Theo Walcott's Arsenal exit regret, snubbing Chelsea and Max Dowman plea

Theo Walcott had two spells with Arsenal's FA Cup opponents Southampton either side of a 12-year spell in North London

When Arsenal take on Southampton in the FA Cup quarter-finals this week, it will be a chance for Theo Walcott to watch two of his former clubs face off. Walcott was one of the most exciting teenagers in English football when he traded St Mary's for the Emirates Stadium in 2006 but still has some regrets about the manner of his Arsenal departure.

The 37-year-old will be taking a watching brief this year, having retired in 2023 after a second Southampton spell. Perhaps fittingly, the final goal of his professional career came against Arsenal, in a 3-3 draw which helped end the Gunners' title hopes.

These days, the role occupied by Walcott in his first Gunners campaign belongs to Max Dowman. At 16, the academy graduate is still a little younger than Walcott was when he made his professional bow but already has two senior starts under his belt.

Even if Dowman spends a full decade playing for Arsenal's first team, he won't have matched Walcott's 12-year spell. The former winger doesn't regret leaving for Everton in January 2018, just shy of 400 senior appearances, though he might have preferred for things to go down a little differently.

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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 his departure. He knew it was time to go, having played just six league games in what would prove to be both his and Arsene Wenger's final season, with the subsequent arrivals of Henrikh Mkhitaryan and Pierre-Emerick Aubameyang only cementing that.

"I had to get my stuff quickly," he 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."

Things could have been very different for Walcott, though, with Arsenal by no means the only club monitoring him at the start of his career. Chelsea looked at bringing him to Stamford Bridge but he decided to stay on the south coast and learn under manager 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."

Like Walcott, Dowman has trusted the process when it comes to a pathway from academy to first team. He was still 15 years old when he made his Premier League debut against Leeds earlier this season and has started in both domestic cups - including Arsenal's fifth-round win against Mansfield.

The youngster has hardly been short of attention, with England manager Thomas Tuchel well aware of his qualities. Dowman has yet to play above Under-19 level for his country but there have been whispers of a World Cup call-up - something which could see him break Walcott's 20-year record as the youngest player to appear for the senior Three Lions side.

Walcott had yet to play for Arsenal when Sven-Goran Eriksson named him in the squad for the 2006 World Cup and handed him his debut in a pre-tournament friendly. It's for this reason that he's not convinced Dowman should head to North America this summer, even if offered a place in Tuchel's selection.

"I hope he doesn't go," Walcott told The Mirror. "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 manager Mikel Arteta will have a decision to make on Dowman - and indeed on some other young players - when he takes his team to St Mary's on Saturday night. When Walcott takes in the action, it may well bring back memories for all manner of reasons.