07/04/2018 08:17 EDT | Updated 02/23/2019 10:21 EST

Kelly Craft Prizes Common Ground, Friends Say. But Life As Trump’s Envoy In Ottawa Hasn’t Been Easy

"She is trying to do her best, and she’s in a difficult circumstance."

Chris Wattie / Reuters
New U.S. Ambassador to Canada Kelly Craft is introduced before presenting her credentials during a ceremony at Rideau Hall in Ottawa, Ontario, on Oct. 23, 2017.

This feature was first published in July 2018. In February 2019, U.S. President Donald Trump nominated Kelly Craft to be the U.S. ambassador to the United Nations.

When Kelly Craft was growing up, her father, Bobby Guilfoil, encouraged her to think for herself.

"My dad was the kind of person who, Republican or Democrat, he didn't put a label on anybody," her brother Marc says.

The Guilfoils lived just outside Glasgow in central Kentucky (population: 14,000). Bobby farmed and served as the town's veterinarian. He volunteered at the First Christian Church, served on the local board of health, and was active in Democratic politics — becoming, in his later years, chairman of the Barren County Democratic Party.

When Marc, his elder sister Kelly and youngest sister Micah were little, people used to congregate at their home for Guilfoil's famous political pig roasts.

If their dad talked to someone long enough, Marc says, he'd find some nugget of commonality, something on which to build a relationship.

"That's what he was really good at, and that's what he encouraged us as kids to do: find an anchor point, and then build from there. And that's what she does the best."

* * *

She is Kelly Craft, the 31st United States ambassador to Canada, the first woman to hold the job, and the first appointed under U.S. President Donald J. Trump.

Craft has not had an easy time in Ottawa, she has confided to close friends.

In a television interview with CBC soon after she arrived in Ottawa last fall, Craft, who is married to coal tycoon Joseph W. Craft III, said she believed there is "accurate" science on "both sides" of the climate issue. Craft, whose electronic signature has included "Sent from my coal powered iPad," was ridiculed in the press.

For months, it seemed she avoided the media.

Watch: There's 'no better posting' than Canada, says Kelly Craft

Then in February, she gave her first major Ottawa speech at the Macdonald-Laurier Institute annual dinner. Brian Lee Crowley, the managing director of the institute, recalls that Craft and her staff were "quite anxious" to ensure that she would be treated fairly and that the think tank wasn't on the hunt for any kind of "gotcha moment."

She "didn't want to find herself in a situation where she would have to defend the administration or ... be put on the spot before she was really fully conversant with all the files," he said.

Craft stumbled a bit in her remarks. She was received politely, though perhaps not as warmly as previous ambassadors had been. She commented that the Canada-U.S. relationship is as "respectful as ever," even though the signals coming from "the media and thought leaders often suggest otherwise."

The still-unsuccessful-now-on-hold NAFTA negotiations, Trump's insulting tweets and his advisers' personal attacks towards Prime Minister Justin Trudeau, plus the imposition of steel and aluminum tariffs citing a national security clause, have since strained the relationship.

Marc Guilfoil
Kelly Craft's father, Bobby Guilfoil, was a veterinarian and a Democrat.

White House Press Secretary Sarah Sanders said on Monday that the United States had been "very nice to Canada for many years" and Canada had taken "advantage of that."

"It's not easy, the job she has," said John Calipari, the head coach of the University of Kentucky's men basketball team who has worked closely with Craft on campus fundraising. "It's not easy being in that situation."

Her brother echoes the sentiment: "She's in a difficult spot."

During a fireside chat at the Macdonald-Laurier dinner, Craft publicly shared some of her frustrations about working with the Trump White House.

The president, she said, is "free-wheeling, he is charismatic, whichever way you want to take that ..."

Leah Millis / Reuters
U.S. President Donald Trump is greeted by U.S. Ambassador to Canada Kelly Knight Craft as he arrives to attend the nearby G7 Summit after landing at Canadian Forces Base Bagotville in La Baie, Que., on June 8, 2018.

