who died in September 2023, told the newspaper that Combs returned to the school in 2000, years after becoming an international celebrity.

“Last year he stopped by the school for a football game on Saturday, accompanied by a TV crew,” Tricario said. “The school did not announce his visit to the students in advance because he was afraid he would attract a troublesome crowd from outside the school.

‘The school is located on a beautiful campus in a middle-class neighborhood. It’s about sports, not about the theater club. Most children go to university. A sign in a door of the school reads: “The city streets stop here.”