Dele, the subject of a mesmerising piece of transfer business when Tottenham Hotspur acquired him in February 2015, had the world at his feet, but something went wrong somewhere along the line.
In the final hours of the 2015/16 winter window, Spurs announced the signing of 18-year-old Dele from League One side Milton Keynes Dons for a fee of just £5 million, with the Englishman set to remain in Buckinghamshire until the end of that season.
It was a move that raised eyebrows - a relatively significant fee for a player not many had heard of. However, those who knew of the now 28-year-old realised it could be a mastermind move from Tottenham, and boy was it!
He made his senior debut as a 16-year-old against Cambridge United in the Emirates FA Cup, scoring his first-ever professional goal in the replay, and went on to find the back of the net on another 23 occasions, as well as contributing to 15 assists in 88 appearances for MK.
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Early times in the capital
After a full pre-season, where he wowed the likes of Real Madrid with his performance against their midfield, which included legends Toni Kroos and ex-Spurs man Luka Modric, his first eyebrow-raiser at his new club came on match day three of the Premier League season.
After coming off the bench to play the remaining 25 minutes at the King Power Stadium, Dele was waiting at the back post to slide in and head the ball past Kasper Schmeichel to earn The Lilywhites a point against the eventual title winners Leicester City - the first of his many top-flight goals.
He had an outstanding breakthrough season in North London, scoring ten goals and registering ten assists in 46 appearances, with the 19-year-old, as he was at the time, also being named the PFA Young Player of the Year in his first-ever campaign at the pinnacle of English football and he was a part of the PFA's Premier League Team of the Year.
Alongside this, he won the Premier League Goal of the Season Award for an outrageous volley at Selhurst Park, where he chested the ball down, flicked it over current Spurs Assistant Coach Mile Jedinak's head and then slammed an effort past Wayne Hennessey.
After a spectacular breakthrough season under Mauricio Pochettino, he was at the forefront of the Tottenham side as they went head-to-head with Antonio Conte's Chelsea for the title the following term.
He scored a staggering 18 goals in the Premier League, where he also registered eight assists, additionally, he was involved in another eight goals with contributions in both the UEFA Champions League and the run to the semi-final of the FA Cup.
In April, he scored the penultimate goal in a White Hart Lane North London Derby, with Tottenham pipping Arsenal to a 2-0 victory.
For the second year in a row, he was named in the PFA's Premier League Team of the Year, as well as adding another PFA Young Player of the Year title to his name. He became the fourth-ever player to achieve this in consecutive seasons and the first Spurs to win it since Gareth Bale in the 2012/13 season.
His form continued into the 2017/18 campaign, where he scored 14 and assisted 15 across all competitions. However, arguably his best moments came at Wembley Stadium, with the first taking place in November. Just under a year on from scoring his first Champions League goal on his debut in the competition, he scored a brace and powered The Lilywhites to a terrific 3-1 win against reigning European champions Real Madrid - a side which included the likes of Cristiano Ronaldo, Sergio Ramos, Karim Benzema and Marcelo.
In April of that season, he scored another crucial goal at Wembley, this time in the FA Cup semi-final as he put Spurs 1-0 up against Manchester United, however, a fightback from The Red Devils saw Pochettino's side crash out.
The 2018/19 season is when it all started to crumble for Dele. Once a teenage sensation, the now 22-year-old was facing the first setback of his Tottenham career and had to figure out a successful way of dealing with this.
After an incredible FIFA World Cup tournament, he was expected to return to North London and deliver the goods once again, but he missed a large portion of the season with hamstring issues and only scored eight times, assisting seven goals in the process.
A rather inconsistent year led him into the palms of Jose Mourinho, who in his first few days at the club told Dele: "I understood already that you are a f*****g lazy guy in training," in front of the rest of the squad, as seen in the 'All or Nothing' documentary published by Amazon Prime Video.
However, at the start of the Mourinho era, the attacking midfielder scored four and assisted three in the first seven games, seemingly not letting his new boss' comments affect him. But, with a suspension and injury during 'Project Restart' after the COVID-19 pandemic, he found himself falling down the pecking order and out of favour.
That carried over the next two seasons, even once Mourinho was sacked towards the end of the 2020/21 campaign and under Nuno Espirito Santo and Antonio Conte when they took over in July 2021 and November 2021, respectively.
Despite being given chances in both the UEFA Europa League and UEFA Europa Conference League, his chances in domestic competitions were limited. He appeared just 25 times in the Premier League for Tottenham between September 2020 and January 2022, before he moved to Everton on a free transfer, bringing his time in North London to an emotional end.
When Dele sat down for a heartbreaking interview with Gary Neville on Sky Sports' 'The Overlap' podcast, he spoke about the harrowing stories from his childhood and the personal struggles he faced when at Tottenham.
In the interview, which was released in July 2023, the Englishman fought back tears as he revealed that he had just come out of an American rehabilitation centre a month prior due to a sleeping pill addiction, as well as struggles regarding his mental health.
The former Spurs midfielder also discussed his traumatic childhood, which saw him adopted by the Hickford family - Harry Hickford eventually became Dele's agent, showing just how much of an impact the family had on his life.
During the conversation about his childhood, which left both Dele and Neville in tears, he revealed to the world that he was 'molested' by his mum's friend and was "sent to Africa to learn discipline, and then I was sent back." He also stated that he was smoking and dealing drugs by the age of just seven and at eleven he came inches from death when he was hung off a bridge by a man.
Recapping his time in N17, the former MK Dons youngster said that the toughest moment for him came when Mourinho stopped playing him.
"I remember I was in a bad place and I just looked in the mirror asking if I could retire now at 24 doing the thing I love. That was heartbreaking for me, to even have that thought, that hurt me a lot and was another thing I had to carry."
Whilst he said he doesn't blame anyone but himself for the downfall of his Tottenham career, there is no doubt that these huge personal issues would have taken a toll on his life, both away from football and at the club.
"I don't blame Mourinho, I don't blame anyone. My reaction to that wasn't right, but it wasn't something I had control over."
Whilst things never worked out for him with The Toffees, nor on his loan with Turkish Super Lig giants Besiktas, Dele has now found his feet as he attempts what would be a spirited and sensational comeback to the very best of his game.
He joined Italian side Como in the 2025 January transfer window, a side managed by former Barcelona midfielder Cesc Fabregas and includes ex-stars such as Pepe Reina and Sergi Roberto.
If he can get back to his old levels, there will be a new monster unlocked.