He thinks likes a businessman, she said, and is focused on results.

"I don't think that he is very good at expressing how we are going to achieve those results. I think that would be very helpful if he laid that out for all of us, right?" Craft said, looking at Texas Congressman Pete Sessions sitting next to her on stage.

Last week, the mayor of Ottawa called for a boycott of Craft's Fourth of July party. Jim Watson, who is up for re-election this fall, said it would be hypocritical to rub shoulders with the Americans, drink their wine and eat their canapés while Trump imposes crushing tariffs on Canada and threatens tens of thousands of jobs. Other local politicians and the city's popular anchorman have said they too will shun the event.

The Independence Day reception on the grounds of Lornado, the ambassador's sprawling Rockcliffe residence, was supposed to be Craft's coming out party. The guest list had been pared down, with multiple sources suggesting fewer than 1,000 people invited — a quarter of the usual invitees — but it was still the largest bash Craft would host this year. Last Friday, she spoke to her brother on the phone expressing concern her party would be a flop.

Marc Guilfoil
Marc Guilfoil is shown with his sister, Kelly, in a family photo from 1966.

Watson's comments came a week after an offsite mail supervisor discovered an envelope addressed to Craft containing a suspicious white powder and a letter threatening to kill her if she did not resign from her post.

"It perked her ears up a little bit, but I think she has full faith in [the security] she's got around," her brother said.

* * *

Craft, of course, has no intention of resigning.

When she took the oath of office last September, Craft spoke about answering a "nation's call." Every day probably wouldn't be perfect, Craft predicted; there would be complicated and unpredictable moments. But she pledged to lead every day with "a servant's heart."

She spoke of the appointment as a dream she and Joe shared.

More from HuffPost Canada:

Like many of her predecessors, Craft was rewarded with the ambassadorship to Canada because of her contributions to the president's campaign. Together, the Crafts donated more than $2 million towards Trump's election and inauguration.

Craft, a longtime Republican fundraiser in her own right, donated $265,400 to the Trump Victory fund.

That either of them was appointed wasn't a surprise, Calipari, the basketball coach, said. Craft had raised the possibility with him before her nomination, he said.

Joshua Roberts / Reuters
U.S. Ambassador to Canada Kelly Knight Craft speaks after she was sworn in, as her husband Joe Craft watches in Washington on Sept. 26, 2017.

Ron Kaufman, the Republican national committeeman for Massachusetts, said the couple did not donate the most money to Trump but their contributions were "helpful."

More than the dollar amount, Craft was seen as an early embracer of Trump who brought along her ties to George W. Bush's campaign. She had raised money for the 43rd president, "did a great job with him, and as you know was appointed to the UN," Kaufman noted, casually referring to the tit-for-tat relationships that exists in political financing south of the border.

In 2007, Bush named Craft an alternate delegate to the General Assembly of the United Nations, meaning she could address the assembly on behalf of the United States.

The Crafts helped give Trump "credibility in a lot of people's minds," Kaufman said. Craft initially backed Florida Senator Marco Rubio for the Republican nomination. She and Joe had been Kentucky finance co-chairs for the 2012 presidential bid of former Massachusetts governor — and later Trump critic — Mitt Romney.

Although Craft didn't know Trump until he became the Republicans' presidential nominee, Kaufman, who served as White House personnel director under president George H.W. Bush, said he wasn't surprised she was named ambassador.

"There weren't many people of that ilk who had respect from a large spectrum of people and [were] loyal and faithful to him. So that was not a hard pick."

"I think she thought that the president was going to ask Joe to take the job, but the rest of us were not surprised that he asked her," Damon Thayer, the majority leader of the Kentucky state senate, told HuffPost Canada in an interview.

Her friend, Selma Owens, says Craft received the plum post because of her skill set, not because of Joe.

"Kelly is a very bright woman and has the ability to get a number of things done by herself."

