'I regret letting Arsenal star complete Chelsea transfer – I even apologised to him'

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Former Arsenal co-owner David Dein has apologised to Ashley Cole regarding the transfer that saw him move to Chelsea under contentious circumstances. Reflecting on events now, Dein acknowledged his regret over the transfer saga and insists it "shouldn't have happened."

Cole was branded "Cashley" by Arsenal supporters following his decision to defect to their London adversaries in 2006. The transfer was tainted by the revelation that Cole had covertly met with then-Chelsea boss Jose Mourinho and other Blues representatives 18 months before his departure.

Mourinho and Cole were both fined over the 'tapping-up incident', while the latter's against, Jonathan Barnett, had his licence suspended for 18 months. Dein, 82, might have persuaded the Gunners hierarchy to provide the funds required to retain Cole, and he featured on the High Performance podcast, voicing his disappointment the academy graduate was permitted to depart.

"The fact that we lost Ashley Cole for a few thousand was crazy," he said. "And to this day, I regret that, and I've apologised to him personally over that, because it shouldn't have happened. But we were so tight for money that everybody was cutting back."

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Dein outlined how Arsenal's cost-reduction strategies were significantly shaped by the development of the Emirates Stadium, which opened in July 2006. But with hindsight, the figures Cole was requesting perhaps shouldn't have proved insurmountable.

The left-back was 25 at the time and just hitting his peak years. He later disclosed in his autobiography that he "nearly swerved off the road" upon discovering Arsenal's best contract renewal offer stood at £55,000 a week, while Chelsea were putting £90,000 a week on the table.

The outcome saw Cole depart for what could now be regarded as a bargain, considering his achievements at Stamford Bridge. Arsenal had been seeking £25million for their player, yet Chelsea ultimately handed over just £5m, with French defender William Gallas heading in the opposite direction.

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"The whole thing went wrong because Arsene [Wenger] and I both thought that what his agent was asking...there was a deal to be done," Dein continued. "We could have cracked it.

"We went to the board and said, 'Look, we're going to have to push the boat out a little bit. And in the end, the board said we can't afford it. And Arsene and I both had to tell him it wasn't going to work.

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"Then all hell broke loose after that, because he had the secret meeting [with Chelsea], as you know. But it was all unfortunate; we shouldn't have lost him. He was an Arsenal boy!"

From Chelsea's standpoint, the transfer proved extraordinarily shrewd. The Blues secured one of the most celebrated left-backs in footballing history for a remarkably modest fee while simultaneously getting under the skin of a fierce rival.

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Cole had already clinched two Premier League titles and three FA Cups during his time at Arsenal, yet it was in west London where he truly made his mark. During an eight-year stint at Chelsea, he added another league title, four further FA Cups, the Champions League and the Europa League to his haul.