Tottenham Hotspur have long struggled with the painful reality of losing some of their biggest stars just as they reach their peak. Whether due to the club’s inability to compete financially with Europe’s elite or a lack of ambition in assembling title-winning squads, Spurs have often been forced to part ways with their best players.
One of the most high-profile departures in recent years was Harry Kane’s move to Bayern Munich in the summer of 2023. Having spent nearly two decades at Tottenham, Kane left in search of the first major trophy of his career. Before him, Gareth Bale made a blockbuster switch to Real Madrid in 2013 after dazzling in North London, while Luka Modric also traded Spurs for the Spanish giants, going on to win multiple Champions League titles.
Interestingly, some players who left Tottenham at their peak have eventually found their way back to the club. Bale returned on loan from Real Madrid in 2020, while recent reports have even linked Kane with a potential comeback. Another notable example is Teddy Sheringham, whose career followed a similar trajectory. After initially leaving Spurs in frustration, he later made his return to the club, proving that some players’ bonds with Tottenham run deeper than a single transfer.
Teddy Sheringham’s First Departure from Tottenham
Sheringham’s initial spell at White Hart Lane came to an abrupt end, and as he recently discussed on the Off The Shelf podcast, his decision to leave was largely influenced by the club’s lack of ambition. The turning point for him came when Tottenham sold Jurgen Klinsmann after just one season, a move that left Sheringham frustrated with the club’s direction.
Reflecting on that period, Sheringham recalled his heated exchange with the club’s chairman at the time. He was desperate for Tottenham to build a competitive squad around him, bringing in world-class talent to challenge for silverware. However, once Klinsmann departed, Sheringham realized that Spurs were unwilling to match his ambitions.
“I wanted the best players in the world to come and play with me at Tottenham,” Sheringham explained. “Klinsmann came here, [Gheorghe] Popescu, we had Darren [Anderton], Nicky Barmby was on the scene. They were top players, and I wanted to be part of a team filled with that kind of talent.”
However, when Tottenham chose not to replace Klinsmann with another marquee signing, Sheringham felt the club had lost its drive. “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, in no uncertain terms, ‘Well, go on then.’”
With that, Sheringham made the difficult decision to leave. Fortunately for him, Manchester United came calling, offering him the chance to join one of the most dominant teams in English football.
Sheringham’s Glory Years at Manchester United
Sheringham’s move to Manchester United in 1997 proved to be one of the best decisions of his career. While he was already a top-class striker at Spurs, his time at Old Trafford elevated him to legendary status.
Competing for a place in the starting XI alongside elite forwards such as Andy Cole, Dwight Yorke, and Ole Gunnar Solskjaer, Sheringham had to fight for his opportunities. However, even when he wasn’t a guaranteed starter, he delivered in crucial moments.
His most iconic contribution came in the 1999 Champions League final against Bayern Munich. Sheringham scored the dramatic equalizer in stoppage time before setting up Solskjaer’s famous winner, securing United’s historic treble. In his four years at Old Trafford, Sheringham won three Premier League titles, the FA Cup, and the Champions League, cementing his place in football history.
Returning to Tottenham
After achieving everything he had set out to win at United, Sheringham returned to Tottenham in 2001 at the age of 35. Despite being in the twilight of his career, he proved he still had plenty to offer, scoring double-digit league goals in both of his seasons back at Spurs.
Even though he left Tottenham once again in 2003, Sheringham remains a beloved figure at the club. His career epitomized the struggles many top players have faced at Spurs—forced to leave in search of silverware, yet always retaining a connection with the club that first made them stars.
Sheringham’s story mirrors that of other Tottenham greats who left in their prime, only to be drawn back by their love for the club. Whether Kane or others follow in his footsteps remains to be seen, but history suggests that for some players, Tottenham will always feel like home.
“Initially, I didnt want to leave’’- Teddy Sheringham says he decided to leave Tottenham because £2m player was sold
