Former Spurs striker Teddy Sheringham has recalled the moment he was told Tottenham were trying to pull off one of the most astonishing transfers in football history.
There was once a time when Tottenham Hotspur could genuinely attract some of the biggest names in world football to White Hart Lane. And we are not talking about just any superstar. We are talking about Diego Armando Maradona, arguably the most famous footballer on the planet at the time.
Eight years after Maradona pulled on a Tottenham shirt during Ossie Ardiles’ testimonial against Inter Milan, the Argentine’s close friend had become Spurs manager and attempted to bring him permanently to north London.
The move never materialised, but according to Teddy Sheringham, it came far closer than many supporters may have realised.

Teddy Sheringham lifts the lid on Tottenham’s failed Diego Maradona move
Speaking on talkSPORT, Sheringham revealed that head coach Ardiles approached him in 1994 to ask for his thoughts on signing Maradona, who was nearing the end of his career after a controversial World Cup campaign with Argentina.
“We’re going back a few years, and you’re talking about people you’d want to sit down with. Maradona would have to be one,” Sheringham said.
“Ossie Ardiles was my manager at Tottenham, he came to me one afternoon. He said, ‘I want your opinion on something, Ted. I’m thinking about signing someone, what do you think?’
“I went, ‘Well, go on, who?’ He went, ‘Maradona’.
“I just erupted and was like, ‘Ossie, just do it’. He said, ‘Okay, it’s in the pipeline’.”
“He came back a couple of weeks later and said, ‘Look, we can’t sign him. There’s too much baggage. But we’re going to sign Jurgen Klinsmann instead.’
“Five minutes later, Klinsmann was at the club and all was forgiven. But Maradona would have been a good one.”
Jurgen Klinsmann became Tottenham’s superstar instead
While missing out on Maradona was undoubtedly disappointing, Tottenham supporters did not have to wait long for another global superstar to arrive in north London.
Jurgen Klinsmann completed his move to Spurs in the summer of 1994, with then-chairman Alan Sugar famously helping convince the German to join the club. Despite arriving with a reputation for diving, Klinsmann quickly won over the White Hart Lane faithful with his performances.
His partnership with Sheringham became one of the Premier League’s most entertaining duos, given the pair combined for 38 league goals during the 1994/95 campaign, with Klinsmann scoring 20 in his debut season alone.
Although his first spell lasted just one year before he returned to Germany with Bayern Munich, the forward returned on loan in 1998 and played a crucial role in helping Spurs avoid relegation, most memorably scoring four goals against Wimbledon in a dramatic end-of-season clash.
Across two spells in north London, the German netted 40 goals in 68 appearances and cemented his place as one of the club’s most popular modern-era signings.
