Amid what’s been the most challenging year in the life of music mogul Sean ‘Diddy’ Combs, Dailymail.com is taking a look back at simpler times for the rapper, when he was 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, which is about 25 miles north of his current whereabouts at the Metropolitan Detention Center, Brooklyn.

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

Among the claims is that he persuaded women to participate against their will in group 𝓈ℯ𝓍ual exhibitions referred to as ‘Freak Offs.’ Combs, who is also charged with transportation to engage in prostitution, has made a trio of attempts in vain to be granted bail, amid concerns from the court he would attempt to flee or tamper with his case.

Prior to his arrest he was in the headlines earlier this year after raids on multiple properties this past March; and video of him assaulting his ex-girlfriend Cassie surfacing on CNN in May.

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

Diddy: The High School Years

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

Among the images, dated 1987, include Combs surrounded by friends at the school, in one case, donning a Boston Red Sox baseball cap. (In later years he was frequently pictured donning a cap of the Red Sox chief rivals, the New York Yankees.)

Another shot featured the Coming Home artist donning a timely 1980s ensemble of a grey sport coat with a red tie.

Combs was pictured in a black tuxedo with bow tie his senior year yearbook shot from Mount St. Michael Academy in Mount Vernon, New York in 1987.

‘It was a great experience but it could have been better,’ a quotation from Combs read under the black and white picture, which was previously published on Reddit in 2017.

Combs was active on the football team for three years, track team for one year, and 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 The New York Times in a February 2012 interview that he was confident in his abilities as a young athlete, but was ultimately derailed by an injury.

‘I just knew I was going to be an NFL pro player,’ Combs said, adding that he suffered a broken leg in his ‘last year of football.’

Combs, who performed in the 2004 Super Bowl halftime show most remembered for Janet Jackson’s wardrobe malfunction, said of his athletic ambitions: ‘That isn’t 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’s ‘proud of its winning tradition both on the field and in the classroom’ and ‘has a great tradition which 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. A quality education and a competitive football experience provides Mount students with the values and opportunities that last a lifetime.’

Aside from Combs, the school boasts a number of notable alums, including The Wire star Andre Royo and 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.

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

‘He wasn’t a 2:30 kid who was quiet all day, then ran home right away – he was active in sports,’ Tricario said. ‘”Average” is the word to describe him.’

Tricario, who died in September of 2023, told the paper that Combs had made a return to the school in 2000, years after becoming an international celebrity.

‘He stopped at the school last year for a Saturday football game, accompanied by a TV crew,’ Tricario said. ‘The school did not announce his visit to the student body ahead of time, worried that he might draw a tough crowd from outside the school.

‘The school sits on a fine campus in a middle-class neighborhood. It is big on sports, not the theater club. Most of the kids go on to college. A sign inside one door of the school declares, “The City Streets Stop Here.”‘