Coming of Age

Prohibition and the Great Depression

In 1917, to prepare for America’s entrance into the impending war in Europe, President Wilson signed into law the mandatory closure of saloons and other establishments selling alcohol within a five-mile radius of any military installation. Oakville was within five miles of the Veterans Home in Yountville, which was technically a military installation. This proximity meant that all of Oakville’s vintners and saloon-keepers had to close down their businesses. Wilson’s order added fuel to the Prohibition movement, which became the law in 1920, although Oakville felt its effects well before.

Since Napa Valley wines had been a significant part of the inventory in his store, Fred Durrant was now out of business in San Francisco. He returned to the Oakville store in 1921 to a community whose most important in

Then something unexpected happened. Tourists from the Bay Area started driving to the Napa Valley for an extraordinary treat: bootlegged wine and liquor. It was so well known that fermented products could still be obtained in the Napa Valley that the American Legion made a float, “The SS Bootlegger,” with a sign declaring it a rum-runner from St. Helena, “where the good grapes grow.” Alcoholic beverages were available by the jug or the glass if you knew where to look. More than 2,000,000 motorists crossed the newly constructed Carquinez Bridge one year during Prohibition, many of them driving up the county road and past Durrant’s store.

Selling prohibited products to tourists on the way to St. Helena would have been both risky and unnecessary for Durrant, whose honest disposition would have prevented him from breaking the law, even if he disagreed with it. The store was well-positioned to supply sandwiches, sunglasses, hats, maps and more to out-of-town visitors. The promise of Coca-Cola would have been an especially potent lure for travelers.

Travelers could stock up on fresh eggs, dairy products, and farm-grown fruits and vegetables on their trip back to the Bay Area. With access to gardens like Doak’s, Churchill’s and others, Durrant’s wares were fresher than anything in San Francisco. Happy to target the tourist trade with temptations like ice cream, Durrant borrowed money to make upgrades at the store. He added refrigeration units and deepened the store’s footprint. The store became a beacon in an otherwise bleak landscape, at least from a commercial point of view.

Oakville Mercantile remained in business throughout Prohibition. The hated law met its official demise in the state of California on December 6, 1933. By then the national economy had plunged to uncharted depths during the Great Depression. Most of the vintners who did attempt to get back into business encountered rusted-out, inadequate equipment, the absence of winery employees with recent experience, poor grape varieties, market indifference and a host of other problems. Of the 145 wineries in operation in 1918, only a few were legally active in 1933.

Prohibition and the Great Depression had all but ended the market for premium California wine. Vineyards gave way to orchards of walnut and prune. Durrant’s Oakville store served as a local mainstay, just as it had been at the turn of the century. 

Growth and Luxury

To test whether there really was a market for high-end culinary products in rural Oakville, they opened with 75 different varieties of mustard on display. When those flew off the shelves, they added artisan cheeses, fresh herbs, spices, an array of mineral waters, a selection of caviars and other items that had never seen their way into a store in the Napa Valley, let alone Oakville.

While the items for sale at the Grocery evolved from the ordinary to the extraordinary, the Michels were careful not to alter the history and feel of the old building. The old glass-paned candy case remained. People could still charge to their house account, and the post office continued to serve as a local meeting place. Several upgrades were necessary, however, to display their wares correctly. These all came over time, as money started to trickle in. They built an island in the center of the building for preparing sandwiches and added a new cash register. A juicer provided tangy refreshment by the glass. They converted the 8” x 8” stone cellar into a wine shop featuring vintages from small local wineries and selected imports.

Infrastructure features like churches and schools would be essential if Oakville were to grow into an actual incorporated town. There were some indications that this was on peoples’ minds because when all the debris from the fire had been cleared away, other buildings went up on and around the one-acre square. A new store on the corner of the county road and the Oakville Cross Road replaced the old butcher shop. It was a saloon with lodgings of some kind on the second floor. An upgraded blacksmith shop between the new pub and the grocery/mercantile store weened itself from horses and offered autos for hire. Above it was a meeting place, Oakville Hall, that served as a combination town hall and gathering place for community events, like dances.

