OnDecember 18, 2025, Kim Rivers left the White House after President Donald Trump signed an executive order directing U.S. Attorney General Pam Bondi to reschedule marijuana as a less dangerous drug. Sitting at the desk in her hotel room in Washington, D.C., she stared at the thick marker the president gifted her after signing the order.

“Oh, my gosh,” Rivers, the 48-year-old CEO and chairman of Florida-based cannabis giant Trulieve, remembers saying to herself. “I cannot believe that just happened.”

For the last two years, Rivers, along with Boston financier Howard Kessler, and other business leaders and advocates led a lobbying campaign to persuade President Trump—a man who has famously never smoked or had a drink—to reclassify marijuana from a Schedule I substance, the same category as heroin and LSD, to Schedule III, alongside ketamine, steroids and Tylenol with codeine. Since 1970, when President Richard Nixon launched the War on Drugs, marijuana has been banned under federal law. It’s not a done deal, but once the process is complete, it will be the most significant federal drug reform in nearly sixty years.

“The President came to this decision on his own,” says Rivers, at Trulieve’ s Tallahassee headquarters. The pen President Trump gave Rivers, along with a red Make America Great Again hat signed by him—Kim, Great Job —is sitting on a filing cabinet under a plastic case next to her desk. “He believes it’s the best thing for the American people, period.”

Of all the CEOs running companies in the $30 billion (2025 sales) cannabis industry, Rivers, has become the Trump whisperer. Many other executives have long boasted about their proximity to the president, or their lobbying efforts, but it was Rivers who successfully represented the industry and debated nay-sayers—including Speaker of the House Mike Johnson—in the Oval Office about why it’s time for America to end its war on pot, start regulating it and studying its medical uses.

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Part of Rivers’ success is no doubt because she is a well-connected Floridian and a respected, successful CEO. A cofounder of Trulieve, she has grown the company from a single Tallahassee dispensary in 2016 to a cannabis juggernaut that generated $1.2 billion in sales last year with a footprint of nearly 239 stores across eight states, and a 35% market share in Florida’s $2 billion (2025 sales) medical market. Rivers and Trulieve also made large donations to Trump-related political groups, according to data from the Federal Elections Commission, and $750,000 to his inaugural committee. She has attended fundraising events, hired powerful lobbyists, and scored an invitation to the inauguration and had meetings in the Oval Office. Because of that, she has become the most influential executive in the state-regulated marijuana industry, which now spans 40 states with some form of medical sales and 25 with recreational markets.

“I take very seriously the sense of responsibility to represent the industry,” Rivers says. “I’m incredibly grateful and humbled to be able to have a seat at the table and to be a part of such a historic event.”

Florida’s Bradford County Sheriff Gordon Smith, who was also in the Oval Office meeting with Rivers when President Trump made the decision to reschedule marijuana in early December, says that Rivers “had [the president’s] ear.”

“She can bite like a crocodile when need be; she's very sharp with that, but she's smooth with her delivery,” says Smith. “He trusted her.”

Rivers’ relationship with Trump began in 2024 when Trulieve mounted a campaign (along with Smart & Safe Florida) to convince Floridians to vote yes on Amendment 3, a ballot measure to legalize recreational marijuana sales in the state. Trulieve spent around $150 million on the effort. In August of that year, Rivers found herself in Bedminster, New Jersey, meeting Trump, a source with knowledge of the meeting says, about a month after he survived the assassination attempt during a campaign stop in Butler, Pennsylvania. In September, Trump, a Florida resident, wrote on Truth Social that he would be voting “yes” on Amendment 3 and confidently predicted: “As President, we will continue to focus on research to unlock medical uses of marijuana to a schedule 3 drug, and work with Congress to pass common sense laws.”

On Election Day in 2024, Amendment 3 was defeated, which delivered a big blow to Trulieve and every other cannabis operator in the state. But Rivers maintained her relationship with Trump. “When you look at it in those terms, maybe not such a bad deal,” she says, set against a framed portrait of President Abraham Lincoln in a glittery blazer hanging on the wall behind her.

By early December 2025, nearly a year after Trump returned to the White House, Rivers had another meeting with the president, sources with knowledge said. She had the chance to talk with the President, who seemed to be leaning towards issuing an executive order to complete the rescheduling process that President Joe Biden started in 2022.

