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#3 Federico Fazio
Most Serie A and La Liga fans would know Federico Fazio as a successful defender, but the same could not be said about the Tottenham Hotspur faithful. The north London club signed him for €10 million in 2014 which initially felt like quite a bargain.
The Argentine had become a mainstay in the Sevilla backline for many years and was also capable of producing the odd goal. However, Fazio failed to effectively adjust to the intensity of the Premier League and was always caught out by the lack of pace.
Tottenham Hotspur soon signed Toby Alderweireld and Kevin Wimmer, which meant no opportunities for the former Sevilla centre-back. He may have helped the La Liga club to the 2014 Europa League crown, but it was evident that he wasn't going to help the Lilywhites get any closer to silverware than they already were.
After making 32 appearances for Tottenham Hotspur, the Argentine joined Roma in a deal worth €3.2 million and established himself as a pillar at the heart of their defense. He delivered one of his finest performances on a historic night when Roma knocked out FC Barcelona from the 2017-18 Champions League.
#2 Vincent Janssen
Still only 27-years-old, Vincent Janssen once looked like he had the world at his feet and a great potential ceiling, but those days are gone. He is now plying his trade in Mexico in Liga MX, where he has been bang average. But when the Lilywhites took the risk of splashing £19.80 million for his signature in 2016, a few protested.
After all, this was a striker who, despite not representing Ajax, Eredevisie's most potent side, had taken the Dutch league by storm. In 34 games, he had scored 27 times and provided a further five assists. This tally with AZ Alkmaar made him the youngest player since Ronaldo Nazario (PSV Eindhoven) to score 25 or more league goals in a single league campaign.
As a result, he was awarded the 'Johan Cruyff Young Talent of the Year' award. Janssen had proven his worth and that he was ready for the top European leagues, and Tottenham Hotspur obliged. That was the beginning of the end.
The left-footed forward never looked comfortable in England and lacked serious confidence. He missed opportunities, easy ones that he was expected to take and failed to deliver. Fans quickly forgot he was in their ranks when he became a fringe player and was ultimately let go.
Janssen scored only two goals in 31 Premier League appearances and the north London club still somehow managed to sell him for €9 million to Monterrey.
#1 Roberto Soldado
Having built his reputation as an elite striker in Spain, Roberto Soldado arrived at Tottenham Hotspur in the summer of 2013. Gareth Bale's departure to Real Madrid left a handsome amount in the club's kitty as they went on a shopping spree of sorts.
The Spaniard signed for a club record fee of €30 million. However, a few days later, Tottenham Hotspur forked out more money to make Erik Lamela their most expensive signing. Soldado arrived in England at the zenith of his career as a typical No.9, a goalpoacher with a midas touch.
In his previous three La Liga campaigns, he had scored 24, 18 and 17 goals respectively. So the idea was simple, a 20-goal-a-season striker will come to the north London club and propel them closer to major silverware. But his performances in a Spurs shirt once again reminded fans that the Premier League is different than most other leagues.
Soldado lacked the physicality to adjust to the English top-flight and that was his biggest roadblock. He was clever with his movement but once the defender caught up, the centre-forward could not hold his ground. In his first season at Tottenham Hotspur, he managed 11 goals in 36 appearances, quite poor by his standards.
Fans were positive and thought the adjustment period was over and the former Mestalla striker would get into the act. But the following season was even more disappointing as Soldado produced five goals and six assists in 40 games across all competitions.
The verdict was out, he was an absolute flop and wasn't meant to make the cut and lead the line for a top Premier League club.
