Arsenal have handled plenty of transfers over the years but one five-year contract renewal ended prematurely
David Bentley pictured
David Bentley's Arsenal tenure ended rather abruptly(Image: Getty)
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David Bentley left Arsenal just six months after penning a five-year deal. The midfielder cited a lack of trust in Arsene Wenger, who was the last manager to guide the club to a league title before Mikel Arteta's success last season.
The Gunners have earned major credit following their Premier League title win and some big names are being linked with a move to north London this summer. Arteta has secured Piero Hincapie, Illan Meslier and Christos Tzolis so far.
But one former player who would have enjoyed more time in north London, in hindsight, is Bentley. The Englishman joined the Gunners at 13 and enjoyed his youth career in north London. He signed his first professional deal in 2001 and debuted under Wenger two years later. However, Bentley went out on loan to Norwich City in 2004 and handed in a transfer request upon his return.
He secured a move to Blackburn in January 2006 after impressing on loan and eventually signed for Arsenal's rivals Tottenham for £15million in 2008. But, during an appearance on the Undr The Cosh podcast, Bentley admitted that he should've spent more time with the Gunners but didn't have confidence in Wenger's plans.
David Bentley speaks on a podcast
Bentley spoke out about his time as a Gunner(Image: Undr The Cosh/YouTube)
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He said: "When we were playing, you were under much more pressure than players are nowadays. Much more pressure. Because, if you found yourself out the team, you were criticised more than you are now. Now, you're a squad player. Just having a rest, not in the squad today.
"[I left Arsenal because] I wanted to play. I signed a five-year deal and left after six months! Wenger was like, 'No, do this.' He had a plan, didn't he? But I couldn't see that plan. Didn't trust it.
"Potentially, I could have stayed; I should have stayed. Remember, I saw the young lads come through, Cesc. I made my debut with Fabregas - my full debut.
"Absolutely unbelievable performance from him. We beat Wolves 5-1 at Highbury. He dominated the game at 15 years old. I was only like 17. Eighteen months older, or two years older than him."
After leaving Arsenal, Bentley's time at Blackburn was the peak of his career. The midfielder was named the club's Player of the Year in 2007 as he was linked with a move to Manchester United.
David Bentley playing for Spurs
The Englishman would go on to sign for Spurs(Image: Getty)
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In 2008, he headed to Spurs and his first goal for his new side was arguably his greatest. Bentley fired in a 43-yard volley during a 4-4 draw with his former club Arsenal.
This incredible goal was not indicative of what was to come, as the ex-England international would go on loan four times while at Spurs. He had stints at Birmingham City, West Ham, FC Rostov and a return to Blackburn before retiring at just 29 after being released by Tottenham.