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For almost anyone other than Jamie Kennedy, September of 2008 was not the best time to hold an optimistic view of the world.

In fact, as we now know after his recent revelations, the superstar chef could have been leading the pessimism vanguard. His high-end restaurant at the Gardiner Museum was turning into a financial disaster as the luxury-lunch market faltered and ceramics admirers demanded something quicker and cheaper than his fastidious, locally sourced cuisine. Huge cost overruns at the recently renovated headquarters of Jamie Kennedy Kitchens soured the positive reviews of the artisanal charcuterie and fancy granola bars at his more budget-conscious Gilead Café.

Meanwhile, the 52-year-old namesake of an ever-expanding food empire was increasingly distracted by his farm property in Prince Edward County, and the dreams of opening a rural restaurant/tavern that could serve as a model for the chef's agrarian ideals. In a buoyant economy, maybe he could have got away with his midlife longings for the simple life and its philosophically pure pursuits. But when the recession caught him in its grip, the compromises were unavoidable: He missed paying his trade creditors, ducked bank loans, and found virtue in looking after his staff salaries rather than redirecting PST and GST money to the provincial and federal governments.

“I expanded too quickly,” he now says, sounding more like a chastened entrepreneur than an artisan whose $6 Yukon Gold fries were the talk of the town. “I was exposed to costs far out of balance with my revenue.”

How badly off is the chef who effectively shut down his restaurant at the Gardiner, where the contract runs to 2011, and will now try to make a go of it with a salad-and-sandwiches café?

“I am in a very precarious position. If someone like the provincial government decides they don't want to play ball, they could force the issue and tip the balance. Bankruptcy is an option, but at the end of the day, the people who lose out are those who trusted me. So it's not a viable choice.”

Yet just nine months ago, the man who can't or won't pay his bills delivered a personal message posted on the website of the Evergreen Brick Works that betrayed none of these internal conflicts. Announcing the opening of the new Chefs' Market he helped develop at the Brick Works' Don Valley site – the message includes a picture of the lean, long-haired chef in full farmer mode – he couldn't have been more optimistic: “These are exciting times in the world of gastronomy,” he wrote. “We have entered into a new era that recognizes the importance of making connections between local farmers and the population of the city.”

Here was a food lover who could set a small emerging farmers' market against a global collapse and find a new era of excitement. Understand that conundrum and you've figured out Jamie Kennedy, a youthful veteran who's managed to occupy the centre of Toronto restaurant culture over almost three decades of economic highs and lows. Foodies with short memories may believe these are the worst of times. But the chef who's known the peaks of Scaramouche, Palmerston, JK at the ROM, the many permutations of the ever-thronged Jamie Kennedy Wine Bar and now the nose-to-tail simplicities of the Gilead Café accepts that there's going to be down time between the great successes.

“Entrepreneurs take risks, they make mistakes,” he says. “I've opened and closed restaurants, I got through the bad times, I survived.”

But this time it's worse – even he acknowledges the seriousness of the situation after his moment of philosophical consolation. When he hosted a food writers' lunch at the Gardiner 11 days ago to acknowledge his plight, his critics felt he was denying responsibility by pointing out the higher costs of the local, artisanal ingredients he favours. Now he's content to accept the blame.

“I've made strategic errors over the last two or three years,” he says. “The responsibility for the precarious position the company is in today can't be blamed on the downturn in the economy or the cost of local food.”

Figuring out where Jamie Kennedy went wrong has preoccupied the Toronto food community, if only because the reality of his predicament contrasts so starkly with his projected aura of success. For Rodney Clark of Rodney's Oyster House, it's a case of Mr. Kennedy's iconic status outdistancing his day-to-day product.

“Jamie's a great person to stand in the pulpit and describe the seriousness of the 100-mile diet, to talk about sustainability and stewardship. His name's on every fundraiser, he's a big draw. But this is a business first, and you don't eat the man's stardom, you eat the man's food.”

For Chris McDonald of Cava, Mr. Kennedy's food activism may have become a distraction. “People forget the food is supposed to be entertaining, that eating is a pleasure. You need to make it fun, to push the politics to the background. Otherwise it gets boring fast.”

Roberto Martella of Grano, a restaurateur who has stayed true to one location and one concept while Mr. Kennedy has worked his way through a dozen or more, observes that “His Achilles heel is that he always wants to do more, to be more.” Mr. Martella is as civically engaged as Mr. Kennedy but much of his activity is restaurant-based, allowing for a certain coalescence of philosophy and business. “Jamie has done so much,” says Mr. Martella of his ally in Toronto's Slow Food movement. “But maybe he's done too much. Now's a good time to keep your head down and do your own thing, the headlines be damned.”

The media reports of his demise don't bother Mr. Kennedy, or so he says. And if he isn't exactly keeping his head down – who else would host a free lunch to quell rumours about his own downfall? – he's at least fixed on trying to make sense of his businesses in a way that would let them to survive, and allow him to realize his Prince Edward County dream.

“We're bringing this back to a human scale,” he says.

The changes at the Gardiner allow him to reduce staff numbers, while supplying the museum café from his Gilead commissary. He's looking for new sources of revenue by selling his charcuterie at The Healthy Butcher and co-branding with Rowe Farms to produce lines of chicken and beef stock. He's set up fair-trade commodity contracts with local growers like the deal that supplies Jamie Kennedy Kitchens with the 60,000 pounds of potatoes it needs for its signature fries. And he's offered to sell the wine bar to his senior managers in what he calls “a correction of this mood of expansion. If the sale occurs, it would help me address my current cash concerns.”

The through line in his working life among the celebrity peaks and the financial troughs has always been a philosophy of local food culture that remains consistent, whether the Gardiner is serving wild striped bass with heirloom carrots in a beurre blanc or just a ham sandwich (but a really good, smoky ham sandwich on Red Fife whole-wheat bread with homemade pickles).

But at some point he took his eye off the basic ingredients. It's clear in talking to him that his original decision to expand gnaws at him as much as the financial fiasco that it produced. “It was a moment where I was seduced by success: The headiness of the wine bar led me to believe I could grow, but I realize now I should have kept things artisanal. I was challenging my own ethos by expanding that way.”

Yet even these mea culpa s lead inevitably to a desire to change, to try something new, to fit the food business and the Jamie Kennedy philosophy more perfectly together. He's longing to make the shift to the Prince Edward County farm he calls home. “I've been involved in this industry for 35 years,” he says, a fact that's hard to accept when you look at him but easy to understand when you consider his restlessness. “The farm is where I want to be, physically and personally, in my life.”

Just don't call it retirement. “It's an experiment in defining the mixed family farm,” he says, “and the model for a new economy.” For Jamie Kennedy, there can be no rural retreat.