June 13, 2014: “Robotic, predictable and a bit too calculated.” Those were the words chosen by a tearful David Bentley, aged 29 at the time, to describe his views on the modern game while simultaneously announcing his retirement as a professional footballer. Still in his late-20s, Bentley could have continued to ply away with the hope of one day returning to the Premier League, the same league he spent the majority of his career in, the same league that had made him one of England’s brightest prospects a decade earlier, but in the end he decided to walk away from the game. For good.

Ironically, Bentley’s early football career was a seamless journey, compared to the rejections and hardships a lot of players go through to make the top-level, The Englishman’s exceptional talent allowed him to avoid such struggles. Joining Arsenal as a 13-year-old striker, he was training with the senior squad by the age of 16, having now been converted into a right-winger. By the time he was 18, he had made his first senior appearance for the Gunners in January 2003. The main problem, however, was the fact that Bentley’s attempts to break into the first team coincided with Arsenal having arguably the greatest squad in their entire club history in the form of the ‘Invincibles’.

While Thierry Henry, Patrick Vieira, Dennis Bergkamp and co. were mesmerising fans around the world, Bentley found his opportunities limited, and was sent on loan to Premier League newcomers Norwich City for the 2004-05 season. The season at Norwich was largely a success; despite being injured for four months, he managed to play 26 league games for the Canaries and captured a lot of attention in a side that was ultimately relegated at the end of that season.

Not everything was bright for Bentley during this period of his life. Whilst roaming free on the pitch as a mercurial winger, he was trapped by a gambling addiction that had begun when he was a teenager at Arsenal: “I was 14 when I first started going to a betting shop. I got carried away with it,” he would say in an interview later on in his career. “As I started earning more money I really started getting heavily into it. You just get addicted. I was on everything, the horses, the dogs, online with poker, betting on bingo, all sorts … I’d wake up in the morning and the first thing I thought was to have a bet.” Bentley said he would make 50-100 bets a day during the height of his addiction, yet intervention from his girlfriend meant he overcame the problem in 2005 after ending the season with Norwich.

Returning to Arsenal in the summer of 2005, still aged just 20, Bentley decided to hand in a transfer request. His spell at Norwich had given him the irresistible taste of playing regular Premier League football and he wasn’t prepared to stay at Arsenal and warm the bench. Arsenal, however, were aware that Bentley was a potential world-class performer, and did not want to lose him permanently, so a loan deal was agreed with Blackburn Rovers – managed by Mark Hughes. Bentley packed his bags once again, this time to begin the greatest spell he would have in football.

Rovers had escaped relegation in their previous two campaigns, but Mark Hughes, in his first full season managing the club, wanted to change that. Bentley was signed to compliment a pacey, attacking, line-up which also included Craig Bellamy and Morten Gamst Pedersen. By January 2006, Blackburn were riding high in eighth, their highest position under Hughes, and Bentley was a key component to the side. His only visible weakness was a lack of goals: he had only scored one for the club (in a league cup game) since joining in August 2005. Nevertheless, Hughes signed Bentley on a permanent deal for £1 million in January 2006, and was immediately repaid by the player in spectacular fashion.

On 1 February 2006, Bentley became the first player in Premier League history to score a hat-trick against Manchester United as Blackburn earned a stunning 4-3 victory over the side. Bentley continually made a mockery of defender Wes Brown throughout the game. After the match, Hughes, in what, at the time, sounded like the greatest understatement of all time, went on to declare, “I think we have got a bargain in David Bentley.”

Blackburn finished sixth in the league that season, only four points off a Champions League spot, and Bentley had established himself as one of the country’s great young talents. The following season, Blackburn featured in the UEFA Cup and Bentley made his mark on the European stage, scoring an outstanding volley against Austrian side FC Salzburg and also a last-minute winner against Polish side Wisła Kraków, as Blackburn made it to the last-32.

Despite strengthening by signing Porto striker Benni McCarthy, who scored 24 goals during the season, and powerhouse defender Christopher Samba, Blackburn finished a disappointing 10th in 2007, and there was a feeling that it was time for Bentley to move on to a ‘bigger’ club. Yet with interest from Manchester United gathering pace, Bentley committed his future to Blackburn by signing a contract extension, an act of loyalty to the club that had turned him into a star.

The 2007-08 season, his last at Blackburn, saw Bentley continue his consistency, registering 13 assists and scoring eight goals in the league as Blackburn finished seventh. His performances had been rewarded with a call-up to the England senior squad where he made his debut against Israel in September 2007, three months after controversially pulling out the European under-21 Championships due to “fatigue”. Bentley’s decision to pull out had stirred emotions, not least with under-21 manager Stuart Pearce who said “when your country comes calling, you put them first and yourself second”.

