One shouldn’t mess — litigiously speaking — with Parker Rudderham. The Cape Breton businessman who owns Frank Magazine  — a publication with its own storied courtroom history — sometimes seems as (in)famous for his legal battles as his business successes and philanthropic donations.

On October 30, 2012, to cite but one recent example, his hometown newspaper, the Cape Breton Post, scored a two-for-one story that began: “A prominent Cape Breton businessman’s company pleaded guilty to tax evasion Tuesday, the same day he was issued a ticket for his involvement in a fatal motor-vehicle accident.”

The Canada Revenue Agency claimed Rudderham’s Montreal-based Professional Pharmacy Wholesale Service had “voluntarily violated” tax laws by claiming over $1 million in false expenses. Rudderham pleaded guilty in court but not guilty in the court of public opinion, stressing to a reporter he’d have fought the accusation if he hadn’t been in the middle of selling the company.

Although Rudderham was tight-lipped that day about the motorcycle accident — he had been fined $399.91 under the Motor Vehicle Act for failing to drive in a “careful and prudent manner” — he later announced he’d fight the charge. The widow of the motorcyclist then filed suit against him.

And so it goes. Without pretending to be exhaustive, some cases from Rudderham’s docket: In 2003, he was sued by his ex-employer for allegedly violating his employment contract. In 2007, he sued “an ex-wife’s family member for defamation.” In 2011, he threatened to sue the Halifax Herald over its coverage of firings at Frank. In 2013, Frank reported Rudderham sued his second cousin over a $27,000 debt.

All of which by way of saying it is with some trepidation one questions Parker Rudderham.

Still, I was intrigued by his latest legal to-and-fro. Rudderham is suing a Cape Breton woman and son for alleged “cyberbullying” tweets about him. The defendants dispute that and counter the province’s Cyber Safety Act violates Canada’s Charter of Rights and Freedoms.

It’s not the first time a prominent, well-connected individual has invoked our new cyberbullying law against those they claim have criticized them. Is that really who the law was intended to protect? Will the law — and its good intentions — survive a Charter challenge?

No offence intended, Mr. Rudderham.

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