Arsenal legend Arsene Wenger did plenty to help elevate the Gunners to the top, with lots of shrewd transfer business conducted over his two decades at the club.
The Frenchman was known for his ability to sign stars who may have been somewhat unknown, turning them into first-team gems.
In that time at Arsenal, the north London outfit went on to win Premier League titles and FA Cups, while a final defeat in the Champions League had them so close to European glory.
Arsene Wenger’s success didn’t come without some misses in the market, though, such as Arsenal missing out on Ousmane Dembele.
Before then, there was another move that seemingly haunted the Arsenal boss, which has since been revealed.
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Jermaine Jenas reveals Arsene Wenger transfer conversation as Arsenal regret explained
One transfer miss that came for Wenger in the early 2000s was Jermaine Jenas, a young midfielder who was heavily linked with Arsenal.
While plenty of interest was shown, particularly as a replacement for Arsenal legend Patrick Vieira, a transfer never came about.
In the years that followed, Jenas went on to join North London rivals Tottenham, enjoying a spell there before retiring.
Now, all those years later, the 42-year-old has revealed a conversation he had with Wenger about that transfer that never was.
Speaking on the Filthy Fellas podcast, he said: “I did some work with FIFA a couple of years ago hosting The Best awards and Arsene Wenger works at FIFA now, so I was like ‘I’m just going to ask him’.
“So I was like ‘Arsene, why didn’t you buy me? What happened?’ and he went ‘I know, I knew you were going to ask me this.’
“And he said, ‘Look, I should’ve bought you when you were at [Nottingham] Forest’, he said ‘That was my mistake’.
“He said, ‘When you were at Forest and you were leaving, that’s when I should’ve bought you,’ and obviously he said by then, things have evolved,”
In the end, a move never went through for Jenas, with the rise of Cesc Fabregas helping to build up the midfield ranks at Arsenal.
It’s unclear just how well a move would’ve worked out, but his eventual switch to Tottenham put him on the other side of the North London divide.

Jermaine Jenas’s record against Arsenal
Jermaine Jenas’s career saw him play for clubs such as Nottingham Forest, Newcastle, Aston Villa, Tottenham and QPR before calling time on his career.
While the midfielder never played for Arsenal, though seemingly came close to doing so, he did face them more than any other team.
His record doesn’t make for pretty reading, having won just twice against the Gunners out of 20 meetings with the side.
| Appearances | Wins | Draws | Defeats |
|---|---|---|---|
| 20 | 2 | 7 | 11 |
That could’ve been different, had he played for Arsenal, but instead it’s a team he struggled to play against.
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