The signing of David Bentley in the summer of 2008 remains Tottenham’s biggest, with payments of up to £17m for a player who looked vastly over-priced at the time and four years later looks to be an expensive aberration in the otherwise savvy dealings under Daniel Levy’s stewardship.
Despite previous loans spells away from White Hart Lane to Birmingham City and West Ham United, Bentley remains on the Tottenham payroll, an expensive legacy of ex-Director of Football, Damien Comolli’s, judgement. However, after four largely fruitless years, Bentley now has another chance to shine, with new Spurs Head Coach Andre Villas-Boas prepared to give everyone a fresh start.
Bentley’s main highlight for Tottenham so far was a stunning goal in a memorable night at the Emirates that opened the scoring in an eight-goal North London Derby thriller. That goal came not long after he signed in 2008, when he was still being named in the starting XI, but he soon lost his place on the right-side of a four man midfield to the genuine winger and match-winner Aaron Lennon.
When Lennon was injured in the final third of the 2009/10 campaign, Bentley stepped in, notably turning cup games around at White Hart Lane while producing steady performances as Spurs qualified for the Champions League.
While he contributed for Spurs from the right-flank then, a position he played for Blackburn when he was signed, with no discernible pace, he has never been a winger. If Spurs were to adopt a 4-4-2 in the forthcoming season he could play on the right, with the promising prospect of Kyle Walker overlapping him, but he will always be behind the much more talented Lennon in the pecking order.
It is unlikely Villas-Boas will play a 4-4-2, though, so it was interesting to see Bentley playing as the most advanced player in a 4-2-3-1 when the new Head Coach officially named his first team in the friendly at Stevenage this week.
Bentley's best days at Arsenal were arguably when he played in the hole, just behind the main striker, on occasions when he covered for Dennis Bergkamp in games as Arsene Wenger rotated his squad. So, a 4-2-3-1 could well suit him better.
If Villas-Boas goes with a 4-3-3, a position in a three-man central midfield would allow others to compensate for his lack of defensive attributes. Villas-Boas may also like the idea of Bentley playing deeper in a packed midfield, with Bentley’s ability to spread the play and create counter-attacks with what the new coach would call a “vertical” range of passing.
When Villas-Boas took the reins earlier this month he spoke about everyone starting from a clean slate, while Bentley said he was keen to show the new coach what he can do. Assuming he doesn’t take this as invitation to kick a ball into a skip from a great distance, he may get a second chance at Tottenham, long after most of us had considered his transfer fee and wages to be dead money.