Theo Walcott’s Arsenal regret, Max Dowman advice and Chelsea rejection – ‘a lot to take’

Theo Walcott has already offered advice to Max Dowman and opened up on his own decisions as a teenager

When Arsenal face Southampton in the FA Cup quarter-finals this week, it will provide Theo Walcott with the opportunity to see two of his old clubs go head-to-head. Walcott was among the most thrilling young talents in English football when he swapped St Mary’s for the Emirates Stadium in 2006, yet still harbours regrets about how his Arsenal exit unfolded more than a decade later.

The 37-year-old hung up his boots in 2023, having returned to Southampton for a second stint at the end of his career. His final professional goal came against Arsenal, in a 3-3 draw which contributed to ending the Gunners’ title aspirations, though it wasn’t enough to keep Southampton in the top-flight.

Today, Arsenal have another exciting teenage talent on their hands in the form of Max Dowman. At 16, the academy product is marginally younger than Walcott was when he made his professional debut but has already started twice this term and scored his first Premier League goal in March.

Even if Dowman remains in Arsenal’s first team for an entire decade, he won’t have equalled Walcott’s 12-year tenure. The former wide man holds no regrets about the actual decision to leave for Everton in January 2018 but rather over how circumstances unfolded when the time came to make the move.

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“When I left I wouldn’t have liked to have gone at night and picked up all the stuff on my own, but that is how it is,” Walcott said after moving to Merseyside.

He recognised the moment was right to move on, having barely featured in the first half of the season. Ultimately, Arsenal added Henrikh Mkhitaryan and Pierre-Emerick Aubameyang in the fortnight after his departure in a double swoop which would likely have only diminished his opportunities further.

“I had to get my stuff quickly,” the winger added. “There was a sense of people being surprised at how quickly it happened and I had to go at night, it was quiet there – there were just a couple of security guards around.

“All I had to put my boots in were some bin bags… it wasn’t the way I would have wanted to have left, but knowing it wasn’t official yet, that no one knew about it, and I had a long way to travel, I had to find time to go in.”

More than a decade earlier, Arsenal were far from the only club keeping tabs on Walcott’s progress at Southampton. Chelsea explored bringing him to Stamford Bridge but he opted to remain on the south coast and develop under boss Harry Redknapp.

“Every time I think of your Dad I smile,” Walcott told Redknapp’s son Jamie in 2020 after rejoining the Saints on loan from Everton. “Before joining Southampton’s academy, Chelsea showed an interest in signing me. But they scared the s*** out of me, to be honest!

“They showed me the first team, the dressing room. I’m seeing Gianfranco Zola, all these guys. That was a lot to take.

“Southampton just showed me the academy side. They didn’t show me anything to do with the first team. You don’t need to be overwhelmed or distracted. That’s why I went to Southampton. It felt right, like a family club. Chelsea was too much to handle at that age.”

Much like Walcott, Dowman has decided the place where he played academy football also represents the best surroundings for a senior debut. He was still just 15 when he made his Premier League bow against Leeds earlier this campaign and has featured from the start in both domestic cup competitions – including Arsenal’s fifth-round victory over Mansfield.

England boss Thomas Tuchel is among those to make it clear he’s aware of what the youngster can do against far more experienced opponents. Dowman hasn’t yet represented his country at senior level but speculation surrounds a potential World Cup selection – which could see him shatter Walcott’s two-decade record as the youngest player to feature for the senior England team.

Walcott was still yet to make his Arsenal bow when Sven-Goran Eriksson included him in the squad for the 2006 World Cup and gave him his debut in a warm-up friendly. Dowman has a little more top-level experience than that but Walcott isn’t convinced it would be right for the teenager to travel to North America this summer, even if Tuchel extends an invitation.

“I hope he doesn’t go,” Walcott exclusively told Mirror Football in March. “I don’t mean it in a horrible way because if I could go back in time, I would change things. I would say to myself: ‘No, no, don’t do it’ but then try telling that to a 17-year-old!

“I do still see him and me differently as he’s playing in the Premier League but he needs to grow at his own pace, especially on the emotional side because he’s a young adult. I had to grow up very fast but this team is still young and not as experienced. He’s being protected, which is important, whereas I had to get thrown in to talk to you lot!

“In time he will go, yes, but I don’t think this is the time and I think there are better players who arguably deserve to be there ahead of him. He will eventually get there but England have wide players doing really well, there’s Bukayo [Saka], [Noni] Madueke, Jarrod Bowen and Anthony Gordon and Harvey Barnes on the other side.”

Arsenal boss Mikel Arteta faces a selection dilemma over Dowman — and indeed several other young talents — when his side travel to St Mary’s on Saturday evening. For Walcott watching on, it could well stir up a host of memories for plenty of reasons.