Former Leyton Orient owner Barry Hearn says he now regrets selling the club to businessman Francesco Becchetti.
Lifelong fan Hearn sold the club to the Italian for £4m in July 2014.
This week the club was served with a winding-up petition from Revenue & Customs for non-payment of tax, with a High Court hearing set for 20 March.
"Looking where we are now, I would never have sold if I had thought this was going to happen," Hearn said. "Hindsight is a wonderful advisor."
He told BBC Radio 5 live: "At the time I thought it was perfect for everybody - fans, myself, the club."
Hearn, who was Orient chairman for 19 years, said when the takeover was completed, he and fans were "pretty certain" that Becchetti, who made a fortune in waste management and recycling, would prove to be a good owner.
"He had a very engaging personality," the 68-year-old said. "He seemed passionate about what he wanted to do, and he has done what he told me he was going to do - he has injected many, many millions of pounds into Leyton Orient.
"It is just that putting the money in, and spending it wisely are not always the same things."
A meeting of the Leyton Orient Fans' Trust (Loft) on Thursday night agreed on what the group calls "a last-resort measure" to try to save the relegation-threatened club.
Should Becchetti not pay the tax bill before the court date, then at the winding-up hearing the fans would seek the appointment of an administrator, despite the fact it would mean the club being deducted 12 points under English Football League rules.
An administrator would then look to sell the club as a going concern to a potential new owner.
"That application would be made as late as possible to give the club's current owner time to settle the bill," said Loft spokesman Tom Davies.
However, he added that should an adjournment of the court hearing provide a more stable course and future for the club, then they would favour an adjournment.
In addition, Loft has launched a crowd funding page to try to raise £250,000 - reportedly the tax sum owed by the club.
Hearn still owns ground
Loft also want to meet Hearn, still the chairman of World Snooker, to discuss its plans for saving the club.
"I have been a bit critical of fans' trusts in the past up and down the country. Some of them have worked, but some of them have been abysmal failures," he said.
"But I think they should be encouraged and applauded for looking at the situation. It comes down to what plan they have in their mind, what is the sustainability of the club within that plan and what management, because it is all about management."
Hearn still owns Orient's Matchroom Stadium. But for that, he believes it could have been sold for redevelopment.
"Fortunately Leyton Orient have got a 20-year lease on the ground, with another 20-year option. I did it on purpose because I could never be 100% sure where I was selling," he added.
"I kept the ground to make sure it wasn't used for the wrong reasons - that it wasn't the wrong reasons for buying a football club. Thank goodness I kept it because I would imagine now, with the situation it is, developers would be knocking on the door tomorrow."
When asked by BBC Sport, Leyton Orient declined to respond to Hearn's remarks or comment on Loft's proposals.