Ten weeks before the collapse of Lehman Brothers Holdings Inc., a financial disaster that ushered in the global economic crisis in September 2008, Jeb Bush was in Mexico City to seek help from billionaire Carlos Slim.
Mr. Bush signed on with Lehman after leaving the Florida governor’s mansion, making it clear he wanted work as a hands-on investment banker rather than hold a ceremonial role typically given ex-politicians. Now was his chance.
Mr. Bush was a longtime acquaintance of Mr. Slim, at the time ranked as the world’s second wealthiest individual and one of several deep-pocketed investors on Lehman’s radar. “Project Verde” was supposed to bring home badly needed cash and confidence. Mr. Slim, however, was more interested in talking baseball than investing in the troubled firm.
More doors closed that summer before Lehman shut its own, but Mr. Bush, following in the footsteps of a grandfather and great-grandfather, latched onto investment banking through the worst downturn since the Great Depression.
For more than seven years, nearly the length of his two gubernatorial terms, Mr. Bush, a candidate for the Republican presidential nomination, spent as much as half of his working hours advising Lehman and later Barclays, which bought the collapsed investment bank’s U.S. business. He wasn’t an employee of the firms, said people familiar with the matter, but was paid to attend meetings, dinners and conferences where he spoke to clients and bank executives on such subjects as health care, education, immigration and energy—matters he has started taking up this year with voters.
Mr. Bush earned about $1.3 million a year at Lehman and some $2 million from Barclays, his campaign said.
Bankers and trading executives described Mr. Bush’s contributions as “rich in content,” which on Wall Street translates to having the kind of timely expertise that clients expect from top firms on topics essential to their investments.
“I spent a lot of time, I probably spent about 40% of my time working for Barclays,” Mr. Bush told reporters in June. “I did a lot of their conferences where I spoke and I interacted with their clients.”
Mr. Bush received a warm welcome on Wall Street, where financial firms often seek former political figures to help open doors. At least six firms offered Mr. Bush a position when he finished his second term as governor in January 2007, according to people familiar with the matter.
When he joined Lehman in June that year, Mr. Bush was the brother of a sitting U.S. president, George W. Bush, and already had ties with the investment bank, known for its scrappy culture and aggressive management team led by chief executive Richard Fuld, a longtime Democrat.
Mr. Bush would spend most of his time at Lehman working under Steve Lessing, who had been a “Ranger” for George W. Bush, a title for supporters who raised at least $200,000 for Mr. Bush’s 2004 presidential campaign. Mr. Lessing headed client-relationship management and was the face of the firm to many money managers, hedge funds and insurance companies.
Mr. Bush soon drew the attention of Lehman’s senior investment bankers, who looked for ways to put him in front of clients. He appeared at conferences for health-care clients and corporate directors, and joined a ski junket for bankers, people familiar with the matter said. He crisscrossed the country and flew commercial, often alone.
In late 2007, Lehman executives who spotted him striding past in midtown Manhattan— BlackBerry pressed to his ear—said they recalled thinking that Mr. Bush, in a matter of months, had completed his transition from governor to harried bank executive. “This guy is the brother of the president, just walking by himself, no security,” a former Lehman manager said.
Mr. Bush said he spent most of his time at Lehman “dealing with their customer base, providing insights in things like the madness of Washington, D.C.”
More than a dozen of Mr. Bush’s former colleagues and clients described him as focused, blunt and often opinionated. Unlike most former politicians in finance, Mr. Bush was seen as “commercial,” almost a term of endearment on Wall Street meaning he understood how bankers prepared for meetings, advised clients and made money. He frequently reminded clients he was part of a team and ended meetings with a “thank you for letting us work for you,” or a direct appeal to hire the bank, recalled one former Barclays banker.
Mr. Bush’s banking experience is unusual for a presidential candidate, said Barbara Perry, director of presidential studies at the University of Virginia’s Miller Center. More common backgrounds are in law, politics or the U.S. military. Finance, however, is part of the Bush family history. Jeb’s great-grandfather, George Herbert Walker, and grandfather, Prescott Bush, both worked at the firm that became investment bank Brown Brothers Harriman & Co.
“I’d say for the Kennedys, politics was in their DNA,” Ms. Perry said. “In the case of the Bushes, it’s both politics and high finance.”
Ohio’s Republican Gov. John Kasich, another candidate for the GOP nomination, also worked as a managing director at Lehman in the eight years leading up its 2008 demise.
Mr. Bush’s Wall Street work could play well with many traditional Republican voters. It also could be a lightning rod for criticism.
Mitt Romney, the GOP presidential nominee in 2012, was pilloried by some of his Republican primary competitors, as well as President Barack Obama’s campaigners, for his longtime work as a private-equity executive.
“If 2012 taught us anything, it is that you have to be well-prepared to tell your story about your business experience in a proactive way before your opponents frame it negatively around your neck as an albatross with voters,” said Kevin Madden, a top aide to Mr. Romney during his 2008 election bid.
Mr. Bush has previously taken a softer line toward the financial sector than his campaign rivals, particularly Sens. Rand Paul and Ted Cruz, who are also seeking the Republican nomination.
Earlier this year, a political-action committee that has endorsed Mr. Paul launched an ad campaign dubbed “Bailout Bush.” The group criticized Mr. Bush for, among other things, his stints at Lehman and Barclays, as well as his past endorsement of government support for banks during the crisis.
At a November 2013 event for a Wall Street trade group, Mr. Bush said banks have been unfairly maligned. Privately, he has voiced issues with the landmark Dodd-Frank bill to overhaul financial regulations after the crisis.
