#2 Cristiano Ronaldo (Age: 18)
In 2003, the future 5-time Ballon d’Or winner walked the halls of Highbury with Wenger in tow. The two spoke about what Ronaldo’s role would look like at Arsenal and his trajectory towards becoming a formidable winger.
By the end of the visit, Ronaldo walked out of Highbury with an Arsenal jersey with his name on the back. With a bid of €4 million already accepted by Sporting Lisbon, the winger only had to agree to personal terms.
Yet in the waning hours, the Portuguese coach Carlos Queiroz - who was Fergie’s assistant at the time - convinced the young gun to play at Old Trafford. After an impressive friendly against United, the Manchester club promptly made a bid of £12 million for the youngster’s services.
The pairing of Henry and Ronaldo surely would've yielded trophies from all over Europe, yet sadly, the mouth-watering tandem would never be.