Chris Wattie / Reuters
Joe Craft watches as his wife, new U.S. Ambassador to Canada Kelly Craft, speaks following a ceremony at Rideau Hall in Ottawa on Oct. 23, 2017.

Joe, 67, is the president and CEO of Alliance Resource Partners LP, the seventh largest coal company in the U.S., and federal and state records show, he has been donating to Republican and coal-friendly politicians for years.

In a 2010 documentary, he explained the reasons for his largesse: "The critical issue that we are going to have to look at is what happens at elections, because the only thing, in my view, that can impede the growth of coal gets back to bad public policy."

Last year, Joe was in attendance when Trump declared the "war on coal is over." He was sitting in the front row, according to The New York Times, when his close friend, embattled Environmental Protection Agency head Scott Pruitt, announced a rollback of former president Barack Obama's coal regulations. Recently, that friendship with Pruitt, someone he socializes with, donates to, is regulated by, and frequently lobbies, has been the subject of a Times investigation.

Friendly politicians aren't the only ones who've benefited from Joe's generosity. The University of Kentucky is dotted with symbols of his gifts:

Together, the Crafts have also co-founded the Craft Academy for Excellence in Science and Mathematics at Kentucky's Moorehead University, a special program for gifted high school students.

"She cares about the kids," offered Calipari.

Jonathan Ernst / Reuters
University of Kentucky men's basketball coach John Calipari, right, attends a U.S. Senate Foreign Relations Committee hearing in support of U.S. President Donald Trump's nominee to be ambassador to Canada, Kelly Knight Craft, on Capitol Hill in Washington on July 20, 2017.

In 2010, Joe told PBS that his heart was just consumed with giving back.

"I'm a giver," he said. "I've been fortunate to have the ability to give, and that's what I want to do."

After a divorce, Joe was bumped from Forbes' billionaire list in 2012, which pegged his net worth at $625 million.

Christine Trout, the commissioner of Kentucky Department of Alcoholic Beverage Control and a friend of Craft's, says the couple, who tied the knot in April 2016, share a commitment to public service.

"They didn't get where they are overnight and alone," she said.

* * *

Kelly Craft was one of those little girls who was always seeking some new world to conquer, says Cecile Garmon, a close friend of her late mother, Dale. (Like Bobby, Dale died in 2011.)

"At night when we'd be playing bridge out at her house, Kelly would come running with some exciting story about something that happened in school or to her. She was so energetic about it that you couldn't help but stop what you were doing and listen to her," Garmon recalled.

She was a kind child, charming, courteous and lovely to her elders, Garmon said, laughing.

Her brother Marc, now the executive director of the Kentucky Horse Racing Commission, compares Craft to his childhood hero: L.A. Raiders football player Howie Long.

"What made him so good was he didn't think he was. He just kept going. That's Kelly. She just keeps striving, she wants to be better tomorrow than she was today."

Marc Guilfoil
Kelly Craft is shown riding her favourite horse, Playboy.

Craft was an active child. She played the clarinet in the Glasgow Scottie Band, was involved in student government, and liked to ride horses — her favourite being a handsome gelding named Playboy.

When she was three years old, her grandfather Bill Little, her mother's father and a cattle farmer from Alabama, gave her a pony. It was a "Daddy Little" tradition, and one he continued with all seven of his grandchildren. The Guilfoils had several acres of land outside Glasgow, and her father often brought home horses that people no longer wanted or couldn't afford.

Craft loves horses. She still rides and is a fixture at the Kentucky Derby. Just last this weekend, she tweeted pictures from the Queen's Plate at the Woodbine racetrack.

"There is nothing bigger in Kentucky than basketball, unless it's horses," Garmon said, over the phone. "Horses, basketball and bourbon are the main things we have in Kentucky."

Kentucky's bourbon industry and the 17,000 people who work in the sector have found themselves in the crosshairs of Trump's trade war. The European Union and Canada slapped retaliatory tariffs on the spirit, and newspaper articles all over the United States suggest tough times are ahead. Europe is the largest export market for bourbon.

