As a fresh-faced young cadet at the Sydney Morning Herald, I was dispatched to do a rotation at the now-defunct Eastern Herald, the Bondi Junction outpost of the Fairfax media operation.

My job was to write a gossip column called "Chums," the very name of which seemed to indicate it would be an innocuous piece of fluff destined to be dispatched, unread, to line our readers' budgie cages.

The tedium of chronicling the Eastern Suburbs cocktail set, populated by shoulder-pad wearing blondes with bouffants who looked like extras from Dynasty, quickly wore thin. Chums needed an antidote.

The mid-week greyhound races at Wentworth Park would do the trick. The clobber of choice was the tracky-dak teamed with ugg boots.

To my surprise, I stumbled upon a largish man in a crumpled suit who wore thick glasses and his black hair swept back in an unfashionable style. Not only did his suit set him apart, but this man seemed to be right on the money in every race.

This phenomenally successful backer of dish-lickers was none other than Labor MP Rex "Buckets" Jackson, the former prisons minister. It came as no surprise when he was subsequently jailed for accepting bribes for arranging the early release of prisoners.

Fresh from the thrill of reporting on Buckets at the dogs, in January 1986 Chums decided to cover a wedding at Kincoppal School in Rose Bay because crime figure George Freeman and his wife Georgina formed part of the bridal party. Their three-year old son Adam, decked out in a miniature white tuxedo, walked down the aisle carrying the wedding rings on a lacy pillow.  

Under the headline, "The bride wore sequins, the bodyguard a tux…." I noted that the bride, Georgina's sister Julie, and her attendants were wearing sequins. I suggested that due to the presence of Freeman, this was "the closest fashion accessory to amour-plating".

We also ran a photo of the underworld figure's bodyguard, a meat-headed lump of a man. The accompanying caption - "I could be so good for you …" - was a play on the hit series Minder, which featured the antics of a small-time English criminal Arthur Daley and his faithful bodyguard Terry.

For some inexplicable reason, George Freeman failed to see the humour in my story. I started receiving threats at my home, with anonymous callers informing me that I had gone too far and that "Mr Freeman was not happy".

After nights of interrupted sleep, my flatmates insisted I call the police. The police organised with the Edgecliff branch of Telecom (Telstra's predecessor) to put a tap on my phone. I never received another call.

Years later I was told that Freeman had been tipped off by his corrupt contacts in Telecom. For years he had allegedly been illegally using their phone lines to run his SP bookmaking outfit.

But rather than put me off, Freeman's threats galvanised me. It sparked a lifelong interest in organised crime. Four years after writing that article, I broke the story of Freeman dying of an asthma attack after a malfunction with the oxygen cylinder he kept in his house.

A postscript to that story is that Adam Freeman, the three-year-old ringbearer at his aunt's wedding almost 30 years ago, is now in jail. He was recently sentenced to five years non parole after pleading guilty to the manufacture of 19 kilograms of ecstasy.

His mother Georgina asked the sentencing judge to take into account that her son had already been punished enough having been bashed on the head with a can of tuna while in jail on remand.

Even better than a gangster's wedding is a funeral. Emotions run high, wives and mistresses clash, guests threaten each other and occasionally journalists, while undercover police take it all in through their long-lensed cameras.

At George Freeman's funeral, the formidable underworld figure Lennie McPherson brusquely waved aside his four minders, all sporting broken noses and bulky frames, to hold an impromptu press conference to honour his mate.

"I think the greatest gift from God is George Freeman for me," said the crime boss, who met Freeman 40 years earlier when they were both in jail.

During the eulogy, it was joked that Freeman's welcome at the Pearly Gates would have been warm and St Peter would have greeted him by saying: "Come on in, mate. God wants to know your tips for the Golden Slipper."

Outside the church, McPherson quipped that "Every tip he ever give me got up."

Freeman's tips were remarkably accurate - 99 per cent, he once boasted. The accuracy might have been enhanced by the fact that Freeman was rigging races.

Six years later, in August 1996, while serving a jail term for the bashing of a rival, McPherson, the nation's "Mr Big" of organised crime, shuffled off his mortal coil.

There were quiet guffaws among we journalists at McPherson's funeral when his daughter Janelle said of her father: "He chose a path in life that you and I might not have chosen but at least he could say he was at the top of his profession."

Just before McPherson was jailed he was embroiled in an ongoing dispute with Australia Post and Hunters Hill Council over his failure to have a street number on his well-fortified Gladesville mansion.

In response to a letter from Australia Post ordering him to put a number on his house, the irate crime boss rang the local post office where he was put on to a hapless postal clerk.

"It's McPherson here, Prince Edward Street."

Clerk: "Yes, I know who you are, Mr McPherson. You would have had a letter about not displaying your house number. Why don't you have one?

McPherson: I took it down.

Clerk: Why did you do that?

McPherson: Because some bloke threw a bomb through my front door."

But still the postal clerk persisted: "There's no point in not having a number," he offered. "One neighbour has 20 and the other has 24.

"Yes, but these criminal types aren't too bright," retorted McPherson. "By the time someone checks on number 20, then checks on number 24, I'll be ready for him."

McPherson never did put that number up.

McPherson was right about criminal types not being too bright. One of his less-than-salubrious friends threatened me outside All Saints Anglican Church in Hunters Hill, as mourners made their way out of his funeral service.

A firm believer in discretion being the better part of valour, I decided not to get to close as McPherson was interred in a vault at the Field of Mars cemetery in Ryde.

As I made myself scarce, standing behind an ostentatious black marble crypt, I overheard the most remarkable conversation. McPherson's dodgy lawyer Con Karageorge was discussing where he had hidden McPherson's money and boasted how the National Crime Authority investigators would never find it.

But within weeks of the funeral Karageorge was arrested and he was later jailed for trying to buy a false passport from an undercover NCA officer.

As we all know, Sydney is a small town. One of my friends reminded me recently that the first time she met me I was hiding behind a hedge at our children's primary school.

I had just spied fellow parent "Big" Jim Byrnes, whose nefarious exploits I had been covering in the paper.

Big Jim was subsequently a "person of interest" at the coronial inquiry into the murder of his associate Max Gibson, who had died of a heroin hotshot during his trial for blowing up a house that Big Jim was in the middle of buying.

Big Jim was not happy that I was covering the inquest and he asked Coroner Jacqueline Milledge if his evidence could be suppressed because "a certain member of the Fairfax press" persisted in writing unflattering articles about him.

The Coroner pointed out she had seen us having lunch the previous day, to which Big Jim replied "but that's because we are parents of the same child."

To my horror counsel assisting Patrick Saidi turned to look at me before saying: "I can see the Telegraph's headline tomorrow: 'Herald journalist has witness' love child'."

What Big Jim meant to say was that we were parents at the same school. In fact, he later tried to rope me into singing a duet with him at the school talent quest.

He suggested we perform Anything You Can Do, I Can Do Better.  By way of enticement he even offered to throw in Roger Rogerson on the piano. I declined.

I also turned down the offer to go to the famous Rolling Stones concert at the Enmore theatre with accused murderer Tom Domican.

In the words of Falstaff in Shakespeare's Henry IV: "The better part of valour is discretion, in the which better part I have sav'd my life."