The Michels installed a feature few people had experienced: a coffee bar with brewed coffee made from fresh beans, rather than percolated from cans of pre-ground. The space was cramped, especially since the coffee fixings shared a wall with the door to the post office.

To facilitate transportation John wanted to rent vans with signage for the store. Pam made salads and other items for take-out lunches, as it was done in New York. She and John grew some of the produce they sold and displayed it in welcoming straw baskets.

John sought out purveyors of obscure ethnic food in San Francisco and located new suppliers for more unusual condiments. Cornichons, olives, yogurts, cheeses and rare herbs and spices found their way into his inventory, much to shoppers’ delight. The best Italian olive oil, imported dried pasta, and artisan vinegar now lined the shelves and filled the baskets, inviting patrons to expand their tastes. Fresh produce and just- baked bread were essential to the business. John found a supplier of baguettes, Passini, which was a novelty in 1974. Where the old store used to carry hot dogs and packages of Hormel cold cuts, the Michels displayed patés and goat cheeses, as well as imported, cured meats usually found only in major metropolitan centers.

The Oakville Grocery was situated very close to the road, and parking was an issue. The owner of the Oak Rail bar and grill rejected their pleas to let patrons use their parking lot. Concerned about the safety of their patrons—and worried that the parking problem might discourage would-be shoppers—John and Pam offered, in 1975, to rent the Oak Rail using the money they borrowed from family members. The owner agreed.

They moved the coffee bar and its associated baked goods to that space and served light lunches and alcoholic beverages at the grill. John began the morning at the Grocery and spent most of his day re-supplying inventory. Pam took over after school let out, while John tended bar at the Oak Rail. At night, Pam cooked for the store as she did her school lesson plans for the next day and also prepped for the cooking class she taught at Silver Oak Winery just down the road. Despite hiring a co-manager, Pam and John did not get much sleep. Then two propitious events in 1976 combined to send torrents of customers their way.

That May, at the respected “Judgment of Paris” blind tasting in France, local Napa Valley wineries did unexpectedly well. This encouraged wine enthusiasts who had written off the Valley years before to come back for a second look. The Paris success dovetailed with a project that Margit Mondavi spearheaded: the Great Chefs program at Mondavi.

Now that the Oakville Grocery had made it possible for Napa Valley residents to buy hard-to-find ingredients, Mondavi realized she could ride the new wave and further the area’s sensory education. She invited some of the world’s most renowned chefs to teach cooking classes at the winery. For a significant fee, food lovers could learn nouvelle cuisine and cuisine classique from a lineup of phenomenally gifted chefs. She established a series of exclusive five-day courses taught by masters of French cuisine as well as American culinary leaders such like Julia Child, Wolfgang Puck, Alice Waters, Jeremiah Tower, Jan Birnbaum, and Thomas Keller.

The Mondavi winery’s in- house culinary team managed the Great Chefs program. They prepped the ingredients, ran the kitchen staff and provided John and Pam with the recipes well in advance so they could stock the shop with the necessary ingredients. People came from all over the Bay Area, and eventually from across the globe.

Operating an ultra-high-end food store had a specific set of perils. Locating suppliers, while difficult, may have been the most natural part of the task. Seasonal fresh produce had to seem abundant and appetizing; dairy products had to be up to date. It became necessary to upgrade the refrigeration again, which exacerbated another problem. Exotic items cost more than common varieties, and procuring them was pricey. Although necessary, improving the refrigeration strained their finances.

Joseph Phelps and Steve Carlin

Successful but overworked, the Michels were relieved when Joseph Phelps, a prominent Napa Valley vintner, saw an investment opportunity in their store. Phelps was relatively new to the Napa Valley. He had been running a construction company in Colorado and had no prior experience in the wine industry when he won the bid to build Souverain Winery (now Rutherford Hill) in the 1970s.

Recognizing the untapped potential in the wine industry, he bought a cattle ranch off the Silverado Trail in St. Helena. In 1973—the same year the Michels bought the Oakville Mercantile—Joseph built a winery of his own. He had developed a keen appreciation for fine foods and was himself an excellent cook; he, therefore, had come to treasure the Oakville Grocery. When he heard from Jean Michels, John’s mother, that business was booming at the Oakville Grocery, but the workload was crushing her son and his family, Joe offered to buy out John and Pam while retaining John as an employee. They jumped at the chance. John promptly repaid Tom May, who stayed on as a silent partner.

