Tottenham Hotspur have a sour history of having to sell some of their best players at the peak of their powers.
Harry Kane left Tottenham last summer to join Bayern Munich in pursuit of the first trophy of his career.
Meanwhile, Gareth Bale left Spurs in his prime to join Real Madrid, as did Luka Modric.
Of course, Gareth Bale would return to Tottenham on loan further down the line, while Harry Kane has been linked with a Tottenham return recently too.
Another player who left Tottenham only to re-join Spurs later in his career was Teddy Sheringham.
Speaking on the Off The Shelf Podcast, Sheringham has been discussing his departure from Tottenham the first time around, and he says that he was driven to leave Spurs after Jurgen Klinsmann was sold.
Why Teddy Sheringham left Tottenham
Sheringham spoke about his departure from Spurs the first time around.
The striker says that he had a real argument with the Tottenham chairman after Jurgen Klinsmann was sold, and that the club’s lack of ambition to bring in top players forced him to go and find a new challenge.
Klinsmann left Tottenham just one year after his £2m move from Monaco.
“I wanted the best players in the world to come and play with me at Tottenham. Klinsmann came here, Popescu, you know, we had Darren, Nicky Barnby was on the scene,” Sheringham said.
“They were top players. I wanted the best players to come and play with me. Once Klinsmann left the first time, it was, that was not going to happen.
“They were, for some reason, Tottenham got their fingers burnt and they were not going to sign the top players that I wanted to play with. In the end, I had a row with the chairman and I just said, look, I want to go and he said, well, go on then, in no uncertain terms, go on, if you want to go. If you can’t tell me that we’re going to be signing these top players again, I don’t want to be here.
“He went, well, go on then, go. It was like, okay. I was lucky enough that Man United came in for me and fitted into a team that was already a machine.”
Teddy Sheringham stats for Manchester United
Sheringham forced his way out of Tottenham to join Manchester United, and while Spurs fans may not agree, that was one of the best decisions Sheringham ever made.
Indeed, while Sheringham was a Tottenham legend in a lot of ways, he cemented his legacy during his time at Manchester United.
The striker wasn’t necessarily always the first name on the teamsheet at Old Trafford as the likes of Andy Cole, Dwight Yorke and Ole Gunnar Solskjaer jostled for position.
However, Sheringham did win numerous honours at United, and he also had some very memorable moments, including a goal in the 1999 Champions League final.
| Games | 156 |
| Goals | 43 |
| Assists | 31 |
| Champions League wins | 1 |
| League titles | 3 |
| Other trophies | 1 |
| PFA Player of the Year awards | 1 |
Sheringham would eventually return to Tottenham in 2001, just after winning the PFA Player of the Year award with United, and even at the age of 35 at the time, Sheringham would hit double figures in terms of league goals in both of his seasons during his second spell at Tottenham.
