It was a Sunday afternoon in early November 2015 when David Plouffe emailed his fellow former Barack Obama campaigner Matthew Barzun, typing “Mr ambassador” in the subject line.

Plouffe was working for Uber, and Barzun had been rewarded for his fundraising efforts for the US president with the plum job of American ambassador to the UK.

“Hope you and your family are well. I will be in London Dec 9 and 10. Any chance you could host the event you kindly suggested with influencers one of those days? Uber, Trump, Clinton etc lots to discuss … David.”

Barzun obliged. “What fun!” the ambassador pinged back. Few people turned down Plouffe when he called in favours. It was just one example of how Uber leveraged Plouffe’s reputation and his access to the Obama network to promote its agenda across Europe and the Middle East, according to documents in the leaked Uber files.

The embassy staff organised an event in December built around Plouffe giving a talk on the gig economy, and they invited the business minister Anna Soubry, the shadow business minister Kevin Brennan, influential MPs, government officials, journalists and business people.

During the trip, Plouffe did the rounds for Uber, going to meet the BBC, the London mayoral candidate Zac Goldsmith and executives of a potential Russian investor in Mayfair, as well as giving a talk at the Institute for Public Policy Research thinktank, calendars in the leaked documents show.

All standard fare for Plouffe, an A-list political operator who had joined Uber the year before, bringing with him a contacts book to die for and the political nous and clout sought by Uber’s then chief executive, Travis Kalanick.

Kalanick wanted someone to help Uber take on the “big taxi cartels”. Plouffe, who had led Obama’s successful campaign for the White House in 2008, was ideal.

A campaigner by trade, Plouffe became one of the central figures in Uber’s global lobbying effort, using his experience to get the company access to leaders, officials and diplomats. Uber also relied on another Obama alumnus as a consultant for political advice, Jim Messina, who had served as Plouffe’s deputy and first introduced him to Kalanick. The files suggest that in some cases Uber tried to use him to gain access to public officials.

Helping to ‘move the needle’

A call here, a meeting there. The well-targeted email to open a door that might otherwise have been closed in cities and countries where Uber was in trouble.

An examination of tens of thousands of leaked internal Uber emails and communications gives rare insight into the company’s behind the scenes manoeuvres; the then Italian prime minister, Matteo Renzi, his Spanish counterpart, Mariano Rajoy, and the ruler of Dubai, Sheikh Mohammed bin Rashid al-Maktoum, were among those Uber sought to gain access to, sometimes with mixed success.

In their different ways, the leaked files suggest, Plouffe and Messina promoted and advised Uber in places where it faced toughest resistance, at times infusing an aura of legitimacy around a company that was known for openly flouting regulations and laws.

Their work for the company appears to contradict the spirit of the Obama administration’s pledge to bring to an end the unsavoury use of cozy government relationships to enhance the positions of companies.

Files show Plouffe going from country to country to help Uber in its relentless campaign to break open the transportation sector. He appeared to be a big believer in the Uber project, which he joined in 2014 as senior vice-president of policy and strategy.

“When you walk thru Uber’s HQ in San Francisco, the place is pulsating with young, brilliant and dedicated employees who believe they are part of doing something historic and meaningful,” Plouffe said in a blogpost announcing his job. “It’s a feeling I’ve been fortunate to experience previously.”

Over the next two years, the files show his interventions in certain countries seemed to help turn the tide for Uber – Mark MacGann, the company’s chief lobbyist in Europe, the Middle East and Africa, described his work in UAE, for instance, as “amazing”. Plouffe’s visit to the region in 2015 “had really helped move the needle” at a time when Uber was “on the cusp” of enforcement against UberX in Dubai, according to one email exchange.

The leaked files show clearly how Uber sought help from US ambassadors known to both Plouffe and Messina to help smooth over relations in cities where Uber faced trouble. This made perfect sense – often the diplomats were big Obama donors. Dating back to 2014, Uber had seen sitting and former US government officials as key to its expansion plans, according to a leaked memo contained in the files that was titled “Leveraging the US government to support Uber’s international business”.

The email from Plouffe to Barzun in 2015 was one obvious example. There were others, too.

In France, Plouffe was told in 2016 by MacGann that Uber needed the US ambassador to France, Jane Hartley, to “intervene” on issues related to Uber’s rival Heetch. A former Uber official said the company’s outreach to Hartley reflected an effort to provide an “update on the business”.

When MacGann asked Messina in a leaked message that July if he had any messages for Hartley, one day before an appointment, Messina responded: “Tell her I love her,” and later: “We did give her FRANCE.”

Uber was also keen for Plouffe to have a quiet word with Tim Broas, the US ambassador to the Netherlands, after one of the company’s executives raised concerns about a “recent escalation of action against us in NL (including arrest of senior staff)”.

“Probably not a lot he can do through official channels, but worth getting him up to speed so he can be our champion in private conversations,” Corey Owens, who was head of Uber’s global public policy at the time, said in an email to MacGann.