To keep abreast of changes in the field, John traveled back to New York and met with the founders of Dean & Deluca, Joel Dean and Giorgio DeLuca. They had opened their “corner grocery store” in SoHo in 1977, offering guests artisanal gourmet specialties similar to those in Oakville. The original Dean & DeLuca was reminiscent of a turn-of-the-century emporium, with spinning fans dangling from the very high ceiling and colorful, lavishly overflowing displays. Their shelving, however, was avant-garde: shiny, chrome-colored “metro wire” that collected no dust and gave the store a feeling of modernity and airy freshness. He also learned of their plans to expand to a much larger and posher store and to branch out to other cities.

When he returned to California, John convinced Joe not only to tear out the shelving and install metro wire (John and Pam did the work themselves); he also went to San Francisco to scout locations for a new Oakville Grocery there. He found a two-story building at 1555 Pacific Street between Polk and Larkin, and Joe leased it. They also considered opening a store in the Phoenix area – which was now home to a booming retirement community – but decided the distance would be too difficult to manage.

In terms of foot traffic, the Pacific Street location was tolerable. (It was in a mixed-use area of homes and small businesses.) As it had been in Oakville, however, parking was an issue. John hired valets to help with it. He chose to manage the store himself, and he selected an enterprising former musician, Steve Carlin, to run the Oakville business in his absence.

The Pacific Street location boasted even more prolific offerings than its Oakville sibling, with more than 100 cheeses, fresh pastries and an expanded selection of mustards and condiments. The charcuterie program was more evolved, with imported cold cuts, fresh sausages, and prime meats, poultry and fish. It attracted the attention of food writers and epicures from near and far. An artist friend of John’s developed a logo: the profile of a “fierce bunny.” 

Food critics wrote lovingly of the San Francisco store. A columnist from the Dallas Tribune extolled its unique inventory in a way that may have left readers wondering if it was a grocery store at all. Despite these rave reviews, the store quickly ran into serious roadblocks. In addition to the parking dilemma, labor issues arose. Most of the employees were young, enthusiastic and eager to please. However, the store was not unionized, the staff received minimum wage, and all the publicity it had received drew the attention of the Teamsters Union. Picketers came, discouraging patronage. The store lasted less than a year. Joseph Phelps and John Michels parted ways, John moving on to develop some prestigious food departments in high-profile settings, among them The Cellar at Macy’s.

Meanwhile, up in Oakville, Steve Carlin was proving to have not only a superb palate but good management skills, as well. Joe Phelps and Tom May financed another round of enhancements, giving the wine program a new home that occupied the entire back section of the store.

The Culinary Boom

As the national economy emerged from the malaise of the 1970s, interest rates fell, and money became more fluid. The idea of escaping modern times and finding a quieter pace of life was appealing, especially to those who could afford to invest in vineyards and wineries. More than 100 new wineries sprouted in the Napa Valley in the 1980s, very much as they had in the years around 1881. Tourism rose throughout the ’80s as more and more visitors discovered treasures in the Napa Valley. The general population was also enjoying an increased appreciation for fine food and drink, thanks to the Oakville Grocery and similar places that were opening elsewhere in the country.

Having before regarded the Napa Valley as too remote, a few first-class restaurateurs were privy to the natural genius of pairing the wine experience with excellent food. Claude Rouas opened Auberge du Soleil in Rutherford in1981, followed by Piatti in Yountville. Soon many other top-rated chefs followed, like Cindy Pawlcyn (Mustards Grill, 1983) and Michael Chiarello (Tra Vigne, 1986). The mutually enhancing and beneficial relationship between good wine and good food sponsored a period of great awakening in the Valley, both economically and culturally. Mercedes Benzes, B.M.W.s, and chauffeured limousines filled the parking lot at Oakville Grocery, and the store prospered like never before.