Bentley defended his decision, citing: “I’ve never come off a 60-game season and then gone straight into another one, I was alien to it. It wasn’t a rash decision, I asked senior players at England ‘what do you feel like come October or November?’ They said you hit a brick wall.” Nevertheless, despite being a decision made with the idea of prolonging his club career, the media leapt onto the story, using it as a tale of the misguided modern footballer with no passion for the game. Upon making his senior debut for England, Bentley was booed by large sections of the crowd, a first for an England player making his debut.

Back at Blackburn, Mark Hughes, a mentor to young Bentley, left the club at the end of the season to join newly-rich Manchester City, and this essentially convinced Bentley he now needed to make the move to a more successful side. That side was to be Tottenham Hotspur, who paid £15 million for Bentley in the summer of 2008 on a six-year contract.

Bentley was signed by Spurs to be the player who took the team from perennial under-achievers to the Promised Land of Champions League football. He was described by England boss Steve McClaren as the “new David Beckham” and Spurs considered his signing to be a massive coup for the club, having fended off numerous others for his signature. Things, however, did not get off to the greatest start; Tottenham begun the season languishing at the bottom of the table, earning a meagre two points from their opening eight games, and manager Juande Ramos, who won the League Cup with Spurs the previous season but never really settled into the English game, was sacked.

Harry Redknapp took over and his second game in charge, on a cold October night at the Emirates Stadium, proved to be the setting for a game where Bentley would steal the headlines.

Tottenham versus Arsenal is a derby that fires up every player taking part, yet for Bentley, who was essentially deemed not good enough for Arsenal, this game had an added incentive. At 0-0 Bentley received a headed pass from Tom Huddlestone, took it with his chest, and with all the calmness in the world, volleyed it from 40 yards out over the head of Arsenal goalkeeper Manuel Almunia and into the net. It was undeniable quality. The game finished 4-4 and is remembered as one of the league’s finest. For Bentley it provided personal vindication, and also what many assumed to be the start of a fruitful career at Spurs. Sadly, Bentley struggled to make the starting line-up under Redknapp – who preferred to use Aaron Lennon on the right-wing – and fell into obscurity, being cast aside from the England set up as well as Spurs.

A run of 15 straight league starts in early 2010 appeared to mark a renewed faith in the player from Redknapp, however that was hindered by an incident captured on live television after Spurs had secured Champions League qualification in May 2010. Redknapp, giving an interview, was soaked with a bucket of ice by three players, including Bentley. Long before ice bucket challenges became popular, you could see the anger etched on Redknapp’s face, a stark contrast to the child-like grin Bentley displayed, which seemingly confirmed the reputation he had as a troublemaker.

“He never said anything to my face about it – he didn’t really ever say much to me at all – but I knew I was always up against it after that. I hardly got another look-in.” Bentley would lament his actions. Such a seemingly harmless incident can mean so much more in the confines of a football dressing room, and it was clear that Redknapp had enough of Bentley, who was loaned out to Birmingham City in January 2011.

Failing to make the first team there, he dropped down a division in the summer of 2011 to join West Ham on loan, playing in the Championship for the first time in his career, but was ruled out for six months due to a knee injury and sent back to rehabilitate at Spurs. His dramatic fall continued as he joined Russian side FC Rostov in September 2012, although this did give him the honour of becoming the first Englishman to feature in the Russian Premier League.

It was unbelievable to think that only four years earlier he was a £15 million signing who had the world at his feet, seen as a long-term England international who would help Spurs qualify for the Champions League. Now playing for a mid-table Russian side, still aged only 28. Bentley made seven appearances for the club before returning to England, where, now desperate, he went back to the club that made him a star: Blackburn.

The success of his previous stint at the Lancashire club could not be replicated and he made five appearances before being released from his Spurs contract, much to the relief of many Spurs fans who could not fathom how he was still being paid £50,000 a week. After a year without finding a club and having only played 42 games in his last four seasons, Bentley went on Sky Sports and announced he was retiring from the game which, after such a glorious start, had been brutal to him in recent years. “I’ve given up football. It’s over a year since I played my last game and I’ve taken the decision to take my life in a different direction. I felt like it was time to call it a day.”

Bentley now co-owns a restaurant in Marbella which he bought as a player, and recently took part in a Gaelic football match for a TV show earlier this year. He has no plans to ever return to the game as a player.

When it comes to David Bentley people will always wonder how he had such a fall from grace. Was it Spurs? Was it personal or behavioural issues? Were the injuries too damaging? Did he have the mental strength to cope at a top-level? These are questions only David Bentley can answer. Perhaps if he had stayed a little longer at Blackburn Rovers he may still be playing at the top-level; it’s impossible to predict. What’s certain is that the David Bentley story is one which shows, despite the perceived glitz and glamour of the Premier League, it can be a place which is brutal for even the toughest of individuals.

By Santokie Nagulendran. Follow @San_Toki_