Sir Alex Ferguson named Ralph Milne as his least successful signing during his time at Manchester United.
Ferguson, who took charge at Old Trafford in 1986, quickly rebuilt the squad with key players like Brian McClair, Steve Bruce, and Mark Hughes, eventually leading the club to multiple Premier League and cup triumphs.
Manchester United legend reflects on early transfer regrets
In 1988, Ferguson signed attacking midfielder Ralph Milne from Bristol City for £170,000.
Despite previous success with Dundee United, Milne struggled with form and personal issues, including alcohol and gambling problems, which affected his performances at United.
He made 27 appearances in his first season, scoring three goals, but was soon relegated to the reserves and played his last professional game at just 28.
Ferguson admitted years later that this early decision remained a source of criticism: “My worst signing? Ralph Milne. I only paid £170,000 but I still get condemned for it.”
Milne’s later life included health and legal challenges, and he passed away at the age of 54 in 2015.
Despite this setback, Ferguson’s tenure at United remained iconic, as he navigated the evolving transfer market and transformed the club into one of the most dominant sides in football history.