“If you listen to most of the media, the banks and the financial industries in general are bad, and they should be shrunk or taken apart,” Mr. Bush said at the 2013 gathering, adding that a “strong banking sector is essential to provide the capital that fuels economic growth.”
He also said that banks, “while having made some terrible and costly decisions in the past, are now doing business in a much more responsible way.”
Mr. Bush’s contracts with Lehman and Barclays stipulated the firms wouldn’t ask him to lobby Washington, people familiar with the matter said. As Barclays and other banks scrambled to influence the wave of new rules in the wake of the financial crisis, former colleagues said, Mr. Bush stayed out of it.
Around the time of his 2008 Mexico City trip, Mr. Bush was on the board of a Lehman fund pursuing investments in toll roads and other public works. His successor, Florida Gov. Charlie Crist, in the months after Mr. Bush left office, had signed a bill allowing the state to lease some toll roads, including a stretch of interstate 75, known as Alligator Alley.
Mr. Bush studied documents and advised Lehman executives on the deal, as well as the state’s political pitfalls, according to people familiar with the discussions. Mr. Bush brought lots of energy and “creative problem-solving skills” to Lehman, said Emil Henry, a former executive with the firm who has been active in GOP politics.
By August 2008, Lehman had joined a consortium that was among six bidders on the project. The firm collapsed the following month and Barclays, a U.K.-based lender, bought its U.S. operations following a bankruptcy filing.
Lehman’s fall
Mr. Bush said he wasn’t consulted about Lehman’s difficulties as it veered toward bankruptcy, according to congressional testimony and people familiar with the matter. During a 2012 U.S. House committee hearing, he said no one asked him to intervene on behalf of the firm. Mr. Bush said Mr. Fuld, Lehman’s chief executive, “didn’t ask me to do anything, and I didn’t do anything.”
Mr. Fuld had weighed asking Mr. Bush to call his brother, the president, and raised the idea to some of his executives, people familiar with the matter said. They urged their boss against it, arguing it would put the Bush brothers in an awkward position, the people said, and they doubted it would help.
After Lehman’s collapse, Mr. Bush followed Mr. Lessing to Barclays as a senior adviser, a post he kept until stepping down in December 2014 to weigh a presidential run. The request to keep Mr. Bush after the takeover was blessed by Robert Diamond, then Barclays’s chief executive and a Massachusetts native who had been a fundraiser for John McCain’s 2008 campaign, people familiar with the matter said.
Executives at insurer MetLife Inc. came to view Mr. Bush as part of Barclays’ “coverage team,” the bankers who would regularly call on the insurance company’s leaders, according to people familiar with the matter.
While at Barclays, Mr. Bush also became a trusted adviser to Cigna Inc. Chief Executive David Cordani, people familiar with the matter said.
“Our discussions with key leaders, including Jeb Bush, enable us to understand the perspectives of key thought leaders and share our ideas,” said a spokesman at Cigna, a Bloomfield, Conn., health insurer.
The Affordable Care Act has helped draw Cigna and other managed-care companies into a merger frenzy to save costs and expand market share. Last month, Cigna agreed to sell itself to rival Anthem Inc.
Mr. Lessing said Mr. Bush “added unquestionable value to our clients over the years, and we are delighted they were able to benefit from his time as a senior adviser with us.”
“It wasn’t the Barclays view, it was the Jeb view, about how the world works and it seems to have been quite effective,” Mr. Bush said during the June news briefing. “The amount of time I spent traveling the world talking to their top clients was an indication that I did add value for the enterprise.”
Mr. Bush’s life on Wall Street marked a return to finance. After graduating from the University of Texas in 1974, he took a job at Texas Commerce Bank, a lender founded by the family of James Baker III, who later held cabinet posts in the administration of Mr. Bush’s father, former President George H.W. Bush.
Jeb Bush had joined the bank’s international division, where he worked on analyzing sovereign risks. While based in Caracas, Venezuela, he was frequently on the road to meet clients, extending the banks’ reach to Colombia, Peru, Ecuador, Bolivia and Chile. He took a leave of absence in 1980 to work on his father’s campaign and never returned.
Mr. Bush’s fluency in Spanish and extensive experience in Latin America made him a good choice for the July 2, 2008, trip to Mexico City. He also knew Mr. Slim well: the Mexican billionaire had lent a collection of small-scale Rodin sculptures for the Florida governor’s mansion when Mr. Bush lived there.
Lehman was canvassing a number of rival banks and financial companies in the wake of Bear Stearns Cos.’s near-collapse and rescue by J.P. Morgan Chase & Co. earlier that year.
The trip also gave Mr. Bush a chance to accompany Arizona’s Sen. McCain, the Republican presidential candidate, for part of a campaign swing to Latin America. On July 3, Mr. Bush joined Mr. McCain and his wife for a tour of the Basilica of Our Lady of Guadalupe.
Mr. Bush and a handful of Lehman advisers also met with Mr. Slim in his office that day to propose a number of deals, including an investment in Lehman. The answer, the Lehman team soon learned, was no.
“Project verde was unsuccessful,” Mr. Bush wrote to a colleague after the meeting in a July 5, 2008 email made public during Lehman’s bankruptcy proceedings. “He did not express interest in jv or stock purchase.”
About two months later, on the Monday that Lehman filed for bankruptcy, Mr. Bush was in Florida alongside Mr. McCain.
At a campaign stop in Jacksonville, Mr. McCain railed against the Bush administration’s failure to regulate Wall Street and said taxpayers shouldn’t pay for Lehman’s bailout. “I promise you we will never put America in this position again,” Mr. McCain told voters. “We will clean up Wall Street.”
Write to Justin Baer at justin.baer@wsj.com
