“DISASTER ALERT! Jermaine Jenas BEGGED £15M Star to AVOID Spurs’ SINKING SHIP – You WON’T BELIEVE What Happened Next!”
Tottenham Hotspur have had their share of disappointing signings over the years.
Tanguy Ndombele struggled to make an impact at Tottenham after a high-profile move from Lyon, and Richarlison has also failed to live up to expectations since his switch from Everton.
Looking back even further, David Bentley stands out as another example of a player who failed to deliver at Spurs despite arriving with plenty of promise.
Bentley was once regarded as one of England’s top young talents.
Tottenham paid £15 million to sign him from Blackburn Rovers, a fee that would equate to around £60 million today, according to Sky Sports’ transfer inflation calculator.
Despite the investment, Bentley never lived up to the hype in North London.
Former Tottenham midfielder Jermaine Jenas recently spoke about Bentley’s ill-fated move on the Filthy Fellas podcast. Jenas revealed that he actually advised Bentley against joining Spurs at the time.
Jenas explained that while he had great respect for Bentley’s talent during his time at Blackburn, he didn’t believe the move to Tottenham was right for him.
“I actually told him not to sign for Tottenham, and I loved him,” Jenas said.
“When he was at Blackburn, he was flying. We were both signed with Puma, so we did events together. On one of those, he told me he was thinking about joining Spurs.”
Jenas tried to talk Bentley out of it. “I told him, ‘Don’t do it.’ He asked why, and I told him straight — ‘You’re not going to play.’ Aaron Lennon was the starting right winger, and Spurs’ style relied heavily on pace and direct play, which didn’t suit Bentley’s strengths.”
According to Jenas, Bentley was confident he could earn a place in the team. “He said, ‘No, no, I’ll get in,’ but I warned him — Lennon wasn’t giving up that spot easily.
Sure enough, Bentley arrived, and Lennon made it clear he wasn’t stepping aside.”
Bentley ignored the advice and joined Spurs in 2009. His time at the club was underwhelming. He made just 62 appearances and never truly established himself in the squad.
One of his most memorable moments came off the pitch — drenching manager Harry Redknapp with a bucket of water in celebration after securing Champions League qualification in 2010.
That moment, more than any performance, seemed to define his time at Tottenham.
After only two full seasons, Bentley moved on, going out on loan to clubs like Birmingham City, West Ham, and even Russian side Rostov.
He eventually returned to Blackburn before retiring from football altogether before turning 30.
In hindsight, Bentley’s career might have unfolded quite differently had he taken Jenas’ advice and steered clear of the move to Spurs.
