I regret letting Arsenal star leave for Chelsea - all hell broke loose and I'm sorry

Ashley Cole's move from Arsenal to Chelsea was framed as a betrayal when it unfolded, but one of the Gunners' decision-makers at the time has described his regret as "all hell broke loose"

Former Arsenal co-owner David Dein has apologised to Ashley Cole over the deal that allowed him to join Chelsea under controversial circumstances. Looking back now, Dein regrets the debacle and says it "shouldn't have happened."

Cole was dubbed "Cashley" by Arsenal fans after jumping ship to join their London rivals in 2006. The move was soured by the fact that Cole had secretly met with then-Chelsea manager Jose Mourinho and other Blues figures more than a year prior to his transfer.

Mourinho and Cole were each fined over the 'tapping-up incident', while the latter's agent, Jonathan Barnett, had his licence suspended for 18 months. Dein, 82, might have convinced the Gunners board to fork out the money needed to keep Cole, and he appeared on the High Performance podcast, expressing his remorse that his homegrown star was allowed to leave.

"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 explained how Arsenal's cost-cutting methods were heavily influenced by the construction of the Emirates Stadium, which opened in July 2006. But with the benefit of hindsight, the numbers Cole was asking for perhaps shouldn't have proved prohibitive.

The left-back was 25 at the time and just coming into his prime years. He later revealed in his autobiography that he "nearly swerved off the road" upon learning Arsenal's top offer for a contract extension was worth £55,000 a week, while Chelsea offered him £90,000 a week.

The end result saw Cole leave for what could now be considered a pittance, given his success at Stamford Bridge. Arsenal wanted £25million for their player, but Chelsea ended up paying just £5m, while French defender William Gallas moved in the opposite direction.

"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.

"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 a Chelsea perspective, the deal was an incredibly valuable one. The Blues got their hands on one of the most respected left-backs in the history of the sport for a very acceptable sum, not to mention riling up a key rival in the process.

Cole had already won two Premier League titles and three FA Cups with Arsenal, but truly cemented his legacy in west London. It was there he won another league crown, four more FA Cups, the Champions League and the Europa League across an eight-year spell.

It serves as a cautionary tale to other clubs as to how sometimes short-term investment can save some pain in the long run. And from his comments, it's evident Dein is all too aware of the lessons he learnt from one of the most bitter transfer sagas in Premier League history.