2. Ryan Sessegnon
While I hate to admit it, Ryan Sessegnon hasn’t lived up to his £24.3 million transfer fee. In fact, he’s come about as close as Arsenal did to winning the Premier League last year. The young Englishman has shown glimpses lately of his potential capabilities, but otherwise has disappointed since arriving at Tottenham from Fulham in 2019.
Plagued by a litany of injuries, Sessegnon’s progress is seemingly forever impeded by his pre-disposition to pulling up lame. Sent out on loan to 1899 Hoffenheim last season, Sessegnon missed over a month there with yet another ailment.
It wasn’t as if Spurs didn’t know about Sessegnon’s injury woes. Pochettino and company purchased the player while he was on the treatment table after sustaining a serious hamstring injury in the European Under-21 Championship in June 2019 against Romania. He didn’t make his first appearance with Spurs until Nov. 3, almost five months later.
Sessengon missed some time in the current campaign through injury, too, and has just returned to senior action. While he is showing slow signs of progression under Antonio Conte, it’s not nearly enough to consider his move, so far anyway, as anything but a failure.