He revealed he’s lost four friends this year – singers Sinéad O’Connor, Christy Dignam, Tony Bennett and artist Graham Knuttel.
He says a beautiful portrait of Sinéad by talented portrait painter Maureen Roe – which was gifted to him by Cork businessman Michael Mulcahy – will take pride of place in the living room of his home, which already houses two signed pieces of memorabilia Sinéad gave him.
Gerald was one of Sinéad’s solicitors down through the years, and the singer also performed at a number of charity concerts in the ballroom of his Co Wicklow home, Drayton Manor.
“Sinéad played here many times,” says Gerald (65). “She supported The Stunning, she played with Aslan. She was lead with the Hothouse Flowers.
“I think she played about three or four concerts. She was down here many times, stayed over and we’d have a chat.”
Sinéad also sang at Gerald’s ex fiancée Lisa Murphy’s 40th birthday party in 2012.
“My vivid memory of her was sitting on the couch with a dressing gown that was too big for her and a slice of toast,” he recalls.
“She was taking bits of the toast that you wouldn’t feed to a robin. I said to her ‘do you even feel that going into you, would you not take a bite or something?’ and she’d laugh.”
Over the years, Gerald dealt with Sinéad both professionally and personally.
“She had about 12 or 13 lawyers that I know of, including myself,” he explains.
“But we always remained very close friends and she would always come to me with problems. Even up until last year, she would have rang me about two or three personal issues, which I advised her on. Our relationship was very strong.”
“I always saw Sinéad like a sister, a younger sister, I hasten to add. I felt if I could help and protect her in any way I would, and a number of times I did.
“John Reynolds [Sinéad’s first ex-husband] was very good as well. I used to ring him a number of times and he was very good in giving advice.”
Gerald was on a trip to Romania when he heard of Sinéad’s untimely death, and could not make her funeral as he was out of the country.
“I was shocked,” he admits. “Death is strange. I was shocked when Christy [Dignam] passed, yet in 2013 I was in a hospital room in Dublin visiting him and being told by consultants that he only had a few days to live and I remember coming out having spoken to Kathryn, Darren and Kiera and saying ‘I can’t believe it’.
“Yet he lived for so much longer – but when he did die it was a shock. Sinéad was a real shock to me as well.
“She was a beautiful person, and Christy was a beautiful person. I was delighted to see them being honoured the way they were. These are all good people. I’ve always surrounded myself with good people. They’re straight and they’re easy.
“I was in Gozo in Malta when I heard about Christy. Christy and I were inseparable for 35 years, even during the difficult times.”
“I’ve lost four great people in recent weeks, including Sinéad and Christy,” he sighs.
“Tony Bennett wasn’t a big shock, he was in his nineties. Tony came down here and did two concert dinners for me. That was about 10 years ago. We went to the Unicorn restaurant as well.
“Graham Knuttel was ill, he was a really good friend of mine. He was one of the most gifted artists. I’m a big collector and a big fan. I hosted several dinners for him down here. You just never know. Sure I could keel over later, so you have to live for the moment.”
Gerald reckons the 14 concerts at his mansion have raised over €700,000 for various charities.
“The ballroom here holds about 1,600 standing, but we are restricted because of fire regulations, toilets and parking – 800 is the kind of normal,” he says.
“The biggest one recently was Kodaline, with Steve Garrigan. That was a huge one, with 700 people here. They were looking for tickets.
“The proceeds for that concert went to Christy Dignam, and Cork Constitution Rugby Club for the development of young kids, and Down Syndrome. I’ve another one being lined up, which I still have to announce.
“The Stunning, Hothouse Flowers, Mundy, Simon Le Bon. They know it’s all going to charity. These people gave up their time. So many of them were so good to me. They did it all free of charge.”
Gerald also saw an online charity petition he co-headed raise €2.5 million for Barretstown children’s foundation.
He refutes untrue rumours that he had been having money problems after he put his house up for sale.
“I wanted to get a feel for the market,” he says about the initial house sale posting. At first there wasn’t too much interest, but the second time round there was a lot of interest. But I wasn’t that interested in selling and I’m still not.
“People would think I was having bad days, like when the sheriff was moving me out of the office. I was overholding. I was moving into another building and I was there for a year longer than I should have been. I act for the guards a lot of the time.
“I love my work. We’re very busy. We have extended. I’ve three offices, Wicklow, Lucan, Dublin, it’s very busy. And I love it. But I do live today as the last day.
“I don’t know where all this comes from. When I bought a castle and a private jet for Clodagh [his ex-wife] 25 years ago, they said ‘he must be into drugs and guns’ — like I’ve never even smoked a joint in my life.
“When I was done for drunk driving 20 years ago it was on the front pages of the newspapers, that doesn’t bother me, that’s the truth.
“I’m in the top five pc income tax payers in the country. I pay a huge tax bill every year. You would be shattered if you knew the tax I pay.”
After splitting from wife Clodagh Hopkins, Gerald’s next most high profile relationship was with former model Lisa Murphy.
He had been dating Swedish beauty Sonya Valadi in recent years but that relationship ended.
“I dated two lovely blondes after that and now I’m with this lovely Brazilian lady, Andrea,” he smiles. “I met her in the polo club in Wicklow at a party. I’m very much in love with this beautiful lady.
“I party every night, I haven’t changed a bit. I think some people think I might have gone quiet, I haven’t.”
His only child, Kristen, is back living in Ireland after spending a few years in Florida.
“She’s studying for the bar now. She has got a Masters and done a thesis. She is wonderful.”