1. Hugh McLenahan - Three Freezers full of Ice Cream
Valued at over $3 billion, Manchester United are described by Forbes Magazine as by far the most valuable sports team in the world. The extent of their financial clout is such that a summer in which they spent £28 million is deemed to be so disappointing that they are likely to have a budget of over £50 million come the January transfer window. Things were not always that way, however, and nowhere is the discrepancy between modern transfer fees and pre-war ones more apparent than in United's 1927 signing of Stockport County wing-half Hugh McLenahan. With Stockport struggling financially and United Assistant Manager Louis Rocca the owner of an ice cream business, it seemed obvious in the logic of 1920s transfers that the appropriate thing would be for United to donate some of Rocca's ice cream to a Stockport fundraiser. Three full freezers later and McLenahan was a Man United player. To put that in context, paying in ice cream for Fellaini would have set the Red Devils back 55 million Cornettos, while their £80 million sale of Cristiano Ronaldo would have made them 96 million Magnums.
How did he do? McLenahan joined during an era that was not the most glittering of Man United's illustrious history. He stayed at the club for a decade, during which time they finished last in the First Division in 1931 and dropped to their lowest ever league position in the Second Division in 1934. A decent utility player, McLenahan never really established himself as a regular in the first team and, after playing 116 games for the club, was sold on to Notts County after United were promoted back to the top flight in 1936. Unfortunately United didn't throw in a couple of Viennettas to sweeten the deal.