Some footballers are remembered for their goals, others for their leadership, and then there are those who find a way to leave their mark off the pitch.
David May falls into that last category.
On May 26, 1999, Manchester United achieved one of the most dramatic victories in Champions League history, completing their legendary treble.
The night belonged to United, but somehow, May made sure it belonged to him too—without even playing a single minute.
The Man in Every Photo
While the likes of Teddy Sheringham and Ole Gunnar Solskjær secured the last-gasp win over Bayern Munich, May was making history in a different way.
As the celebrations kicked off, there he was—front and center, towering over teammates, leaning on David Beckham, and making sure he was in every photo with the trophy.
Even his teammates couldn’t help but laugh. United defender Jaap Stam later joked in his autobiography that May had mastered the art of being in the right place at the right time—at least when the cameras were rolling.
A few months later, an English magazine took things a step further by hilariously photoshopping May into history’s most iconic pictures.
He had officially become a legend of the celebrations.
The Prankster of the Dressing Room
May wasn’t just known for his photo-bombing skills.
In the dressing room, he was the team’s notorious prankster.
He took pride in lighthearted antics, from sneaky showers pranks to lacing teammates’ gear with Deep Heat.
His mischievous nature may have made him the subject of many jokes, but he was also a respected squad member who played an important role in the club’s treble-winning season.
Though injuries limited his appearances, May featured in some of the campaign’s most critical games, including the final-day Premier League victory over Tottenham and the FA Cup final win against Newcastle.
He may not have played in the Champions League final, but he still saw himself as part of the team’s success.
A Medal That Meant Nothing
Despite being part of United’s historic triumph, May had a surprising take on his Champions League medal.
Speaking on the Greatness on Demand podcast, he admitted that the medal itself held little value to him.
“The game was unbelievable,” he said, “but the actual medal doesn’t mean anything, because I was injured.
I never kicked a ball in the Champions League.”
While many players might have clung to the silverware, May valued the moment itself far more than the prize.
His winning mentality and self-awareness showed that he was more than just a jokester—he was someone who understood the significance of hard work and sacrifice.
A Footballing Journey Shaped by Family
May’s work ethic didn’t come from nowhere.
Growing up in Oldham, Lancashire, he was raised by a father who instilled discipline and resilience in him.
His dad, a former policeman, had once been a promising footballer himself but was unable to pursue the sport due to circumstances beyond his control.
That unfulfilled dream became May’s motivation.
When teenage distractions came knocking, his father’s words stuck with him: “If you want to do it, do it. But if you want to get there, sacrifice.”
May took that advice to heart.
While his older brothers had talent but lacked the same drive, he spent countless hours honing his skills in a small yard, kicking a ball against a wall over and over.
That relentless practice paid off when he signed his first professional contract with Blackburn Rovers in 1988 at the age of 18.
The Call That Changed Everything
May was a solid, reliable defender, but even he was shocked when Mark Robins, then at Norwich, casually mentioned that Manchester United had been keeping an eye on him.
At first, he thought it was a joke. Then, United’s chief scout Les Kershaw introduced himself and delivered a life-changing message: “Alex Ferguson wants to sign you.”
The move wasn’t all smooth sailing, though.
Blackburn accused him of being greedy during contract talks, despite May only requesting a fraction of what club star Alan Shearer was earning.
Then there was his teammate, David Batty, who was less than thrilled about May’s potential move to United.
During an away trip, Batty repeatedly prank-called May’s hotel room, whispering, “Scum, scum, scum” down the line. It wasn’t exactly a warm send-off.
Life at United: Trophies, Pranks, and Injuries
Once at Old Trafford, May quickly realized he was surrounded by legends.
At first, he felt out of place, but over time, he carved out a role for himself.
Injuries limited his game time, but he still collected an impressive haul of trophies, including two Premier League titles, two FA Cups, and, of course, the Champions League.
His playful side never faded. He became known for his pranks, like rigging a bucket of water to flood Paul Parker’s hotel room. Even though he denied it, everyone knew it was him.
But football doesn’t last forever, and when his contract expired in 2003, reality hit hard.
The Struggles After United
Leaving Manchester United wasn’t easy.
May admitted that he felt like his world had collapsed.
He found himself at a loss, struggling to figure out his next move.
After a farewell party at an upscale bar in Manchester, he walked home alone, carrying a £300 bottle of champagne.
A homeless man sitting on a park bench noticed. “What have you got there, pal?” he asked.
“A bottle of champagne,” May replied.
“Are we opening it?” the man asked.
May hesitated for a second before shrugging. “Yeah, go on then, f*** it.”
That moment led to a 12-day drinking spree before he eventually broke down in his wife’s arms. It was a tough period, but he found his way back.
Life Beyond Football
May went on to play briefly for Burnley before finishing his career in non-league football.
After retirement, he tried his hand at various ventures, including the wine business, media work with MUTV, and his true passion—fishing.
Through it all, his personal mantra has remained unchanged: “Never accept defeat. If you want it, go and get it.”