I was an Arsenal wonderkid but it didn't work out – I look back with a lot of regrets

Arsenal are back in action in the third round of the Carabao Cup on Tuesday night against Ipswich Town

A number of familiar faces have played for Arsenal and their Tuesday night Carabao Cup opponents Ipswich Town over the years – including Francis Jeffers.

Jeffers, who is now assistant manager of Macclesfield in the National League North, was considered by many as the next big thing when he joined the Gunners from Everton in 2001. Dubbed a "fox in the box" by Arsene Wenger, the Frenchman paid a not inconsiderable fee back then of £8million to bring him to Highbury.

However, the young striker never managed to hit the same heights in north London that his emerging talent promised at Goodison Park. Having scored 20 goals in 77 appearances for the Toffees, he managed just eight goals in 39 games across three seasons with Arsenal, who subsequently loaned him back to Everton in 2003.

In a career disrupted by injuries, including during his time at the Gunners, Jeffers failed to live up to the talents that his initial impressions promised. Discussing his move to Arsenal in 2017, the former striker admitted the career-defining decision was "probably" the wrong one. He said: "I’ve got to be really honest, looking back on my career I left the club too soon.

"[Arsenal] wasn’t the right move for me but it was a difficult time because of the way our Football Club was then, it wasn’t like it is now. It was a good move for me and the Club at the time but it was definitely too soon and probably the wrong move.

"I went from being a regular at Everton to going down there and not being able to get into the team. When you’re sitting at home at think back at how your career’s gone, I feel my head was turned.

"I was only young. It was difficult because I felt Arsenal were the best team in the league at the time. I’d just watched them play Liverpool in the FA Cup final and absolutely battered them but came out losing the game.

"It was a tough decision for me because I’m an Evertonian, I’d been a season ticket holder all my life. It was a big decision but one that never worked out for me."

Despite holding "a lot of regrets" for his time spent in north London, the former striker revealed in 2014 that he still had a lot of respect for his ex-manager Wenger. Speaking to The Independent in 2014, Jeffers said: "I was out partying, living life, tossing it off in training because I always thought I wouldn’t play Saturday anyway.

"Now, I look back with a lot of regrets. That is where I should have been putting it in more. Wenger gave me a fair crack of the whip. I haven’t got a bad word to say about him. He tells you how it is, one of the only managers I played for who did.

"He said there were things going on in my head that shouldn’t have been and that it was an important time in my career. I am not saying I threw it all away, because I had a decent career. I fulfilled a lot of ambitions but I always say it, I know how much ability I had. I’m not soft. I know how good a player I was. One England cap wasn’t enough."

Following a disappointing time at Arsenal, Jeffers had stints at Charlton Athletic, Rangers and Blackburn Rovers before arriving at Ipswich for a month-long loan in 2007. He made seven goal contributions in nine games, leading the club to try and negotiate a permanent move for him.

However, Ipswich couldn't secure Jeffers after three failed bids. Speaking about his time in Suffolk, Jeffers admitted he loved the relationship he built with the fans in such a short time.

After joining Ipswich as a first-team coach in 2021, the 45-year-old said: "I played here many years ago and I've seen some familiar faces around the building which was nice and brought back some good memories.

"I loved my time here, although it was short, and I had a great relationship with the fans. They really took to me and I took to them and now it's great to be back."

After a short time coaching with the Tractor Boys, Jeffers sharpened his coaching skills at the likes of Oldham Athletic and is now the assistant manager of Macclesfield FC.

FOLLOW OUR ARSENAL FB PAGE! Latest Gunners news, analysis and much more via our dedicated Facebook page