A week later, and about ten days before Trump signed it, Rivers was in the Oval Office again, this time seated in front of the Resolute Desk and flanked by United States Secretary of Health and Human Services Robert F. Kennedy, Jr., administrator of the Centers for Medicare & Medicaid Services Mehmet Oz, Kessler, Scotts Miracle-Gro CEO Jim Hagedorn and others explaining to the President of the United States that marijuana is in the wrong category.

Trump remarked that he had heard from many people about this issue, including former heavyweight boxing champion and cannabis entrepreneur Mike Tyson. At one point, Trump telephoned Speaker Johnson, who urged the president not to sign the order for moral reasons and to protect American children from the harms of drugs. Trump handed Sheriff Smith the phone, who told Johnson that while he had voted against legalizing medical marijuana in Florida, he had come around to the issue. “My grandfather said there are two people who can’t change their mind—a fool and a dead man. And I don’t want to be either,” Smith said to Johnson. “I found that we better put guardrails in place and control it and regulate it.”

During that meeting, according to multiple sources, Trump had made up his mind and wanted to post it on Truth Social immediately. His staff urged him not to, and Trump then told staffers to start drafting the official executive order in another room.

“I’m not going to be taking it,” President Trump joked during the press conference he held a week later to celebrate the signing. “It’s an honor to do this.”

Born in Jacksonville, Florida, Rivers’ mother was an assistant principal, and her father was a cop with the Jacksonville Sheriff’s Office. She went to Florida State University to study political science and multi-national business—“It kinda worked out,” she jests—and in 2003, she graduated law school at the University of Florida and moved to Atlanta to work as a securities and M&A attorney. Eventually, Rivers moved back to Tallahassee and started her own business, buying up hotel assets, upgrading them and selling the portfolios to hospitality companies.

By 2014, she had made “enough” money and decided to gamble on the nascent cannabis industry. That year, Florida lawmakers legalized a CBD/low THC program, but the state’s first attempt to legalize medical marijuana failed and was gearing up to try again via a ballot measure. Rivers had met Richard May, the son of a plant nursey owner, and Florida businessman John "J.T." Burnette, who was her boyfriend at the time, made an introduction to Thad Beshears, whose family owned another nursery company and is brothers with Burnette’s longtime friend, former Florida state Rep. Halsey Beshears. Rivers, May, a college friend named Jason Pernell and Beshears’ family formed a consortium with a third nursery, Hackney, creating Trulieve. The company won one of five medical marijuana licenses in 2015. (Burnette and Rivers eventually married, but he is not a founder, employee or investor in the business. A construction company he had a minority stake in did build facilities for Trulieve over the years, according to public filings.)

Trulieve opened its first dispensary in a strip mall near the State Capitol in Tallahassee and a 60,000 square foot cultivation facility in a former tomato packing plant in nearby Quincy in 2016. Two years later, the company went public in Canada.

In 2021, Trulieve became one of the country’s largest cannabis companies by purchasing Arizona-based Harvest Health in a $1.4 billion deal, expanding its footprint and revenue. (When the deal was announced, the price was $2.1 billion before stock prices crashed.)

That same year, Burnette was convicted of extortion, bribery and other charges in a scheme unrelated to Trulieve. During trial, it came to light that he had bragged to an undercover FBI agent that he had worked with Rep. Beshears to insert language into legislation that would block competitors from the state’s cannabis industry. In court, Burnette walked back his statement. Neither Beshears, Trulieve or Rivers were implicated in the case. After Burnette's conviction in 2021, Trulieve voiced its continued support for its CEO.

Today, Rivers owns about 10% of the company’s stock, a stake currently worth more than $100 million, even though the stock price dropped 87% over the last five years. Despite Trulieve’s $1.2 billion in annual revenue—the majority of which comes from medical sales—the company posted a $122.2 million net loss last year. Its empire spans nine states and is waiting on its tenth and eleventh in Alabama and Texas, where it has a conditional license in the state’s burgeoning program. While Texas is only allowing low-THC products, Rivers says the market is likely to evolve. (The state has one of the country’s largest hemp market, with an estimated $5 billion in annual sales.)

“A lot of markets are incremental,” says Rivers, noting that Florida’s program launched without smokable products ten years ago and is now the country’s largest medical market. “Texas is going to be similar in that respect.”