It all weighs heavily on Garmon's mind. "Maybe it's understandable, but it is not very pleasant for us."

Craft, no doubt, knows the impact retaliatory actions over Trump's tariffs on steel and aluminum will have on her state. A proud Kentuckian, she frequently notes that Canada is the state's No. 1 export market. More than 112,000 jobs are dependent on direct investment from Canada, according to the Northern Kentucky Chamber of Commerce.

Garmon, a staunch Democrat, said it was "quite a shock" to discover Craft had become such a strong Republican.

"I've heard her say that her parents taught her to think for herself, and I imagine that's true.... They'd be very proud of her. I know they would, as we are."

Marc Guilfoil
Kelly Craft is shown with her mom, Dale, and younger sister Micah.

Marc suggests the conversion to republicanism happened sometime in university. She told a local newspaper that she "just kind of evolved in my philosophy."

After high school, Craft moved to Lexington to attend the University of Kentucky. She graduated with a bachelor of arts in 1984. Two years later, she married David Moross, now the CEO of a private equity firm, with whom she has a daughter, Mia.

This April, Mia, who runs a jewellery company in New York City, gave birth to Craft's first grandchild, Noa.

In 1992, Craft married orthodontist Judson Knight. Together, they have a daughter, Jane Brady, who is active in grassroots politics.

Earlier: PM Trudeau meets Kelly Craft

Selma Owens met Craft about 20 years ago when they served on the board of the city's Living Arts and Science Center.

"Whatever she is involved in, she gives it her all. And it doesn't matter if it is a cocktail party for 20 friends, or a fundraiser for a charity she cares about, she just gets involved," Owens said.

Craft's personal donations to the national Republican party began in 2004, federal records show, when she gave to the Bush-Cheney re-election effort. Before that, she was mostly active in local politics and civic causes: helping the poor, raising funds for the arts.

She threw herself into politics, making a name for herself raising money for the presidential ticket as well as for then-governor Ernie Fletcher, congressmen Hal Rogers and Ron Lewis, and U.S. Sen. Mitch McConnell (now the Senate majority leader).

In an interview with the Glasgow Daily Times, Craft reportedly said she found the "mixture of people and personalities" in political circles a "powerful draw."

To this day, McConnell is a close contact. U.S. Vice President Mike Pence and his wife Mary are friends. Paul Ryan, the speaker of the House, is another benefactor of the Crafts.

In 2005, Craft also started a consultancy business, Kelly G. Knight, LLC.

... she is one of those people who has the gift that when she is talking to you, you feel very important ...Lindy Karns

"She helped connect people. Like, if you had a red shoe and you wanted to sell it to somebody that wanted red shoes, she'd make the contacts," Owens said.

That year, she also met Joe. Together, they spread their fundraising wings and dug deep into their own pockets.

Her friends say Craft has a particular knack for making everyone feel welcome and is masterful at bringing people together.

"She walks in, she's tall, she's attractive, she's dressed in white, usually, often, and she is one of those people who has the gift that when she is talking to you, you feel very important, right?," says longtime friend Lindy Karns. "You feel very in the moment and very cared for and so you want to turn around and reciprocate in some way."

'Coco Sparkles'

Craft is the kind of person who thinks of the details, say those close to her. If someone has a family in the hospital, she'll send food. If she learns it's someone's birthday, she organizes a last-minute cake.

When Marc was in Ottawa this spring, his sister dispatched him to get cookies, snacks, water, and soft drinks. While looking for a hose to water her hydrangeas, Craft had discovered the residence's security staff used the garage as a break room — and she wanted to stock their fridge.

Joe's grandchildren call their step-grandmother "Coco Sparkles."

Karns says it's because Craft spreads cheer. "Wherever she goes, it is more interesting, more fun, and even the children see that."

Chris Wattie / Reuters
Kelly Craft meets Foreign Affairs Minister Chrystia Freeland at the Lester B. Pearson Building in Ottawa on Oct. 23, 2017. REUTERS/Chris Wattie

The two met some 15 years ago at a charitable fundraiser for the library. They worked closely together, with Karns doing the books for her company and her personal taxes.

