David Panton, left, with Ted Cruz while they were students at Princeton University. (Daedre Levine)

— The ambitious young men sat for hours at a restaurant here to map out plans for a business venture that could make them millions.

In a group that included three Jamaican entrepreneurs, one participant seemed out of place — a 27-year-old former U.S. Supreme Court law clerk of Cuban descent who was visiting from Washington.

Ted Cruz had been invited by his roommate from Princeton and Harvard Law, David Panton, who was eager for the group to win the rights to manage a new Caribbean-focused investment enterprise launched by one of the island’s most prominent executives.

The idea was modeled after U.S. private equity companies that made fortunes by using investor dollars to remake underperforming companies. The Caribbean concept came with a twist — the investor dollars would be drawn in part from governments, including from the United States, leveraging funds intended to boost the developing world.

It was an odd fit for Cruz, who as early as high school and college expressed a strong belief in limited government. But the plan held potential for big profits. And Cruz was welcomed by Panton’s fellow Jamaican partners as a skilled negotiator well suited to help hone their pitch for managing the new firm.

“A good devil’s advocate,” said Jeffrey Hall, one of the partners at the meeting.

With Cruz’s help, they won the right to control what they hoped would be a $150 million fund. The firm, founded in 1998, lost its contract within five years, in part because of a dispute over an investment decision, and was soon shuttered.

Nevertheless, it provided a tidy sum for Cruz. He initially pitched in $6,000 for start-up costs and exited the partnership shortly before it disintegrated with a payout of $25,000, plus a promise of an additional $75,000 to come later, according to Panton.

The episode is one part of an unusual chapter in Cruz’s life — a foray into Jamaican society and politics amid his otherwise straightforward rise from the Ivy League to coveted clerkships to the U.S. Senate and, now, the top tier of the Republican presidential field.

Ted and David

At the heart of it all was Cruz’s long and enduring bond with Panton. The two college buddies had each been destined for high-profile success, the Canadian-born Cruz as a constitutional lawyer in the United States and Panton, son of prominent Jamaican parents, as a potential prime minister of his native country.

When their business dissolved in 2003, Panton seemed to stumble — through a very public divorce from a former Miss World and a romance with a former Miss Universe that provided tabloid fodder across the Caribbean. Panton has said that Cruz provided emotional support through some of those difficult times.

Cruz’s loyalty over many years to Panton, who he has said is “like a brother,” shows a different side of a politician who has developed a reputation for being abrasive, even unlikable. Panton, in turn, has been one of Cruz’s most enthusiastic political supporters, helping launch the first super PAC backing the senator’s White House bid.

Cruz declined to be interviewed for this article, and a campaign spokesman did not respond to detailed written questions. Panton agreed to answer questions only via email.

Panton and Cruz during college. (Daedre Levine)

The two were teenagers when they first met, assigned to live in the same freshman dorm at Princeton. They were an “unlikely couple,” Panton said last year to a radio station in Atlanta, where he now lives. Cruz was a deeply conservative Hispanic from a poor background while Panton, who is black, hailed from the upper crust of Jamaican society, where his father ran one of the island’s largest companies.

“Coming from a small school in a small town in Jamaica, I was young and felt both academically and culturally overwhelmed,” Panton told The Washington Post. “Ted was extremely pleasant and friendly and expressed genuine interest in my background.”

Cruz and Panton shared the love of a good argument and decided together to join Princeton’s competitive debate team, he said. Some classmates were baffled by the relationship between two people with seemingly opposite personalities. Panton, with his lilting Jamaican accent, exuded charm and made friends easily. Cruz was combative, developed few friendships and earned some lifelong enemies.

“You either didn’t know Ted Cruz, you hated him, or you were David Panton,” said Craig Mazin, who was Cruz’s freshman-year roommate before Cruz left midyear to room with Panton. Mazin has been vocal about his dislike of Cruz.

Panton said that over movies, video games and basketball, he saw another side of Cruz. “I am always surprised and perplexed by those who said they did not like Ted,” he said.

Panton’s Jamaican home played an important role in the relationship. Panton invited Cruz and Adam Erlich, a friend and fellow debater, to visit his family on the island and get a behind-the-scenes tour of Jamaica’s most powerful institutions, Erlich said.

They visited the local stock exchange and the newsroom of the island’s largest newspaper, he recalled. They also attended a raucous political rally for the Jamaica Labour Party, the more conservative of the island’s two major political parties.

As the rally began, Erlich recalled that he and Cruz watched in awe as their friend chatted amiably with Edward Seaga, who led the JLP for decades and had served as Jamaica’s prime minister.