Oakville was again being recognized as the best of the best, and the staff at the Oakville Grocery was exceedingly knowledgeable. A former employee, Christie Shelley, worked there in her teens after school and on weekends. She recalls:

All the employees were like professors of food. They knew their cheeses, wines and deli goods. I stayed out of the way stocking shelves and sweeping the floor...There was no air conditioning. On summer days in the valley, things heated up. I remember sitting on a milk crate in the large cooler, stocking sodas and making sure the new drinks were in the back and the colder ones up front. One of the food professors walked in holding a paper bag, asking me if I wanted to smell the most amazing thing ever. He was sniffing the inside of this brown bag and practically doing somersaults. Whatever was in there was magical in his mind. I had no idea what it was at first, but it indeed was the most fantastic scent I’d ever experienced in my life. Earthy, musty, sweet and salty all at the same time – truffles imported from France... They were practically out the door as soon as they arrived...


In 1992 the stock market took off, increasing the amount of wealth available for discretionary purchases like high-end wine and fine foods. It also provided funds for research and development in other burgeoning industries, particularly technology. Some who saw fast successes came to Napa Valley with their fortunes.

The Expansion

Joseph Phelps and Steve Carlin believed the time was right to open other Oakville Grocery stores. They tried to avoid one of the more severe problems John Michels had encountered by finding locations with ample parking. They chose Palo Alto (715 Stanford Shopping Center) and marketed their offerings to a younger, more urban crowd than those who typically shopped in Oakville. About six times larger than the Oakville facility, the Palo Alto outpost offered prepared meals like skewered chicken, grilled shrimp, pad thai, and salads composed of hard-to-find, exotic ingredients.

Well-trained deli staff with state-of-the-art equipment cut imported prosciutto, bundnerfleisch and finnochiona into slices fine enough to suit the pickiest gourmet, and patrons could eat their purchases at tables on the nearby patio. They even implemented a loyalty program for “Frequent Sandwich Buyers.” Nicho Ashley was hired to work part-time at the Palo Alto store when she was a culinary school student at San Francisco City College. “I was in awe,” she reflected. “I wondered how much a person needed to know about food to become a manager there. I was hungry to learn everything I could.”

The next store opened at 1352 Locust Street in downtown Walnut Creek (1994), drawing in foodies with a taste for culinary specialties like arancini (fried Sicilian rice balls with ground meat) and soppressata (Italian salami), as well as the expected array of imported chocolates, fine cheeses, homemade soups and obscure condiments. Dinner selections like hot roast beef, leg of lamb Provençal and crispy duck were available to order via the store’s website for pick-up or home delivery.

Encouraged, Phelps and Carlin pulled out all the stops and built a grand Oakville Grocery (5,600 sq ft) in Old Town, Los Gatos, at 50 University Avenue. There they launched more than a dozen Oakville Grocery-branded items, including infused oils and vinegar, condiments, herbs, spices, and even wines, as well as slippers and robes, and they published a mail-order catalog to facilitate purchases.

The new stores had modern amenities like pizza ovens and a rotisserie, in addition to the gourmet deli section that devotees expected. Wine tasting bars took over space where produce might otherwise have been, and patrons could order to-go over the internet or drop in and pick up lunches on the fly. Steve Carlin believed that life had become too “super-charged” for a leisurely, home-prepared meal. In his eyes, who cooked anymore?

In 1997, they opened another branch in Healdsburg, a rural-feeling village of fewer than 12,000 people on the Russian River in Sonoma County. The Oakville Grocery there was well placed on the southeast corner of the historic Central Plaza. Patrons 

could dine on lovingly crafted sandwiches, specialty salads, and other lunch offerings at picnic tables beneath the welcome shade of umbrellas. Here, too, a very generous wine selection was available, including those from the nearby DeLoach Vineyards. The first chef at the Healdsburg store, Jeff Mall, had worked at Jeremiah Towers’ Stars Oakville Café and had a good feel for the kind of operation that would reflect the historic ambiance there, remaining true to the original concept of serving excellent food in a relevant setting.

