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As pot prohibitions tumble state by state, companies are in a race across America for licenses and locations. The best funded of these cannabis contenders, Curaleaf Holdings, is a creation of Russian billionaires.

Curaleaf’s board chairman Boris Jordan, 52, played central roles in Russia’s messy return to capitalism in the 1990s. He helped arrange its first privatization, launched its first investment bank, and dove into the scrum to snatch up Russian assets—with mixed results for some backers like George Soros. Jordan’s bid for a pot empire is a return to the spotlight for the Moscow-based investor, who lowered his profile after attacks from all sides as chief of the Russian independent television network NTV, before the Kremlin muzzled it in 2003.

Backing Jordan’s marijuana ambitions is Andrei Blokh, who got rich on Russia’s oil resources with oligarch Roman Abramovich (best known recently as the owner of luxurious superyachts and the Chelsea Football Club), before bundling up Russia’s dairy industry and selling the conglomerate Unimilk to Danone (ticker: DANOY) in 2010.

“I haven’t been as excited about an industry since 1992, when I came and saw what was going on in the ex-Soviet Union,” Jordan told Barron’s.

His enthusiasm is understandable. Jordan and Blokh together are more than a billion dollars richer than they were a month ago, thanks to Curaleaf’s (CURA.Canada) Oct. 29 debut on Toronto’s Canadian Securities Exchange. At a recent share price equivalent to $5.20 (C$6.90), the stock values Curaleaf at $2.8 billion. Blokh’s 25% stake is worth $660 million, and Jordan’s 28% more than $740 million—and probably more, since Jordan owns supervoting shares that ensure his control.

Just before Wakefield, Mass.–based Curaleaf’s listing, it raised $400 million in a private placement that was the cannabis industry’s largest stock offering ever. It now has deep pockets to bid for U.S. cannabis assets against other multistate chains, which include MedMen Enterprises (MMEN.Canada), Green Thumb Industries (GTII.Canada), iAnthus Capital (IAN.Canada), and Acreage Holdings (ACRG.U.Canada). These U.S. outfits have all listed on the Canadian Stock Exchange—sometimes jokingly referred to as the Cannabis Securities Exchange—because the New York Stock Exchange and Nasdaq remain wary of pot’s federal illegality here. (Read a cautionary tale on the investment risks of marijuana stocks.)

Shares in Canada’s pot producers rose sharply in anticipation of that country’s nationwide legalization last month. Although they’ve retreated a bit recently, leaders like Canopy Growth (CGC), Aurora Cannabis (ACB), Aphria (APHA), Tilray (TLRY), and Cronos Group (CRON) still trade for upward of 90 times their annualized revenues.

Shares of their U.S. counterparts are catching up fast, as more states approve sales. Earlier this month, Michigan voters made their state the 10th to approve recreational sales, while Missouri and Utah joined 31 others in allowing prescription sales. Massachusetts will soon launch recreational sales, and the governors of New York, New Jersey, and Illinois want to legalize recreational use in their states.

“It’s going to go like a domino effect,” Jordan said. “You’ll have half the population with access to adult-use cannabis.”

Pot’s legalization is a terrific business opportunity, with U.S. winners sharing a market that could surpass $50 billion in annual sales. Curaleaf’s boss scoffs that Canadian cannabis companies have “astronomical valuations,” but says Curaleaf’s own share price is “perfectly reasonable.” U.S. operators trade at lower multiples, he says, and are pursuing a market with nearly 10 times the population of Canada.

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At $2.8 billion, Curaleaf’s valuation is 40 times the annualized revenues of its cannabis dispensaries in the last-reported June quarter. It lost money on the quarter. But Jordan said his company just turned cash-flow positive and will generate $100 million in free cash flow next year, on revenue of more than $400 million.

“We’re opening a dispensary a week,” Jordan says. Curaleaf aims to expand its footprint from 33 stores across 10 states, to 41 stores by year-end 2018, then almost 70 stores and 12 states by year-end 2019.