When she was first appointed as ambassador, Craft asked Karns, who had majored in English literature, what she should read to familiarize herself with Canada. So works by Margaret Atwood and Alice Munro found themselves on the ambassador's reading list.

Craft has impressive stamina — she runs about 13 kilometres every morning, even in the winter when, to her delight, the RCMP plows a trail for her. But she's also cautious, her friend says.

"It is her nature to study and to try to figure out what the right thing to do is," Karns said. "I wish there was a lot more caution and just everyday civility. I like a culture where people are polite, and she is an exceedingly polite person."

'A good southern lady'

Garmon describes her as "a good southern lady": poised and polished. She's particularly proud Craft still pens handwritten thank you notes.

What makes Craft a great fundraiser, says Kaufman, who asked her to join the Romney 2012 campaign, is that she doesn't do it for the credit.

"She doesn't brag about it," he says. She's a good team member who spreads the credit around. She's reliable, fun, responsive, and nice, he adds.

"People like her, and trust her, which is hard to find sometimes in politics."

* * *

Owens and Craft speak or text at least once a week.

"What I do right now is more like 'encouragement.' Like 'I know it's tough' or 'I heard this and it was great' ... I mean I don't get involved with what she has to do, but I do try to support her in whatever way I can. 'Cause it's a tough job."

Owens, a Democrat, says Craft has no interest in sitting in an ivory tower — she wants to be involved.

"She has her own opinions, I am sure," Craft's friend adds, "but she does what is required of her by the State Department and what she feels she needs to do for diplomacy."

Last week, after the Ottawa mayor's call for a boycott, Craft wrote an op-ed in The Globe and Mail expressing understanding about Canadians' anger towards the tariffs, as well as confidence that things would all work out in the end.

Some might have viewed it as naive; others, optimistic.

Chris Wattie / Reuters
Prime Minister Justin Trudeau and U.S. Ambassador to Canada Kelly Craft react during a meeting in Trudeau's office on Parliament Hill on Nov. 3, 2017.

If Craft is lonely in Ottawa, her friends haven't felt it. Many have come up to the city for a visit, family has stopped by. Joe flies frequently back and forth on his private plane to Oklahoma, where his company is headquartered, and to Kentucky.

Kaufman, who serves as a sounding board for Craft, declined to comment on her personal views of the situation.

She's not in the captain's seat, he said.

"You are the president's representative. You are not a policy-maker. You can be an influencer. You can be someone who is at the table and can give your thoughts. In the end, your job is to carry out what the policy is ... whether you agree with it or not."

In the end, Kaufman said, her job is to safeguard the relationship.

"She knows lots of stuff but doesn't say anything. That's why she is a good ambassador."

Graham Hughes/Canadian Press
U.S. Ambassador to Canada Kelly Craft speaks to the Montreal Council on Foreign Relations on April 17, 2018.

Canada's ambassador to Washington, David MacNaughton, has high praise for Craft.

The two speak about four times a week, he says. "She is very helpful in trying to be constructive in what one might say is a fairly challenging time, to put it mildly," he told HuffPost on Tuesday.

While both governments remain at odds on trade, bilateral co-operation continues on a number of fronts. Craft is "honest," he said. "There is no side to her at all."

He suggests it is difficult for the new ambassador to be thrust, front and centre, into a diplomatic spat for which she has no training.

Canadians shouldn't bemoan her, MacNaughton added. "She's gone out of her way to be helpful." When he's had meetings that were difficult to set up, she's helped open doors.

'She's a good woman with good intentions'

"She is trying to do her best, and she's in a difficult circumstance.... She keeps a smile on her face."

Calipari hopes Canadians give her the benefit of the doubt and get to know her.

"She's a good woman with good intentions."

Marc, Craft's brother, just hopes people show up to her party.

"I don't want it to be a complete failure."