“People thought Dave was going to be the prime minister of Jamaica and Ted would be an excellent constitutional lawyer,” said Stephen Wunker, a Princeton debate teammate.

In Jamaica, Seaga shared that view, saying in an interview that he viewed Panton as a possible successor and knew Cruz as Panton’s good friend who could make a brilliant argument.

“I thought David would be an excellent political leader,” Seaga said last week in his office at the University of the West Indies, surrounded by photographs of him and other world leaders.

Cruz and Panton remained roommates at Harvard Law School, until Panton left for a Rhodes scholarship at Oxford University.

Panton returned to Harvard shortly after Cruz graduated and was elected to lead the Harvard Law Review, becoming the second black person — after Barack Obama — to hold the position. When Panton was elected to the post, he later told a Jamaican newspaper, his first call was not to his parents but to Cruz, then clerking for a federal judge in Virginia.

At the time, Panton and Hall, a Jamaican friend also at Harvard, began discussing the possibilities of a Caribbean private equity fund.

A similar idea was being explored in Jamaica by a prominent insurance executive, Dennis Lalor, who envisioned stimulating the region’s economy by luring investment largely from development banks funded by area governments.

Panton, Cruz and their partners, believing a regional private equity firm could turn big profits, wanted in.

After their strategy session, they successfully won the management contract from Lalor. Over a long lunch on the veranda of Lalor’s country estate in Jamaica’s famed Blue Mountains, the partners and the executive looked with optimism at the future — and probably did not foresee the bitter falling out that would come later.

Cruz a passive investor

Cruz was “extremely helpful” in persuading Lalor to bring the young company aboard, Panton said, calling Cruz the “smartest, most strategic and most persuasive person I know.”

Cruz’s initial investment amounted to a 10 percent stake in the new company, according to corporate records filed in Jamaica. After its founding, he was a passive investor, according to Panton, playing no role in running the company.

The other partners zipped back and forth to bank headquarters and elsewhere seeking funding and then all over the Caribbean in search of places to invest it.

They soon bought stakes in a regional liquefied-natural-gas company, a coffee distributor and a Kingston restaurant.

In 1999, the partners took a gamble that would later haunt them — buying a large stake in a decades-old Kingston metal production company struggling for survival as cheaper goods from China flooded the Jamaican market.

The partners attempted to fix the problems by selling off the metal company’s old-line manufacturing and retail operations.

Eventually, little was left but the company’s land and buildings, which the partners hoped to sell for a profit. About 400 Jamaicans lost their jobs in the years after the equity firm bought the company, said Neville Scott, who had been the metal company’s chief financial officer.

Panton said the transaction was profitable, many workers were rehired by new owners and all received severance pay.

As the business grew, the partners began to focus on other aspects of their personal and public lives.

Panton was appointed by Seaga to a seat in Jamaica’s unelected Senate. Panton also earned headlines at home in 1999 for his marriage to Lisa Hanna, a scion of another top Jamaican family who had become a local celebrity after winning the Miss Jamaica pageant and then being named Miss World.

Cruz gave a toast at the couple’s wedding reception at a Manhattan restaurant, earning laughs as he gently roasted his friend.

Panton returned the favor as best man at Cruz’s 2001 California wedding to Heidi Nelson, whom Cruz had met while serving as a domestic policy adviser for George W. Bush’s presidential campaign.

After the election, Cruz took jobs in the Bush administration, but he retained ties to the Jamaican world of his friend Panton.

On a visit to Jamaica in 2001, Panton arranged for Cruz to serve as the guest speaker at a meeting of Generation 2000, a wing of the JLP political organization Panton had helped found for young professionals.

A 2001 edition of the Jamaica Gleaner shows Panton and Cruz with political leader Edward Seaga, left. (Rosalind Helderman/The Washington Post)

In an article headlined “Tips from strategist for JLP,” the Jamaica Gleaner, the country’s largest newspaper, described how Cruz counseled the party to adopt American campaign innovations, such as the use of political consultants and intense message discipline, to win a political majority.

“Anytime you’re communicating with the public in the political arena, you should have a message, and you should be focused on that message,” Cruz told the group, according to the paper.

As an example, Cruz said that if asked “Are you a criminal?” that a politician should avoid the response “I am not a criminal,” an answer that would make for a good headline. The politician should instead answer, simply, “No,” Cruz advised.

Around the same time, Cruz attended the Kingston christening of Panton’s first son, where he and his Jamaican business partners were all named godfathers of the boy.

Hall, one of the four business partners, recalled that Cruz was particularly concerned that the day go well for his friend.