The flagship store in Oakville, meanwhile, continued to thrive. More than 80% of the Grocery’s guests drove there from out of the Valley. Parking continued to be difficult, especially with the increasing popularity of long limousines, so the Phelps family worked out an agreement with Opus One to swap some land. They demolished the housing units behind the store and installed a driveway with parking spaces that surrounded both the Victorian house and the store.

Woodside Capital Partners

From a sales perspective, the expansion campaign seemed to be working, but from an overhead standpoint, the numbers were less enchanting. While people were willing to spend top dollar for a hand-folded Mezzaluna or hand-crafted Buffalo Mozzarella, landlords were now ready to charge top dollar for renting space. As Safeway and other mass-market retailers began to stock premium products, the law of diminishing returns was apparent. To protect the bottom line, the Walnut Creek and Los Gatos outposts both closed in 2002.

In 2003, Joe Phelps released his control of the Oakville Grocery Company to Woodside Capital Partners, an investment company, although he kept a financial interest in the Oakville Grocery and retained ownership of the land. Carlin left to help develop the Ferry Building Marketplace in San Francisco and then the Oxbow Public Market in Napa, of which he became the majority owner.

Woodside Capital inflated the Oakville Grocery even further. They announced a plan to open 25 new stores in many places across the country during the succeeding five years. To reduce the dreaded overhead, they bought odd lots of discontinued specialty products from all over the world at meager prices and sold them at rates slightly beneath the premium prices Oakville Grocery had charged in the past. They eliminated the deli. They went as far as possible from the central fact of the Oakville Grocery as a pioneering, rural store in the heart of the historic Napa Valley wine country.

In 2006 Woodside Capital decided to try for another Oakville Grocery in San Francisco, this time at 2801 Leavenworth Street. It opened in October with 70 employees and touted a catered Thanksgiving dinner featuring Diestel turkey and fixings, butternut squash and pear soup, stuffed Medjool dates, petite crab cakes, roast garlic mashed potatoes, gravy, artisan bread stuffing with fennel and apples, creamed spinach, maple baked sweet potatoes, and brussels sprouts with pancetta and cippolini onions, topped off with pie from Napa’s Sweetie Pies, among others. The store failed to catch on, closing in March the following year.

The American economy was putting on the brakes, hard. The original Oakville Grocery was doing fine, but suddenly Woodside Capital, now its parent company, was not.

The Restoration

Leslie Rudd: Renovation

In 2007, just as the economy was approaching its darkest hour, an entrepreneur and fine food enthusiast fortuitously stepped in to help the ailing business. Leslie Rudd loaned Woodside the cash to cover immediate expenses and took over ownership of the Oakville Grocery. He closed the Palo Alto store and decreased the stock of imported items at Healdsburg and Oakville.

Leslie Rudd had a sensitive, refined palate and an epicure’s appreciation for food and wine. As his successes in real estate and liquor distribution mounted, he was able to invest in ventures that spoke to his passions. Rudd made a special purchase in 1996: the Dean & DeLuca chain of fine food stores that had so impressed John Michels. He opened outposts of Dean & DeLuca in Charlotte, Kansas City, Tokyo, Taiwan, and St. Helena before selling the chain to a Thai company in 2014.

Rudd loved history. Over the years he had bought and restored quite a few historic buildings around the country. Authentically old, the Oakville Grocery exuded history, even if the wares seemed ultra modern. By 2011, it was all too apparent that the building in its present physical condition had reached the end of its lifespan. Without a solid foundation, proper insulation, and modern plumbing and electricity, the store could not continue to thrive. The 

building’s sag to the southwest was ever more pronounced, and the wall studs seemed held together by the shelves they supported. As one carpenter quipped, all that kept it standing was a habit.

To Rudd, tearing the old thing down was out of the question. It was on the National Register of Historic Places, but even if it hadn’t been, its intrinsic beauty and the history it had seen made it worth saving. Rudd hired Guy Byrne, a contractor sensitive to the painstaking and delicate task of retaining all the salvageable elements. Crews began to dismantle the structure in January 2012 and completed it in May of that year. The Victorian house—renamed the Durrant & Booth house—was also restored and converted into a setting for administrative uses.

Leslie Rudd passed away in 2018, and Jean-Charles Boisset bought the Oakville Grocery and the Durrant & Booth house.