Former Chicago Sun-Times publisher John Cruickshank, shown here in 2004, holds up a copy of the first edition of the Chicago Sun newspaper, dated December 4, 1941. Credit: John J. Kim/Sun-Times

President Trump slapped a 20 percent tariff on softwood imports from Canada Tuesday, and John Cruickshank’s phone started ringing.

“This is essentially a billion-dollar tax on American home buyers,” Canada’s new consul general in Chicago tells me, as he told callers who wanted to know what to make of the tariff. “This is the Trump lumber tax. He’s raised a tax without saying he’s raising taxes.” Jobs will be lost, Cruickshank says—lumbering jobs in Canada and construction jobs in the U.S.

But Cruickshank doesn’t sound all that excited. Canada and the U.S. do $2 billion worth of trade every day, he tells me. Issues arise. Softwood prices have been a bone of contention between the two countries for decades.

“I was writing about softwood lumber for the Globe and Mail back in the 1980s,” he says.

Tht’s because before he was a Canadian diplomat, Cruickshank was a newspaperman.

The first time Cruickshank came to Chicago, in 2000, he arrived here from Vancouver to be vice president for editorial at the Sun-Times. He answered to Conrad Black, CEO of Hollinger International, and Black’s number two, David Radler. A few years down the road, both men would be overthrown by stockholders and eventually sent to prison for fraud. Their scheme involved selling off the Hollinger papers, writing gratuitous noncompete clauses into the sales contracts, and thereby sluicing into their own pockets millions of dollars that Hollinger shareholders considered rightly their own. Cruickshank went back to Canada in 2007 and after a year at the Canadian Broadcasting Corporation became publisher of the Toronto Star.

Now, back in Chicago as consul general, instead of two felons in training, Cruickshank represents Prime Minister Justin Trudeau, possibly the most popular politician in North America. To Trudeau’s American admirers he’s everything President Donald Trump isn’t—enlightened, level-headed, and intelligent. Also handsome and witty. (Consider this viral video that finds Trudeau fielding a question about quantum computing.)

I ask Cruickshank how the Chicagoans he’s getting to know all over again speak of their president and his prime minister?

“It’s way too early,” Cruickshank says. Besides, “It’s not my role to reflect American attitudes back to Americans.” (Which it was that when he ran a Chicago newspaper.) He does say this about Trudeau: “As a journalist I watched the rise of Justin Trudeau and had opportunities to meet with him. He is, when you get to know him, every bit as impressive as when people see him from a distance mirrored in the media. He’s a remarkable guy.”

As for Trump, he speaks generously of him back in the day—when Trump came to Chicago in the early 2000s and bought the Sun-Times site along the Chicago River where Trump Tower now stands.

“I was very struck by his personal charisma,” says Cruickshank. “I remember we had an event where he was launching the project, and the Sun-Times people were there and it was fascinating to see all the folks lined up to see him, including all the waitstaff from the hotel. He had that attraction for people, he spoke with incredible enthusiasm, and people were really excited by it.”

And as for Black and Radler, Cruickshank generously recalls his years at the Sun-Times as an era when “a great, great staff was doing tremendous stuff” despite dwindling circulation, vanishing advertisers, and the shenanigans of the owners.

Cruickshank says he knew Conrad Black “not terribly well.” Until he was mired here for the 2007 trial, Black didn’t come around much. His offices were in Toronto and his heart in London, where he held court as Lord Black of Crossharbour, media titan, historian, public intellectual, and stalwart of the House of Lords.

Publisher David Radler split his time between here and Vancouver, holding down the fort in Chicago about two weeks a month. Minions would remember him for shutting down the escalators to save a few nickels; Cruickshank would recall the time when Radler was asked how to get rich and answered by scooping up the sugar and Sweet’N Low packets from his restaurant table.

After Radler was booted out Cruickshank became publisher. He quickly realized the Sun-Times‘s way of dealing with its sagging circulation had been to persistently lie about the size of it. In 2005 the Chicago Headline Club gave Cruickshank its ethics award for going public with his discovery. “Under his leadership,” said the citation, “parent company Hollinger International disclosed the overstated circulation figures and set aside $27 million to reimburse advertisers.”

After Cruickshank resigned from his post in Toronto a year ago, he reminisced about how he’d got the same job at the Sun-Times. Of all the possible candidates, he said, he “was the only one who wasn’t under FBI investigation at the time.”

When the new Trudeau government offered him the post of consul general in Chicago, “I just jumped at it,” he tells me. His two kids had been educated at the University of Chicago, and one of them still lived here. Cruickshank and his wife, Jennifer Hunter, still had their town house in North Center.

I ask Cruickshank to compare the oft-compared cities on the lake. Is Chicago, in the shadow of New York, a more parochial city than Toronto, which dominates the Canadian economy?

“That’s not my experience of Chicago at all,” he replies. “One of the things I was so struck by when I first came here is that every Chicagoan I met believes they could be the world’s best at what they do. They could contribute on a global level. It’s something Canadians don’t grow up with, coming from a different political and social culture.”

But now Chicago is beset with economic woes, I remind him. He responds obliquely:

“I’m sitting here looking out the window onto Maggie Daley Park,” he says. “That wasn’t here when I left. And I don’t think the Renzo Piano extension to the Art Institute was either.”

Chicago’s getting along.