(Messina also knew Broas, but was withering about him. “If the town of USELESS had a mayor, Broas would be it,” he wrote in an email in April 2015.)

Plouffe denied in a statement that any of the public officials he sought out while he worked at Uber were responsive because of his previous relationship and work for the Obama administration.

“Let me tell you, you get in the room with a transportation minister, I don’t care where it is, state capitol, city council, European capital, African country, they don’t care what I or anyone else did before,” Plouffe said. “I don’t feel like what I did previously was of much relevance in the rooms where you were negotiating laws, which tended to get very specific about a whole set of issues around ride-sharing.”

The emails in the leak also suggest Plouffe must have known about some of Uber’s more dubious tactics. The files show he was included in correspondence that showed the company seeking to impede investigations or enforcement against its operations, which had been deemed to be illegal in some jurisdictions.

When Uber’s Paris office was raided by France’s competition and consumer regulator, the directorate for competition policy, consumer affairs and fraud control (DGCCRF), in November 2014, Plouffe was copied into an email chain in which senior executives discussed cutting access to staff computers to hide sensitive data, a protocol that later become known as the “kill switch”.

In a response to news of the raid, Plouffe wrote: “They report to [the then French economy minister, Emmanuel] Macron, correct?”

In another case, an email to Plouffe stated the use of the kill switch had probably prevented Uber’s data from being accessed by authorities during a raid. In March 2015, he asked in a message for “real time updates” about another raid in France. Plouffe did not respond to questions about his apparent knowledge of use of the kill switch or why he was included on the emails.

Violence as leverage

The former Obama campaign chief also had some personal experience of how taxi drivers had been stoked up by Uber’s business model. At a breakfast meeting in the Hotel Amigo in Brussels in September 2015, Plouffe, the Brussels region transport minister, Pascal Smet, and another Uber executive were spotted by taxi drivers.

The drivers began hammering on the window. The party had to be shepherded out through a different exit. In another case in Rome, taxi drivers began chasing Plouffe when they discovered he had a meeting with an official, forcing his Uber to drive in reverse down a one-way street.

Such incidents were sometimes seen by executives inside Uber as a useful lever to improve the company’s reputation – something Plouffe seemed to acknowledge. In 2016, in a speech in Cairo, he said: “We’ve seen some violence around the world, but that usually ends up expediting regulatory engagement with the government.”

In a statement, Plouffe said his years at Uber were marked by a “very public, global and sometimes fierce debate about how and whether ride-sharing should be regulated”.

“Sometimes those debates and negotiations were straightforward, sometimes they were more challenging, and sometimes there were people within the company who wanted to go too far,” he said. “I did my best to object when I thought lines would be crossed – sometimes with success, sometimes not.”

Plouffe worked for Uber until January 2017. There are strict rules around lobbying within the US and a month after Plouffe’s departure he was fined $90,000 by the Chicago board of ethics for illegally lobbying the then Chicago mayor, Rahm Emanuel, who had served as Obama’s chief of staff, for Uber.

Useful conversations

If Plouffe was a smooth operator, Messina had a different style. The former Obama campaigner appears to have mingled his consulting work for Uber with his separate political advisory work.

Emails show Messina, who consulted for Uber beginning in 2013, would sometimes check in with the company before planned meetings with his political clients or prospective clients, including Renzi and Rajoy.

In 2015, leaked emails show Messina asked MacGann if he should raise Uber’s regulatory issues in Spain with Rajoy at his first meeting with the then prime minister. When MacGann responded that it would be “helpful” for Messina to tell Rajoy that Uber could bring “precious jobs and tax revenue” to Spain if only someone in his party would “hear us out” – Uber had not “gotten higher” than secretary of state for telecommunications – Messina responded “cool”.

“Not that I think their first meeting with me will lead to a deal, but its useful to start the conversation,” he added.

Rajoy did not respond to a request for comment.

In January 2016, leaked emails show, Messina met Renzi after he had been “briefed in detail” by Uber on Italy’s proposed legislation and Uber’s own preferred amendments to it. “Buck stops with Renzi, it’s make or break for us in the Senate. Let’s see what he comes back with,” MacGann wrote in one email.

A spokesperson for Renzi’s office said the now former prime minister did not believe he ever spoke to Messina about Uber but that if it was ever “touched upon in a conversation” it happened “as a side topic”.

A spokesperson for Messina said his work for Uber involved helping the company “understand the political landscape” in Europe and he had “never engaged in lobbying”. “Further, he never spoke to any head of state on behalf of Uber, including Boris Johnson, Mariano Rajoy, or Matteo Renzi,” the spokesperson said.

Uber did not respond to questions about Plouffe and Messina’s work for the company. It said Messina had not been a consultant since at least 2017.

A spokesperson for Kalanick said that “in an industry where competition had been historically outlawed”, a “change of the status quo” was required. “As a natural and foreseeable result, entrenched industry interests all over the world fought to prevent the much-needed development of the transportation industry.”