Roy Keane: From Record Signing to Legendary Captain
In the summer of 1993, Sir Alex Ferguson sought to strengthen a midfield that had just secured United's first league title in 26 years. Nottingham Forest's relegation made their tenacious 21-year-old midfielder, Roy Keane, one of the most coveted players in English football. Keane seemed destined for Blackburn Rovers, but when paperwork wasn't submitted in time, Ferguson discovered the delay and called Keane directly, arranging a meeting that hijacked the transfer.
United paid £3.75m, smashing their previous record fee for Gary Pallister in 1989. The investment proved immediate as Keane became the team's heartbeat, forming formidable midfield partnerships with Paul Ince and later Paul Scholes. His leadership was invaluable as United dominated the 1990s and early 2000s.
Keane was handed the captain's armband in 1997 and claimed seven Premier Leagues, four FA Cups, and the Champions League. By his bitter departure in 2005, he had played 480 games, cementing his place as arguably United's greatest-ever captain.
Andy Cole: The £7m Goal Machine
Keane held the club record for about 18 months. In January 1995, Ferguson returned to the market to sign Andy Cole from Newcastle United in a deal valued at £7m (£6m cash plus Keith Gillespie valued at £1m), breaking the British transfer record. Cole's clinical scoring continued at Old Trafford.
His legacy was immortalised through his partnership with Dwight Yorke from 1998, and the duo were crucial in United winning the Treble in 1998/99. Cole left in 2001 and retired in 2008 with 289 official club goals, 121 of which came in a United shirt.
Angel Di Maria: The £59.7m Flop
After a dismal seventh-place finish under David Moyes, United rebuilt under Louis van Gaal in summer 2014. Desperate for a world-class winger, they targeted Real Madrid's Angel Di Maria, fresh from a Man of the Match display in the 2014 Champions League final and helping Argentina reach the World Cup final. United shattered the British transfer record again, paying £59.7m and handing him the famous No.7 shirt.
The move initially seemed a masterstroke as Di Maria scored three goals and provided four assists in his first six games. However, Van Gaal's rigid, possession-focused approach stifled his creativity, sparking tension. Off the pitch, an attempted break-in at his Cheshire home left his family shaken and desperate to leave England.
As the season wore on, Di Maria was dropped to the bench, finishing with only four goals. He refused to join United's pre-season tour to the US and was sold to Paris Saint-Germain at a financial loss, becoming one of Old Trafford's most expensive flops.
