Aaron Lennon only joined Tottenham Hotspur because of his astronomical Leeds contract - but then he never wanted to leave.

The former winger, whose two former sides meet at Elland Road for Saturday’s early kick-off, rose through the Yorkshire side's academy to become the Premier League's youngest-ever debutant at 16 years and 129 days old - ironically against Spurs in 2003.

However, with Leeds in freefall following relegation, the massive terms of his early deal made a departure unavoidable. He spent the 2004/05 campaign in the Championship after the likes of Alan Smith, James Milner and Mark Viduka were offloaded to generate funds following their drop into the second tier.

Lennon's stint at his boyhood club drew to a close in the summer of 2005, when he made the switch to the north London outfit for £1million. Lennon spoke candidly about the heartbreak of departing Leeds while appearing on the Off The Shelf Podcast.

He said: "Honestly, [it was] a tough, tough decision. I didn't want to leave Leeds. I've been open about this. It's my hometown, I loved it, even though we were relegated to the Championship and in financial difficulties, I still wanted to play for Leeds.

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"They literally told me the money was that bad and my agent told me to meet the guys in London, they told me Daws (Michael Dawson) was coming, Wayne Routledge, Tom Huddlestone and I liked the sound of that, but I struggled for three or four months, I couldn't settle, I was homesick."

Beyond his reluctance to move elsewhere, former Leeds manager Kevin Blackwell previously disclosed that Lennon was actually required to accept reduced wages when putting pen to paper on his Spurs deal. The interim Crawley Town manager stated in 2006: "He actually took a wage cut to go to Tottenham from Leeds.

"The contract that he had was so prohibitive to Leeds - it came from the Premiership days - that there was no way we could afford to keep him." The arrangement saw Lennon pocket £10,000 per appearance, and a substantial £100,000 following every five senior matches.

He shared the complex details of the agreement when appearing on Rio Ferdinand's Five podcast. Lennon informed his former international colleague: "Mine was done quite ruthlessly. Ken Bates came in and to be fair to him, I didn't understand at the time, but my contract was good.

"It was £5,000-a-week, as soon as turned pro, and £10,000 an appearance. The incentives were crazy. It was like every time I played five games I would get £100k. At that time I signed, I was 14. So they are thinking he isn't going to play, there was no money in it unless you played. But then I started breaking in.

"My contract was silly looking back. It was crazy numbers and they were thinking he won't play. But then I started playing. I was on the bench and they couldn't put me on because I was going to hit one of those appearances."

He continued: "Yeah, I remember Gary Kelly going mad and saying our best player is on the bench now. Our most in-form winger is on the bench. I was just sat there and Leeds fans were singing my name. But eventually he put me on because it got that bad with the fans singing my name they had to put me on.

"I think this is the first time it might have come out. I remember at the end of the season Ken Bates told me you are done at this club. Because of the money. It wasn't even in a nice way. And I was like this is my hometown. I was upset and I remember going away and got the call saying they have accepted a bid, you are going to Tottenham."

While he struggled to adapt initially, Lennon soon became part of the furniture at White Hart Lane, spending a decade of his career with Spurs. And it would've been longer had Mauricio Pochettino not pushed him out, as he claims.

He reluctantly joined Everton in September 2015 after Pochettino made him train with the Under-21s and didn't give him a squad number. Continuing on Off The Shelf, Lennon explained: "I was gutted. I knew it was coming because I wasn't playing much and I was out of the squad, but it was tough because I felt I could play in that side.

"This club was like home then, I'd been at Leeds, but this became home... It was tough, I knew it was coming but until it happens you don't realise how hard it hits you."

As for the here and now, Daniel Farke's Leeds head into the weekend fixture without securing victory in their previous five league outings and face an in-form Spurs squad enjoying a three-match winning run for the first time since February 2025.