Manchester United's fans can take solace from the fact that, with a couple of notable exceptions, the Scot's judgment tends to be flawless.
Eric Cantona (Leeds, £1.2 million, 1992) Success Rating: 10/10
Sir Alex Ferguson famously chanced his arm asking Howard Wilkinson about the troublesome Frenchman, brought him across the Pennines for a cut-price fee and accidentally signed one of United's all time greats.
Teddy Sheringham (Tottenham, £3.5 million, 1997) Success Rating: 9/10
The Spurs striker was already in his 30s when Ferguson brought him to Old Trafford as an experienced hand to guide his crop of youngsters, but he went on to help United to three titles and, famously, the Champions League.
Dwight Yorke (Aston Villa, £12.6 million, 1998) Success Rating: 7/10
Ferguson smashed United's transfer record to bring the Aston Villa forward to Old Trafford, but his almost telepathic partnership with Andy Cole became one of the most prolific in United's history.
Ruud van Nistelrooy (PSV, £19 million, 2001) Success Rating: 8/10
Another record signing – for a few days at least – came complete with the scorn of Harry van Praag, the PSV chairman, but van Nistelrooy provided a stunning 95 goals in 150 games over five years at Old Trafford.
Juan Sebastian Veron (Lazio, £28.1 million, 2001) Success Rating: 4/10
Ferguson's biggest mistake. Veron failed to settle into the more advanced role the Scot handed him after his British record move and was sold to Chelsea after two underwhelming years for half of his massive fee.
Rio Ferdinand (Leeds, £30 million, 2002) Success Rating: 9/10
For the second year in a row, Ferguson broke the British transfer record to make the former Leeds man the world's most expensive defender. The risk paid off, though, as Ferdinand blossomed into arguably the finest centre back on the planet.
Kleberson (A Paranaense, £6 million, 2003) Success Rating: 2/10
Looked reasonably impressive in Brazil's 2002 World Cup-winning side, but seemed a strange choice as a replacement for Roy Keane.
Cristiano Ronaldo (Sporting Lisbon, £12.6 million, 2003) Success Rating: 10/10
It may look a paltry sum now, but, for an unproven teenager signed on the recommendation of players impressed after a friendly, Ronaldo's fee was comparatively high. He proved to be more than worth it.
(Everton, £25.6 million, 2004) Success Rating: 9/10
Another hefty sum for a teenager with just two complete seasons of Premier League football under his belt, but a hat-trick on his debut against Fenerbahce augured well.
Henrik Larsson (Helsingborgs, Loan, 2007) Success Rating: 6/10
It is hard to categorise the two-month loan which brought the veteran Swede to Old Trafford as a risk. Larsson wanted a swansong in one of Europe's top leagues and, while he hardly set the world alight with his performances, provided invaluable cover and a touch of class as United regain the title.