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#3 Diego (Werder Bremen to Juventus)
Juventus signed Diego from Werder Bremen in 2009 for about €25m after the Brazilian impressed at the Bundesliga club for three seasons.
The midfielder scored 54 goals during his time at Bremen, winning multiple individual accolades, including the Bundesliga Player of the Season award in his debut campaign.
Arriving at Juventus to fill in for the retiring Pavel Nedved, Diego soon got down to work. He had an assist and two goals to his name in his first two league games. However, his sensational form at Juventus petered out rather too quickly. Falling out with then-manager Ciro Ferrara soon sealed his fate, as he was placed on the transfer list months after joining the club.
Diego scored just seven goals in his 44 appearances for the Turin club before moving back to Germany to join Wolfsburg for nearly half the price Juventus paid for his services.
In reality, Diego's Juventus spell all but heralded a downward spiral in what could have been a very promising career.
#2 Moise Kean (Juventus to Everton)
Moise Kean was promoted to Juventus' first team in the 2016-17 season after scoring 24 goals in 25 games for the youth team in the previous campaign.
However, as he did not get much game-time, Kean was sent out on loan. That came after he became the youngest player (16 years) to make their Juventus debut.
The Italian striker returned to Turin after a season-long loan at Verona. He came alive in Juventus' famous black and white, scoring seven goals in just six starts.
Kean established himself as one of Europe's most promising talents, and many expected Juventus to do everything possible to keep him. However, at the end of the campaign, he was shockingly sold to Everton for €27.5m, where he has endured a torrid spell.
He is currently on loan at PSG. The 21-year-old has picked himself under Mauricio Pochettino, scoring 15 goals in 29 games for the French club.
#1 Nicklas Bendtner (Sunderland to Juventus)
Nicklas Bendtner's deadline day move to Juventus from Sunderland in 2012 was something close to a FIFA career mode transfer, as it left many scratching their heads as to why and how it happened.
In his defence, Bendtner scored a moderate eight goals for Sunderland the season before. But that shouldn't have been enough for him to secure a loan move to a European powerhouse like Juventus.
The Dane was hardly used at Juventus as his playing time was limited due to injuries.
Even when he was injured, Bendtner was involved in some off-field controversies.
At the end of his loan spell in Turin, he had made only 11 appearances for the Turin club and scored no goals.
Despite having an option to buy in his contract, Juventus expectedly declined to do so, prompting further questions why the Dane was signed in the first place.
