Book Review: Bootstraps Need Boots: One Tory’s Lonely Fight to End Poverty in Canada

Jamie Swift

What happens when we’re young shapes us for life.

That seems obvious, but it’s worth keeping in mind, particularly when we ponder the stubborn persistence of poverty in one of the world’s richest countries.

Hugh Segal — former senator, longtime professor, lifetime politico — was born in Montreal in 1950, an “edge-of-poverty working class kid,” as he refers to his upbringing in the book.

One frigid winter day in the 1950s, his oft-unemployed cab-driver dad gave young Hugh’s treasured wooden toy box to a neighbour living in the same triplex. The man didn’t have the money to fuel his furnace. Young Hugh resented this act of charity. He would later come to understand that there were people poorer than the Segals.

His family scraped by, navigating setbacks familiar to people living with less. The events seared themselves into his consciousness.

“A bailiff arriving to seize your dad’s car and empty the house of furniture is not something that fades into distant memory. It stays with you, like a dark spot at the edge of a slice of bread,” he reflects.   

What works so well here is this former corporate executive’s visceral understanding of the pathologies of poverty. The way that feelings of insecurity and instability so often mould young lives, generating anger and loss, can “shape attitudes and emotional responses for years to come.”

Segal’s book is more than a garden-variety political memoir. It has a clear political purpose: to continue his stubborn, 50-year effort to promote a guaranteed annual income. That’s what it was called when he first latched onto the idea just as he became a Conservative activist. Now it’s known as the basic income guarantee, or simply basic income. Segal realized it was an idea whose time had come during discussions at a 1969 Tory thinkers’ conference where David MacDonald was promoting it.

Of course, he has always been a Red Tory, not a “steel-toed” (Segal’s term for partisan politicians) reactionary sort of conservative — the school of Canadian conservatism that includes politicians like Mike Harris who was no friend to the poor.

A key reason for Segal’s long push for basic income for all is his understanding of the cruel insanity that is Canada’s rule-riddled social assistance system. His longtime aide, Rosemary Brisson, gave him a line that the welfare safety net is “strong enough to entangle, too weak to lift.”

Segal’s irrepressible optimism was rekindled into a blaze when Kathleen Wynne’s Ontario government asked him to craft the rationale and design for what became a full-blown, three-city, basic income experiment. The three areas were Hamilton, Thunder Bay, and Lindsay, with the largest contingent from the latter.

To risk another understatement, Segal responded positively. He agreed to do the work, refusing any fee. He needed the right answer when the media asked “How much is this former senator being paid to help the poor?”

Segal held more than a hundred consultations in the summer of 2016. His report, Finding a Better Way, provided essential underpinning for Ontario’s 2017 Ontario Basic Income Pilot. Reiterating their previous promises, all three provincial parties agreed during the 2018 election campaign to support the research to its completion.

Instead, Premier Doug Ford’s new government immediately put its steel-toed boots to the basic income project. Segal writes of his concern for people living with less who joined the research study in good faith, only to be “cruelly disappointed.” The betrayal by his fellow Conservatives was, for Segal, “beyond tragic.”  

Diefenbaker Inspired Segal’s Conservative Path

Segal is a gifted writer who deploys a string of anecdotes like the toy box story to make his point about the screaming injustice that keeps him in the fight for fairness. In 1962 then Prime Minister John Diefenbaker came to his high school class for a special assembly, in the middle of an election campaign. Describing the PM’s passion in vivid detail, Segal explains how Dief’s appearance was instrumental putting him on the Conservative path.

Segal’s trade-union grandfather insisted that the Conservatives were the bosses’ party. That made no difference to a lad who nevertheless recalled his father being denounced by his own dad for buying a cheap suit because it was not union-made.

Segal has had a peripatetic career. Leader of the Progressive Conservative Student Federation. Staffer for Tory opposition leader Robert Stanfield in Ottawa. Deputy minister and secretary of the policy and priorities board of cabinet for Ontario Premier Bill Davis during the Big Blue Machine years. Davis appointed Segal associate secretary of cabinet for federal-provincial relations at a crucial moment in Canadian political history, at the height of the ferment around constitutional repatriation and the birth of Canada’s Charter of Rights and Freedoms.

In the waning years of Brian Mulroney’s administration, the prime minister appointed Segal as his chief of staff. He would later become a Conservative senator for Kingston, appointed by Liberal Prime Minister Paul Martin. There also were stints as professor of policy studies at Queen’s and Master of Massey College at the University of Toronto.

Bootstraps Need Boots is dedicated to his mother Sadye and to his political mentor, the longtime Progressive Conservative, David MacDonald. Fourteen years Segal’s senior, the P.E.I. native would eventually move to the New Democrats.  In portraying his fellow Red Tory, Segal unwittingly describes himself: a mix of “humanity, skill, can-do optimism, infectious idealism, and inspired naiveté…”

Segal’s book reflects the author’s deep understanding of his country. He has travelled widely, especially during his senate years, talking to hundreds of people who share with him the experience of living in poverty. He lucidly explains the hardwired link between poverty and spiralling health care costs. Cutting the first will mean dramatic reductions in the latter.

He admits that there have been setbacks. But this stubborn campaigner for social justice doesn’t seem deterred.

“The battle has not ended,” Segal concludes. 


Jamie Swift is a Kingston writer and author,  most recently, of  The Vimy Trap: Or, How We Learned to Stop Worrying and Love the Great War (with Ian McKay), finalist for the Shaughnessy Cohen Prize for Political Writing.