Virginia gubernatorial candidate Terry McAuliffe poses in front of a sidewalk bookstore in Havana, Cuba, during his April 2010 trade mission to Cuba. The books behind McAuliffe were displayed in crates that once held Virginia apples. (Obtained by the Washington Post)

Terry McAuliffe has always fashioned himself a master salesman. He could pitch anything.

Then he went to Cuba.

McAuliffe said he journeyed to the island to sell Virginia wine and apples. Yet the Cubans scoffed at his propositions during the April 2010 visit, unmoved by the full-frontal style of persuasion that has long powered McAuliffe’s success as an investor and political rainmaker.

Cuban officials not only rejected McAuliffe, but in meeting after meeting lectured him about the supposed ill effects of the U.S. trade embargo on the island nation.

In many ways, the three-day adventure was classic McAuliffe, offering a taste of the freewheeling, even impulsive, style the Democratic candidate for Virginia governor could bring to the executive mansion if he is elected next week.

He was, in effect, winging it — relying largely on personal charm and hoping for the best, even as many of those around him say they saw little chance for success.

The trip had been intended, at least in part, to erase the sting of McAuliffe’s dismal showing in the gubernatorial race the previous year while showcasing his deal-making skills and home-state advocacy in advance of a second run for office. After it all fell apart, McAuliffe stayed in his permanently upbeat sales mode even as his travel companions privately lamented a journey that was more fiasco than triumph.

McAuliffe returned from Havana with a rosy report: “We got them to agree to open up the market for Virginia wines,” he told The Washington Post at the time. “We are going to export Virginia wines to Cuba for the first time ever.”

In reality, the sales trip was a bust.

“It was like, ‘What just happened?’ Were we rolled?’ ” said Blaze Wharton, a McAuliffe friend and Utah-based lobbyist who organized the trip for McAuliffe and a handful of politically connected business friends.

“We were all under the impression that it would work out,” Wharton said. But, he added, “it went nowhere.”

Why McAuliffe chose Cuba, a communist-led island with a moribund economy, as the place to prove his mettle as a champion of Virginia commerce is a curiosity. Any trip to Cuba, which is still designated a state sponsor of terrorism by the U.S. government, brings complications — particularly for a figure with McAuliffe’s deep ties to America’s political elite. He is a close friend and adviser to Hillary Rodham Clinton, who was secretary of state at the time of the Cuba trip and, should she run for president, would be courting Cuban-American voters wary of contact with the regime there.

McAuliffe, now waging a campaign in which he presents himself as a skilled deal-maker and cheerleader for Virginia businesses, rarely if ever mentions his one venture since the 2009 campaign to sell Virginia products abroad.

McAuliffe’s campaign declined to make him available for an interview. Neither his campaign nor the organizers of the trip could provide the paperwork that McAuliffe was required to file with the U.S. Office of Foreign Assets Control to obtain a license to travel to Cuba, saying they no longer had copies. An OFAC spokesman said the office does not comment on specific licenses.

His spokesman, Josh Schwerin, said McAuliffe had been invited by Wharton to make the trip “and thought it would be a good chance to advocate for Virginia wine and apples.”

Schwerin said Cuban officials expressed interest at one point in a “Virginia wine expo.” But, Schwerin added, “it never came to fruition.” Schwerin said McAuliffe had no financial interest in the trip and was not compensated for his efforts.

Wharton said he had grown interested in seeking business opportunities in Cuba. The United States has allowed certain food exports to Cuba ever since Congress loosened the Kennedy-era embargo in 2000. Wharton said he pitched McAuliffe on the idea of a trip, and McAuliffe, eager to play the role of Virginia booster, immediately began pondering who he might invite from the state.

“Let’s put something together,” Wharton recalled McAuliffe saying.

McAuliffe spoke by phone with Todd Haymore, Virginia’s agriculture secretary, who provided an overview of the state’s growing trade relationship with Cuba, including the exports of soybeans and apples.

Wharton said he financed much of the trip. McAuliffe paid his own way, Schwerin and Wharton said, reimbursing his friend $2,500.

But the two Virginia businessmen that McAuliffe had hoped to showcase on the trip both backed out at the last minute.

Henry Chiles, owner of Crown Orchard near Charlottesville, told trip organizers he had to tend to his crop because of a cold snap. Jim Turpin, who opened a small vineyard four years ago in Lovingston, said he decided selling to the island nation wasn’t a good fit for his business.

“With a name like Democracy Vineyards, I didn’t think it would sell very well in Cuba,” Turpin said.

