The world for Arsenal has changed in the intervening nine years and yet, like so many child prodigies, it can be hard to imagine Walcott as anything other than the 16-year-old boy who was deemed too young even to attend the press conference to announce his arrival from Southampton.
He is only 26, although in football years it feels like Walcott has had an entire career already, ripe to regale his younger team-mates with tales of a bygone era when a footballer with a tattoo was considered edgy, the only person who took pictures in the dressing room was the club photographer and an England international had to be alive 24-7 to the perils of being merked by Rio Ferdinand.
For Walcott, however, the eternal boy-man of English football, a decision looms on the horizon over his future with Arsenal and on Sunday, when he started on the bench, it looked again like he is slipping further from his manager Arsène Wenger's thoughts. Against Chelsea, it was not until the 84th minute that Wenger eventually elected to send on Walcott, although that is nothing new.
There was the same reluctance from Wenger to use his winger until relatively late when goals were required against both Monaco in the second leg of the Champions League tie and Reading in the FA Cup semi-final. Walcott has started just three league games since his full return from that career-interrupting cruciate ligament injury against Tottenham Hotspur in January last year and its consequences.
With one further season left on Walcott's contract after the summer, it begs the question whether contract politics are coming into play again.
Is Wenger simply unwilling to make changes to a team that has won 24 games in 30 or does his coolness over Walcott have its roots in what he perceives as a reluctance from the player to commit, with no negotiations over a new deal having started yet?
And, in turn, what effect will that have on Walcott's confidence, as he decides where to spend what should be the best years of his career?
What is certain is that neither side has forgotten the last contract negotiations, which reached deadlock in the summer of 2012.
It took Walcott's best-ever season in 2012-13, with 21 goals, to force the hand of Wenger, who had frozen him out in the early part of the campaign. In the end, Walcott made himself undroppable and in January 2013 the club backed down and gave him the £100 000-a-week deal he had sought. He started the next season as a regular, if less prolific goalscorer, and then came that injury.
Walcott is fond of Arsenal, where he has spent more than a third of his life, but you wonder if the club ever forgave him for winning the battle last time.
He was not an academy boy at the club, but he joined so young he can be perceived that way and football clubs often resent paying top whack to their own. As the games run out this season, and with a pivotal summer ahead, Walcott has to ask himself whether he can afford to wait for the weather to change.
Arsenal have developed a healthier competition for places than they had pre-January 2014 but, at 26, Walcott is unlikely to settle for a place as an impact substitute behind an out-of-position Aaron Ramsey or being picked behind Danny Welbeck.
If he is being punished for taking his time over signing a contract in January 2013, he might wish to point out that, in the interim, Wenger himself left it a matter of days before the expiration of his previous deal before he re-signed last May.
But if that relationship has been damaged for good and Walcott is to remain at Arsenal to come off the bench rather than starting games like the one on Sunday, he will know that his future is better served playing elsewhere.
No player leaves a club like Arsenal lightly, but then it is also about knowing when a change of scene will benefit him.
His marginalisation with his club would have an effect on his career for England, where a new generation of Raheem Sterling, Ross Barkley and Harry Kane has emerged, not to mention Walcott's injured Arsenal team-mate Alex Oxlade-Chamberlain - and there are more coming.
These should be the best days for Walcott with England, when seniority and experience kick-in, but there has been little straightforward about his international career encompassing three World Cup finals at which, for various reasons, he has not played a single game.
Another season at Arsenal after this will see Walcott break 10 years at the club and, with Abou Diaby's departure this summer, he will be the longest-serving player in the squad. He is young enough to be an attractive prospect to Liverpool if they were to lose Sterling or to Manchester City and their depleted reserves of home-grown players, in a summer when they are expected to rebuild. The question for Walcott is what he wants from what should be the best days of his life as a professional footballer.
His strength has been the attitude shown in times of adversity. The philosophical response to that 2010 World Cup England squad omission; the quiet confidence in the face of some studs-up criticism from the ranks of the ex-pros; even the 2-0 scoreline on his fingers in January 2014 as he was ferried in stately fashion past the Spurs supporters. A cheerful boy, grateful for the good life conferred on him by playing in English football's days of plenty.
The lowest points of the last 15 months - another lost World Cup finals, missing out on the first Arsenal trophy of his career - have been beyond his control. At his age Wayne Rooney already had 73 caps for England to Walcott's 38. But 10 years into his career, at the age of 26, Walcott is embarking on the second half with a chance to seize back control of his destiny. It might take a brave decision this summer to do so.– The Independent
Original source: Time for Walcott to leave Arsenal?