David Dein offered the sports entrepreneur Stan Kroenke the chance to buy a portion of his 14.6% stake in Arsenal before finalising a deal with the Uzbek billionaire Alisher Usmanov, but the American declined because he was unwilling to accept Dein's insistence on retaining an interest in the shareholding.
Kroenke, who owns 12.19% of the club through his company Kroenke Sports Enterprises, is understood to have declined the opportunity to more than double his stake because of Dein's proposed ownership structure.
Bankers acting on Dein's behalf have been seeking a buyer for the former Arsenal vice-chairman's stake for some time and are understood to have contacted Kroenke as recently as last week to see if a deal could be done.
Usmanov was understood to be one of a number of potential buyers and on Thursday Dein revealed that he had sold his shares in the club for £75m to the oligarch and his business partner, the London-based fund manager Farhad Moshiri.
It is thought the pair were interested only in buying Dein's entire holding but were willing to retain him as chairman of their investment vehicle, Red & White Holdings.
Dein believes that only by attracting significant outside investment can Arsenal challenge Chelsea, Manchester United and Liverpool for the Premier League title, a premise the managing director, Keith Edelman, has rejected.
The structure of the Red & White deal allows Dein to keep alive his hope of returning to the Arsenal board, from which he was ousted in April after Kroenke's purchase of a significant shareholding in the club. The board believed Dein had undermined its position by approaching Kroenke for investment, although it is now thought that Dein initially made contact with the intention of selling his shares to Kroenke.
In the medium term, however, Dein's influence has surely been diluted. Had he retained his shares his clout would be undeniable, but without them he may be expendable to the billionaire steel tycoon from Russia.
Usmanov yesterday hinted that he would increase his holding in Arsenal. In an interview with the Russian business daily Kommersant, which he owns, he described himself as a passionate Gunners fan. He said he had bought shares in the club not for "strategic" or "political reasons" but as a "portfolio investment". "Arsenal's value has been underestimated," he said.
He said nothing about teaming up with Kroenke to mount a takeover bid proper, a possibility which would probably dismay the current board. But he said he would be interested in "gradually" increasing his stake.