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1. Wayne Rooney - Everton to Manchester United (£25.6 million, 31st August, 2004)
Despite being England's and Manchester United's all-time top scorer, Wayne Rooney, and not Ravel Morrison, is the biggest disappointment to have emerged from both camps as Morrison was a bright talent at youth level. Rooney, on the other hand, was thought to be a better all-round player than Cristiano Ronaldo during their formative years at Manchester United.
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Having joined Everton's academy aged 9, Rooney made his first-team debut against Tottenham in a 2-2 draw. He was booed by Spurs' fans who chanted 'Who are ya?' whenever he was in possession. Just over two months later, Rooney let them know he was as he scored the winner against Tottenham's arch-rivals Arsenal, ending their 30 match unbeaten run. After the match, Arsene Wenger, known for having an eye for world-class talent, said that Rooney was the biggest talent he'd witnessed during his time in England thus far.
After spending another season at Everton and starring at Euro 2004, Rooney then joined Manchester United scoring a hat trick on his United and Champions League debut against Turkish outfit Fenerbahce. Rooney spent 13 years at the Old Trafford club winning every possible trophy on offer, ending with 5 Premier League titles, 4 Community Shields, 3 League Cups (now known as the Carabao Cup), and the 2016 FA Cup, the 2008 UEFA Champions League, the 2008 Club World Cup and the 2017 Europa League scoring 253 goals (including 183 in the Premier League, the most by a player for a club) and garnering 103 assists (third-most in the Premier League) in the process.
At the conclusion of the 2016-17 season, he moved to back to boyhood club Everton for a season before making the across the pond to DC United. 18 months, 48 appearances, 23 goals and 15 assists into his contract, he decided to move back to England with EFL Championship side Derby County, with the contract beginning on 1st January, 2020 and a possible player-coach role in the offing.