The promoters of America’s biggest pot stock made their money amid the chaos of Russia’s privatizations, and Jordan’s financial history there had wild ups and downs that could deter some Curaleaf investors. While still in his 20s, the U.S.-born Jordan went to Moscow in 1992 as a Credit Suisse banker and helped privatize the first state-owned enterprises. He then co-founded a Russian investment bank called Renaissance Capital that recruited investors like Soros and the Harvard University endowment in the takeover of Russian oil, telecom, and timber resources.

Initial gains were crushed in the 1998 crisis triggered by Russia’s debt default. “Being the highest profile international banker in Russia at the time, that had a lasting impact,” recalls Jordan. “I was telling the world to invest in Russia, so that reflected very, very badly on me.” Renaissance split up, with Jordan taking charge of its investment vehicles, the Sputnik Funds.

One of Jordan’s investment ideas was the telecom company Svyazinvest. Soros later wrote that the nearly $1 billion that his Quantum fund invested in Svyazinvest was the worst investment of his career. Another Sputnik wager, on the National Timber Company, didn’t work out, either, a former fund investor told Barron’s. The timber investment led to a small loss, says Jordan, amid a global downturn in timber prices. Soros chose to bail out of Svyazinvest at a loss, Jordan says, but Jordan held on for nine years and made a profit. “The Soros fund’s decision to get in and to get out of Svyazinvest was theirs alone,” says Jordan.

Then, rival groups of oligarchs fought in the courts and on newspaper pages for control of Sidanco, an oil giant chaired by Jordan. Sidanco also figures prominently in Red Notice, the memoir of Bill Browder, the Russia investor turned human-rights activist, who says his first success in fighting abuses in Russian business was stopping an attempt by Jordan to disenfranchise Sidanco’s minority investors.

Browder, says Jordan, was no hero. “Bill never wanted to invest in the company,” Jordan says. “He tried to greenmail Sidanco.” Browder says that characterization is untrue.

In any case, Jordan says Sputnik investors ultimately made three times their money in Sidanco. An even bigger success was data-center firm TelicityGroup, a tech investment he says earned Sputnik 15 times its investment by 2007. By Jordan’s accounting, he has averaged a better-than-35% annual rate of return on Sputnik’s investments since 1998. Today, Jordan’s most valuable holdings are a Russian insurance company and Curaleaf. These have gained him a nice lifestyle, split between Moscow and Miami Beach, where he recently sold a penthouse for $26 million.

Like Jordan, Blokh is a U.S. citizen who struck it rich in the collapse of the Soviet Union. A friend since youth of Abramovich, Blokh became president of Sibneft—the oil company Abramovich got in Russia’s privatization and sold for more than $13 billion. Blokh’s dairy conglomerate was peeled off from Abramovich’s food holdings. Blokh declined to comment.

He isn’t the only Abramovich associate behind Curaleaf. Before adopting the name Curaleaf, Jordan’s cannabis venture called itself PalliaTech. And PalliaTech’s Florida incorporation filings listed as a director Anna Evdokimova, a top investment executive at Abramovich’s asset-management firm Millhouse. She was Blokh’s representative, says Jordan.

Abramovich was listed in January by the U.S. Treasury Department among the oligarchs close to Vladimir Putin and potentially subject to property ownership sanctions. The United Kingdom refused to renew the oligarch’s visa this year, after enacting rules concerning residents with unexplained wealth. In any event, Jordan says that Abramovich’s Millhouse is not a Curaleaf investor.

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Curaleaf’s Russian roots may be fascinating history, but they don’t diminish the size of the U.S. cannabis opportunity or the cash the company raised from over 100 institutions and wealthy individuals around the world. On the roadshow, nobody asked about Russia, says Curaleaf.

“I’m very proud of my track record, particularly in Russia,” Jordan says. “I got to do an emerging market in the 1990s. I got to do technology in the early 2000s. And now I get to do this. I consider myself very lucky.”

Corrections and Amplifications

An earlier version of this story mischaracterized the Harvard University endowment’s experience with Boris Jordan’s fund. In addition, Jordan says the Soros fund’s losses resulted from its own decisions, not Jordan’s.

Write to Bill Alpert at william.alpert@barrons.com