He built a successful law practice, created a cable television empire, remade a province, launched a successful professional hockey franchise and now he wants to found his own new town on the edge of his St. John’s hometown. Not surprisingly, Danny Williams has learned a few lessons along the way too.

He was 50 years old and… Now what? It was the late summer of 2000, and Danny Williams had flown to Jamaica with a friend to weigh his options.

He had been a lawyer for close to 30 years. He had helped grow his father’s St. John’s law firm into one of the city’s best known and most successful. He was most proud of – liked to brag about – the “street” law he and his partners sometimes practised, including having successfully defended a number of battered women facing murder charges. He’d had a satisfying legal career, but he needed a new and different challenge.

In parallel with his legal practice, Williams had also managed to create (coupling a borrowed $2,500 investment in the early 1970s with a workaholic’s obsessiveness for his whole life) his own cable television empire worth – “count the zeroes” – $250 million. But he’d run out of room to expand those horizons too. He’d recently tried, and failed, to talk the owners of other family-owned cable providers in Atlantic Canada into combining forces to create a publicly-traded regional cable juggernaut that could compete with Bell and Rogers. By the time that scheme failed (“no one wanted to give up control”), Williams had already made the major investments in new digital technology to make his own Cable Atlantic so state of the art, “I’d reached the end of that road too.”

Which is when, and perhaps why, the political fork in his career road beckoned. Again.

During the 1980s when his family was younger, Williams had said no to an entreaty from then-premier Brian Peckford to run in St. John’s East where polls showed he could have won. Later, in the messy middle of the political scandal over the Sprung Greenhouse (a doomed high-tech scheme to grow cucumbers in six days, into which Peckford had invested $13 million of taxpayers’ dollars and much of his own political capital), Williams had quietly approached the premier. “If you’re really in trouble and you need someone to run as an MHA…” But Peckford himself resigned soon after.

Now, in the summer of 2000, the current Tory opposition leader, Ed Byrne, had just announced his own surprise resignation. Williams consulted his wife and now older children again. With varying degrees of enthusiasm, they agreed they would support him this time if he chose to run for leader.

But should he? Would he?

Which was why he’d decided to spend a week in Jamaica with a friend (a long-time Liberal, as it turned out) pondering what to do next. “It was my walk in the sand,” he jokes. They talked, he walked on the beach.

“One morning, I got up, looked in the mirror and I thought, ‘It’s time to shit or get off the pot. It’s time to give back.

Politics, in truth, has coursed through Danny Williams’ veins for as long as he can remember. His father played the political strategist, “a headquarters guy” for both the provincial anti-Smallwood and the federal pro-Diefenbaker Progressive Conservatives; his mother, Teresita, worked in the trenches as the passionate party activist and campaign manager. “One of my earliest memories,” Williams says, “is carrying around signs for (Tory candidates) Jim McGrath, or Bill Marshall, or one of those guys.”

Despite that, Williams insists that while he was growing up he didn’t harbour political ambitions of his own. He was more interested in the law … and success. After graduating from Memorial University at the precocious age of 19 and spending two years studying law in England as a prestigious Rhodes scholar, Williams enrolled at Dalhousie University’s law school in Halifax in the early 1970s, managing to squeeze what should have been an 18-month Canadian LLB qualifying program into one year. By then, he was married to Maureen, his childhood sweetheart, and “eager to get on” with the business of assuming his rightful place in the Newfoundland legal establishment.

Which, fortuitously, was when one of the partners at HR Doane (a then-prominent Halifax accounting firm where Maureen worked as a secretary) approached him with a proposition. The partner was working with a group applying to the CRTC for a cable television licence for a Halifax suburb. Why didn’t Williams put together his own group and apply for a cable television licence in Newfoundland?

“What’s cable television?” Williams asked.