A medical doctor who has practised in conflict zones, Hoskins has plenty of experience having the odds stacked against him, from trying to help child soldiers to talking his way out of life-threatening situations.
He's facing a new challenge now: going into a leadership convention with the smallest number of delegates — just 105 of about 1,800 — and almost certain to be dropped after the first ballot.
Hoskins entered the race as a dark horse candidate, a junior cabinet minister with just three years of politics under his belt. But he remained optimistic about his chances, saying he carries less baggage than his more experienced rivals.
His greatest asset was the 25 years that he spent as a doctor, working overseas and building War Child from the ground up with his wife, Dr. Samantha Nutt, he said.
"The good doctors are among the best listeners out there, and I learned that over the last couple of decades: how to listen," Hoskins said.
"I think that connection is really important, and that real life experience is really important. Especially in a place like Ontario, where we're one of the most diverse places on earth."
Hoskins, 52, is perhaps best known outside political circles as a celebrated humanitarian for his work with War Child. He and Nutt still practice medicine — in addition to raising their seven-year-old son, Rhys — although Hoskins doesn't put in many hours these days.
But his medical skills have come in handy. He jumped to the rescue in the legislature one day when an elderly woman sitting in the public gallery collapsed.
It's the kind of story that's reinforced Hoskins' reputation as a worldly white knight. An Oxford-educated Rhodes scholar, Hoskins work has garnered him the Order of Canada and the United Nations Lester B. Pearson Peace Medal, as well as the Governor General's Meritorious Service Cross.
For three years, Hoskins was a senior adviser to former foreign minister Lloyd Axworthy on issues such as human rights, child soldiers, peacekeeping and the ban on landmines.
He also has some star power with celebrities and musicians that he's met through his humanitarian work. Canadian rapper K'Naan endorsed his friend right off the bat, asking his Twitter followers to join the party to vote for Hoskins.
But Nutt has been one of his biggest boosters, saying his "boundless compassion," courage under fire and "innate ability to lead" has always been a part of his character.
Running a multimillion-dollar international charity has also taught him how to work with a tight budget, which the next premier will have to do to slay Ontario's $14.4-billion deficit, Hoskins said.
He's also quick to say that he's not just a big-city guy, even though he represents the Toronto riding of St. Paul's and has lived in the city for years.
In nearly every speech, he's emphasized his rural roots in Simcoe, where he was born and raised, and his work in northern Ontario as an emergency room and family doctor.
Hoskins was first elected in a byelection that was triggered when former cabinet minister Michael Bryant left politics. The doctor was soon elevated to cabinet as minister of citizenship and immigration. He most recently served as minister of children and youth services.