As the gate rolls open to Trulieve’s state-of-the-art 80-acre cultivation campus in Monticello, Florida, you can smell the company’s crown jewel long before you can see it. The facility, which has 11 buildings with about one million square feet of space and its own electrical substation, opened in 2022. Inside the largest building, spanning 750,000 square feet, there are 18 flower rooms, one clone room, and three mother plant rooms. Using recycled ground water, it produces tens of thousands of pounds of weed a year, with strain names including Garlic Gas, Sin Mint Sorbet, Khalifa Kush (rapper Wiz Khalifa’s strain), Wedding Crasher and Pineapple Upside Down Cake.

“We call this facility the ‘Megatron,’” says Rivers. “We believe it is the most efficient [cannabis] facility in the United States.”

Rivers has a point. Instead of hand watering each plant, water is piped in from two giant tanks to each potted plant on an automatic timer. And in place of employees who would need to move each plant every 12 hours from total darkness to LED lighting, a mechanical trolley mechanism shuttles plants from light rooms to dark rooms, also on a timer, taking only seven minutes to swap out hundreds of plants at a time. Eventually, Rivers wants to expand the Megatron concept to other states. “This is a testing ground for us,” she says. “As we continue to dial it in, we already have notes in terms of things that we would change in the next iteration of a Megatron.”

Trulieve is the epitome of corporate cannabis, although Rivers is prone to saying “y’all” and “bro” occasionally. She says she modeled it on other companies that have nothing to do with pot, including Starbucks, taking inspiration for Trulieve’s retail experience, and Marriott, for Trulieve’s customer loyalty program.

“Coffee is pretty commoditized,” she notes, “and the fact that [Starbucks] made it a great, consistent quality product, and they're constantly innovating, constantly adding new lines or new reasons for you to come in.”

While rescheduling cannabis won’t give consumers a new reason to sample Trulieve’s products, it will be a boon to the company during tax season. Cannabis companies are required to file under a punitive tax code—280e—that was created for drug traffickers of any Schedule I or II substance. The code only allows for one deduction, cost of goods sold, and can have an effective tax rate of 60% of gross revenue or higher. A couple of years ago, Trulieve developed its own theory about why 280e does not apply to its business and filed amended tax returns in 2023 for prior years explaining they were due a refund. The IRS then sent Trulieve multiple checks, totaling $114 million, and the company has since been taking normal business deductions. (Most of the major cannabis operators, including Curaleaf and Green Thumb Industries, no longer pay under 280e, arguing their own theories.)

It is calculated, but still a huge financial risk. In its public filings, Trulieve has identified an uncertain tax liability of $670 million, most of it due to not paying under 280e, which Rivers explains is the “worst case scenario” if the IRS rejects its thesis.

“We do not believe that from a medical marijuana perspective that we are drug traffickers,” says Rivers. “We're operating under a state licensed program within the confines of a state program.”

As 280e does not apply to Schedule III drugs, rescheduling would deliver a huge financial win for Trulieve and its peers. That net loss of $122 million last year? If marijuana is categorized as Schedule III, it will be an “overnight flip” to profitability.

“We will be pretty immediately net income positive,” she says.

As Rivers walks through the Megatron in black Jimmy Choo high heels—despite a calf injury she got on the pickle ball court a few days ago—she passes rooms filled with small jungles of pot plants and answers a question about how it felt these past few years to have been considered a drug trafficker under federal law.

“First of all, I prefer ‘drug lord-ess’,” she jokes, before getting serious.

Rescheduling will not make marijuana federally legal, but it is a sign that the incremental change that has unfolded across the U.S. since California legalized medical marijuana in 1996 and spread across 40 states has started to change how the U.S. government deals with marijuana. And eventually, says Rivers, marijuana will be legal under federal law.

“The laws are going to change,” she says. “Momentum has been building. This has really been decades in the making.”

While legalization has historically been a strong issue for Democrats, it has taken two presidents—a Democrat, Joe Biden, and a Republican, Donald Trump—to make rescheduling possible. Rivers, who can play both sides of the aisle as well as anyone, says that’s because marijuana is not a red or blue issue.

“At its core, it’s really about personal freedom,” Rivers says. “It's about wellness, it's about adults being able to take control of what they're putting into their bodies that makes them feel better in many cases. And so that's universal. That's not anything to do with politics.”

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