“We were very aware of the need to conduct ourselves as grown-ups,” Hall said. “He was the one saying: ‘You must be clean shaven. You must be on time.’ ”

After the church service, Cruz and his business partners concluded the day with an intensely competitive game of Monopoly, Hall said.

But problems were starting to emerge for the company.

‘Integrity 101’

According to Lalor and two of his business associates, the partners were having trouble finding companies in the region with strong-enough financial controls to handle a large infusion of outside capital.

What’s more, Lalor said he was upset when he was not consulted in advance of the purchase of the metal-products company. He said the four partners, in their initial pitch, had promised to be transparent in their dealings.

“That was shocking,” Lalor said. “It was the morality of it. The next thing I knew it was on our books. . . . It was Integrity 101.”

Panton said Lalor’s allegation about the metal company investment was “surprising to me.” He said the investment was made “entirely appropriately” and called Lalor’s complaints about a lack of consultation “disingenuous.” Panton said he and his partners operated their company with the “highest levels of integrity,” that it had a strong record of investment and that Lalor’s complaints were “insincere, false and unacceptable.”

In 2002, Panton moved to buy out his three partners, including Cruz. Panton said he believed the company’s position would be improved by having one owner. Panton added that Cruz wanted to divest because his wife, Heidi, had taken a job at the Treasury Department with oversight of international trade.

For Cruz’s 10 percent share in the company, Panton agreed to pay $25,000 immediately with an IOU for $75,000. Panton said Cruz received no other income from the company.

The promissory note would later bedevil Cruz when Time magazine, which first reported some aspects of his Caribbean investment, revealed in 2013 that he had failed to include the asset on two years of Senate ethics forms. Cruz said it was an oversight and amended the forms. Cruz has never cashed in the note, but Panton has said he stands ready to pay if asked.

Lalor, who said Panton’s sole ownership violated the original terms of the company’s contract, moved to sever it immediately.

The end of the contract was a blow to Panton’s company. Without the contract, the annual guaranteed management fees and the potential for a high share of profits disappeared.

Panton described the resolution as a “win-win,” saying Lalor bought him out while the company was on an upswing, clearing the way for him to return to the United States. He said he remains proud of what he and Cruz accomplished in a few short years.

“Ted invested in a start-up company with zero revenue and zero profits, with ambitious plans to do something that no one else had done before,” Panton wrote.

Panton took a job at a $1.4 billion private equity firm in Atlanta in 2004, not long after Cruz was appointed solicitor general of Texas, a job in which he would draw notice from conservative leaders.

Panton said he and partners bought the Atlanta-based firm three years later. He became an adjunct professor at Emory University’s business school, joined the board of an Episcopal school and became chairman of the Jamaica Chamber of Commerce of Atlanta.

But Panton’s personal life was rocky. After Panton’s marriage ended, Cruz offered his support during a painful and very public custody battle, Panton said. “As a good friend, Ted has always been kind, thoughtful and caring,” Panton said.

When he won custody of his son in Atlanta, Panton said, the first trip he took with the boy was to Texas to see “Uncle Ted” and Heidi.

As Cruz has risen, Panton has been there to cheer him on.

He gave the legal maximum donation of $5,000 to Cruz’s 2012 U.S. Senate campaign. And on the night of Cruz’s election, Panton stood on the stage just behind him.

Ted Cruz holds his daughter Catherine after winning a runoff election for the GOP nomination for a U.S. Senate seat from Texas in July 2012. Panton is behind him to the left. (Johnny Hanson/Houston Chronicle via AP)

When Cruz began to contemplate a presidential run, Panton was again a visible presence, helping to launch a pro-Cruz super PAC called Stand for Principle.

Organizers initially predicted the PAC would raise $50­ million, pointing to Panton’s role as evidence of the group’s seriousness. That never happened; the organization was eclipsed by a collection of other super PACs that have raised tens of millions of dollars to bolster Cruz’s campaign.

Federal Election Commission records show that Panton wrote a check for $100,000 in November 2014 to his PAC — about a third of the group’s overall proceeds.

In early 2015, Panton’s father became ill with cancer. Like Cruz’s father, Keith Panton was a pastor, and Cruz and the senior Panton had become close.

On Feb. 18, a day when Cruz participated in a news conference warning the Obama administration not to proceed with its immigration plans, Cruz and his wife took time to call the hospital room where the senior Panton lay dying.

“I will never forget my father’s reaction when I told him that Ted wanted to talk to him,” Panton recalled. “Frail and weak, his eyes grew wide and he beamed as I gave him the telephone.”

“It was sadly the very last time I saw my father smile,” Panton said.

Franklin McKnight in Kingston and Alice Crites in Washington contributed to this report.