McAuliffe went ahead anyway.

Over the course of three days, the delegation met with officials from the Cuban trade agency, Foreign Ministry and other departments. The sessions, some lasting well over an hour, would begin with long speeches from Cuban officials about how the U.S. trade embargo has ravaged the island’s economy, according to participants..

Officials at Alimport, Cuba’s official trade agency, did not seem the least bit interested in learning from McAuliffe about Virginia apples or wine — or any potential business deal, according to people familiar with the meeting.

McAuliffe at one point grew visibly exasperated. He interrupted an Alimport official’s discussion of the embargo and pleaded for time to speak. “I came here to talk about apples and wine,” he said, according to participants in the meeting.

Wharton said he was perplexed at how unresponsive the Cuban officials were to McAuliffe’s efforts. After all, participants said, the consultant that Wharton had hired to arrange the meetings, longtime Cuba expert Kirby Jones, had e-mailed the group before the trip to say that deals were “very possible” and that they should be prepared to sign contracts.

“We’d get into these meetings, and Terry was Terry,” said Wharton. “He was really aggressive on the apples and the wines.”

Few of the executives in the delegation expected to do much real business there, said one person familiar with the trip who, like several others friendly with McAuliffe, spoke on the condition of anonymity in order to freely discuss the goings-on. Most participants were excited to experience Cuba.

The meetings were “pretty perfunctory,” said one person with knowledge of the trip. “I bet you a billion dollars there was not one more phone call made [following the trip] about doing business with Cuba.”

Tensions were mounting, however.

On the last night, Wharton confronted Jones, the consultant. Jones, who got to know Fidel Castro while interviewing him for TV documentaries in the 1970s, ran a Bethesda-based consulting firm specializing in helping U.S. businesses navigate Cuba’s regime.

Wharton said Jones tried on several occasions to steal time alone with McAuliffe, including insisting at one point that only Jones and McAuliffe could attend a hastily arranged visit with Cardinal Jaime Ortega, the top-ranking Catholic prelate in Cuba.

The argument escalated, in public, on the patio of the famed Hotel Nacional in Havana. Wharton’s voice rose and he cursed at Jones. “You’re fired,” Wharton recalls yelling.

Jones said he did not recall trying to have time alone with McAuliffe.

“Blaze was very upset, but I basically ignored him,” Jones said.

Jones, who has been leading business delegations to Cuba for more than 30 years, said McAuliffe’s lack of success was typical for a first-timer. Cutting deals with the Cubans, he said, often requires aggressive follow-through and return visits.

Still, Jones said the Cubans recognized that McAuliffe was no ordinary visitor.

“He’s close to the Clintons, and everybody knows that,” Jones said. “And Hillary Clinton was secretary of state at the time, so naturally there’s an interest.”

A Clinton spokesman said the former secretary had not been aware of McAuliffe’s trip at the time.

The meeting with Ortega was the lone high point of the trip, participants said.

Several members of the delegation accompanied McAuliffe to the cardinal’s ornate offices. They said the visit was a thrill for McAuliffe, who is Catholic. He autographed a copy of his 2007 memoir, “What a Party!” for the cardinal, and, flashing a broad smile, posed for a picture with Ortega beneath a giant framed photo of the cardinal with then-Pope Benedict XVI.

Back in Virginia, expectations that McAuliffe would sell anything to the Cubans were low.

Officials at Virginia’s wine marketing office had helped prepare materials in advance of the trip. But when Turpin, the Democracy Vineyards owner, backed out, office officials say never heard about the trip again.

In general, the mere suggestion that the poor, communist-led island might prove receptive to Virginia wine is enough to make even the industry’s fiercest advocates chuckle. State officials routinely bring along a wine display when they travel to an annual exposition in Cuba, but “only as a goodwill thing,” said Annette Boyd, head of the state’s wine marketing office.

“We laugh about it,” she said. Describing Cuba as more of a “rum culture,” Boyd said sarcastically: “Virginia wines go so well with Cuban cigars.”

Turpin, a former lobbyist who served as a co-chair of McAuliffe’s 2009 campaign, had all but forgotten about the trade mission on which McAuliffe was representing his company.

Once Turpin opted out, “I just kind of backed away from the whole thing,” he said.

But shortly after McAuliffe returned to U.S. soil, he phoned Turpin with an update.

“I remember getting a typical Terry call,” Turpin said, “that everything went great.”

Manuel Roig-Franzia and Alice Crites contributed to this report.