He was one of Ireland's most enduring and successful broadcasters, but a swindling accountant and a doomed property play during the boom saw Gay Byrne take calamitous hits to the fortune he'd made.
The veteran broadcaster's woes were compounded by punts on bank shares.
He had stuffed money into Anglo Irish Bank, Bank of Ireland and AIB as shares in financial institutions surged before the crash.
Mr Byrne attended an extraordinary general meeting of Anglo Irish Bank at Dublin's Mansion House in January 2009. It was just months before the bank would be nationalised, as the country flirted with economic oblivion.
"A great number of grey haired old crinklies like myself obviously have lost a great deal of money in their pension funds and their shares and they wanted somebody to be held responsible and they got very little consolation from anybody at the meeting," Mr Byrne told the 'Sunday Independent' after the meeting. His son-in-law also worked at the bank.
But he was resigned to the losses he suffered and insisted they weren't enough to overly worry him.
Gay Byrne in the Mansion House before receiving his Freedom of Dublin
"Of course, I've lost money in my pension fund like everybody else [at the meeting] but I've lost money on AIB, Bank of Ireland and everything else as well," he said, "And in the general scheme of things it is very little."
But it was a different story 25 years earlier.
After Gay Byrne's accountant, Russell Murphy, died in 1984, it was discovered that he had embezzled about IR£2m of his clients' money. A number cruncher to some of Ireland's most famous personalities at the time, he is the grandfather of Housing Minister Eoghan Murphy.
Russell Murphy squandered the money - including Gaybo's - in a way that not even his rich clients would have.
Years after Russell Murphy's death, Gay Byrne's daughter Crona said in an interview that her father had lost about IR£160,000 due to the accountant's misdeeds.
Today, that may not seem like such an enormous sum, but bear in mind that trophy homes in Dublin's swankiest areas could be bought for not much more than IR£100,000 back then. A typical four-bedroom home in Dún Laoghaire cost IR£49,000 in 1984.
But Gay Byrne's financial fortitude would be tested again more than a decade later.
He was one of the high-profile investors in a vehicle called the Conduit Partnership, which was assembled by former tax inspector turned property mogul Derek Quinlan.
Mr Byrne had borrowed €1m from Bank of Scotland in 2007 to invest with Quinlan Private.
But with the global economic meltdown that started in 2008, Quinlan Private's investments unravelled.
Last year, Mr Byrne and his family settled a case taken against them by Feniton Property Finance over the €1m loan. Feniton had bought the loan from Bank of Scotland.