Harry Winks walked through the door at Tottenham Hotspur 20 years ago, but his time at the north London club looks to be finally coming to an end.
The arrival of Yves Bissouma last week has accelerated Winks' expected departure, with the club not willing to sell Pierre-Emile Hojbjerg, Rodrigo Bentancur having only joined in January and Oliver Skipp signing a long-term new deal just a couple of months ago. Winks needs regular football this coming season, particularly if he holds any hopes of getting back into Gareth Southgate's England squad ahead of the winter World Cup in Qatar.
Everton tried to prise the 25-year-old away in January, both before and after Frank Lampard's arrival that month, and are attempting again this summer. Their problem lies in their Financial Fair Play struggles and the Toffees reportedly would prefer a loan move initially unless they can move others on first.
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If, or more likely when, the midfielder leaves Spurs this summer there will be a certain sadness about it all. Winks is Tottenham Hotspur through and through, having grown up a fan and been part of the club's academy since he was just five-years-old.
Mauricio Pochettino immediately saw a talent in the player when he arrived in 2014 and Winks would later say that the Argentine walked in on the then 18-year-old as he was signing his first professional deal with academy head John McDermott: "He came in and shook my hand and he said, and I don’t know if he was being truthful or not, 'I have seen your videos, and I told John to sign you up straightaway'. I was gobsmacked at the gaffer just saying that."
Pochettino took his time in nurturing Winks. In his first season the teenager travelled with the team everywhere but didn't play, other than three minutes in the Europa League. The next season was similar, albeit with 17 minutes given to him in the European competition across two substitute appearance.
Winks did not want a loan move away though. His only thought was to play for his club Tottenham Hotspur and it was a pre-season tour to Australia in the summer of 2016 when he showed Pochettino he was ready in matches against Atletico Madrid and Juventus. The regular appearances duly came in the Premier League in the months ahead, with 33 appearances across all competitions until an ankle injury late in the campaign.
Pochettino had noticed him but the 2017/18 season was when the Premier League and Europe started to take note of Winks, with two eye-catching performances against Real Madrid in the Champions League, looking entirely at home up against Luka Modric and Toni Kroos and drawing praise from the Spanish media. He also impressed against Borussia Dortmund and against the likes of Liverpool in the Premier League among many other noteworthy displays before another ankle problem derailed his season. The ankle pain would likely remain for the rest of his career, with Pochettino telling football.london in those days that the midfielder just had to learn to manage it throughout his playing days as many players do with certain problems.
The Argentine knew that if Winks could do that then he would become a top Premier League player. Pochettino called him his 'Little Iniesta' behind the scenes at Spurs and said publicly: "His characteristics are perfect. When we talk about midfielders like Xavi and Iniesta, he's like this type of player. He has this capacity but he needs to take my words in a very positive way - he needs a lot of work. I don't want to praise him too much because if so his head [grows big]! His perception will be 'wow!' And the reality is he still needs to prove [himself].
"He has the possibility and the potential, of course, but now it is up to him and we go again: mentality. In his mind he is capable to learn about suffering: there never is enough training, always try to be better. Football must be his focus, not the business around football.
"Maybe [if he learns this] he will play at a very good level and be one of the best midfielders in England. If he wants to take my advice, take it. If people don't want to take it, we cannot help, but of course his potential is to be a very, very good player for England and Tottenham. First for Tottenham and then, if England believe that he can help them, for England, too."
With Mousa Dembele struggling with injury in the 2018/19 season and eventually leaving that winter for the Chinese league, which would be kinder on his body, Winks, along with Moussa Sissoko, stepped up as an unfancied duo and helped take Spurs to the Champions League final and another top four finish in the Premier League.
In that 2019 Champions League final against Liverpool much was made of Harry Kane struggling on the night in Madrid after being out for a couple of months. Few pointed out that behind him Winks had played well in the centre of the pitch for more than an hour in his first game after almost three months out following groin surgery.
Winks did play for England, appearing 10 times and scoring once, and initially he was hailed as the answer to the country's problems in midfield following his man of the match debut in 2017 against Lithuania.
In the months after the Champions League final, Southgate's assistant manager Steve Holland said of Winks: "He is a player that we have very much been waiting for in that kind of position. Someone who is comfortable to turn and connect the play when we are working through the offensive phases. Quite simply, had he been fit and consistently playing for Tottenham, he would have been in the squad [for the Nations League] 100%. It is just a call we had to make. I am sure he will acquire many England caps in the future."
In the season after Pochettino's departure things started to sour at Spurs for Winks. Jose Mourinho played him after succeeding the Argentine, even handing him the captain's armband for a Premier League match at Wolves. However, something changed the following campaign with starts hard to come by and Winks was occasionally left out of matchday squads entirely. It was only Ryan Mason's caretaker spell that brought him back into the team in the league.
The problem for Winks is that he lost his rhythm with his appearances so infrequent, and he began to mistakes and his form dropped. With that so the fans began to turn. Being 'one of their own' mattered little as their frustrations grew and with so little time to impress, the player sensed his time might be coming to an end at Tottenham.
When asked whether he could make sense of his dramatic fall from Spurs and England star on the rise and Champions League starlet to turning out for the club's second string in a Europa Conference League defeat at Vitesse Arnhem, Winks said: "No. No, I can’t, but listen, the circumstances are that I’m in this situation. Of course [my confidence is low]. When players are not playing well and you only have yourself to blame, it’s difficult. I want to be at my best, firing and playing really well. It comes with games, but ultimately it comes with me performing on the pitch when I get the opportunity.
"If I’m not doing that, then I only have myself to blame. I’m man enough to admit that I need to improve in certain areas. On the contrary, I need to play games and the only way to [improve] is getting minutes and getting that sharpness back."
He added: "I love Tottenham, I’ve always made that clear, but I want to play football, and I want to play regular football. The only way to play your best football, get momentum is playing regularly. I’m giving my all for the club, of course I am. They stuck by me, I stuck by them – and I want to play for Tottenham, but it is difficult when you get matches here and there, confidence is low and you don’t get that run of games."
When Antonio Conte arrived in N17 he sparked something of a revival for Winks, handing him eight Premier League starts from his first 15 matches. The Italian made it clear that he would not allow the midfielder to leave in the January transfer window because he could "count" on him.
Early in the window he set that stance, declaring in a press conference: "Winksy showed to be a reliable player. Winks will stay here. Winksy showed that I can count on him."
From March onwards, however, Winks found his game time reduced to substitute minutes here and there as Bentancur and Hojbjerg became the midfield duo of choice for Conte with Skipp out injured.
Now with the latter's return as a young player Conte has high hopes for and the arrival of Bissouma, Winks finds himself fifth choice in the pecking order. Everton would be a good move for him and others have shown interest, Crystal Palace believed to be among them.
When Winks does leave Tottenham after making 202 appearances for the club he has always loved, he deserves much more than the goodbye he is likely to get.
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