For legalization advocates, the scariest thing about the Republican party this year may not be Donald Trump. It’s the specter of 82-year-old billionaire and ardent prohibitionist Sheldon Adelson slinging vast sums into the coffers of both the Trump campaign and state anti-legalization efforts.

Alarm bells in the cannabis world began ringing last week, when Republican National Convention officials begged Adelson to step in as their last-minute sugar daddy. In a letter obtained by Politico, the Cleveland 2016 Host Committee informed Adelman that previously committed sponsors — including FedEx, Visa, Pepsi, and Coca-Cola — had pulled out because Trump would be the nominee. Adelson’s help, the host committee wrote, would “ensure our Republican nominee has the best possible platform to lay out his conservative case for our nation.” 

It’s unclear whether Adelson responded to the letter. At the very least, he contributed enough to merit a suite in Quicken Loans Arena, which gave him the opportunity to excommunicate Ted Cruz last night after Cruz refused to endorse Trump: 

Having a staunch prohibitionist underwrite the Republican Party’s party, and thereby amass influence over the party’s nominee, policies, and direction, does not bode well for legalization advocates. Especially if Adelson combines support for Trump with financial backing for prohibitionists battling legalization efforts in Florida, Nevada, Massachusetts, Arizona, Maine, and California. For legalization advocates raising money for state initiatives, the landscape of sources in 2016 is far more challenging than it was in 2012. Consider:

How can Adelson’s efforts be anticipated and countered? For clues we can look at anti-legalization campaigns he’s supported in the past, whom he’s giving to this year, and where his staunch prohibitionist attitude seems to come from. 

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A Walking, Talking, Million-Dollar-Donating Contradiction 

The New York Times characterized Adelson, whose net worth has been estimated at $27 billion, as the “combative, litigious owner” of Las Vegas’ Sands Casino, a political kingmaker, a generous backer of local and national politicians, and someone who funds issues he feels strongly about. 

He’s a pro-choice social liberal, a Republican who used to be a Democrat but switched parties in 2012 (and explained the move in a Wall Street Journal op-ed titled “I Didn’t Leave the Democrats. They Left Me.”) According to Florida’s Sunshine State News, Adelson is a close friend of Harry Reid, the Nevada senator and Senate Democratic leader. Reid has said Adelson “lets his stomach and his heart do his thinking for him. He does what he thinks and feels is right for himself and his friends. He’s got a very strong moral and ethical streak.” 

At times, Adelson has seemed to advocate against his own self-interest. Though he amassed his fortune through casino gambling, he publicly rails against internet gambling. Adelson argues that casino gambling is strictly regulated, but it’s nearly impossible to determine whether online gamblers are underage or fueling a destructive addiction. Of course, an alternative explanation is that Adelson could simply be working to undermine his competitors.

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When it comes to cannabis, Adelson’s allocation of funds can be similarly perplexing. 

Researchers at Tel Aviv University, working at the Dr. Miriam and Sheldon G. Adelson Center for the Biology of Addictive Diseases, have conducted groundbreaking research into the science of cannabinoids. Scientists at the center, underwritten by one of Adelson’s many philanthropic gifts to Jewish charities and institutions, recently published a study showing that patients with multiple sclerosis may benefit significantly from THC and CBD, the major cannabinoids in medical marijuana. 

On the other hand, a $2.5 million Adelson donation was instrumental in defeating Florida’s 2014 bid to legalize the use of that same medicine. And he may reprise that role in 2016. 

It Helps to Have Friends in Florida 

For Florida prohibitionists, the path to Adelson’s cash goes through the casino magnate’s longtime friends, Mel and Betty Sembler. Sembler, a Florida developer and ex-(non-Italian-speaking-)ambassador to Italy, has long served as one of the Bush family’s major fundraisers. His talents have served generations: George H.W. to George W. to Jeb. Though Sembler made his fortune developing shopping malls across the American South, he made his name in the drug rehabilitation game. 

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In 1976, Sembler and his wife Betty founded Straight Inc., a youth drug treatment program that would go on to enroll more than 12,000 participants. Straight eventually came under state scrutiny for false imprisonment and mistreatment of patients. Eventually the Semblers shut down Straight and re-christened it the Drug Free America Foundation, which mingles funds, staff, and an office with a group the federal government contracts to help small businesses develop their own drug-testing programs for employees. In other words: In Florida, Adelson’s support props up the Semblers, who profit directly from the war on drugs. His millions in campaign contributions are critical to keeping Sembler’s commodification of the drug war viable. 

In anticipation of Florida’s upcoming Prop 2 battle, a reprise of the 2014 MMJ fight, the developer told the Tampa Bay Times that his motivation was to “save lives and people’s brains” since cannabis is “not a medicine.” Sembler claimed his struggle against legalization was made more difficult by the financial power of legal cannabis, which he contrasted with his own commercial efforts, where “there’s no profit.” 

Sembler’s influence doesn’t end at the Florida state line. According to Sembler, the governors of Arizona and Massachusetts have asked him for help — and perhaps a letter of introduction to Adelson’s checkbook — in defeating legalization efforts on the November ballot in those states. 

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What’s Adelson’s Motivation?

The most intriguing theory on the thread that binds all these contradictory patterns was spun by Sunshine State News executive editor Nancy Smith. Reviewing Sembler’s unapologetic history with Straight Inc.’s coercive methods and cover-ups, Smith writes that 

“[I]t was Sembler who went to work hustling money out of Adelson to oppose Amendment 2, and Adelson capitulated. Think about it. Adelson has spent hundreds of millions of dollars on marijuana research to get a single breakthrough on multiple sclerosis. His institute has been cautious. He’s going the Food and Drug Administration route. Now, all of a sudden, he’s shown a loosely written ballot amendment, penned and backed by a rich and powerful Democratic lawyer (John Morgan)… You can imagine, with Sembler’s special twist how that would offend Sheldon Adelson. …. My theory is this–and that’s all it is, a theory–Sheldon Adelson is convinced John Morgan’s amendment is a free-for-all invitation not to cure disease or lessen suffering, but to legalize what he believes (with a little help from his friend Mel Sembler) is an out-of-control and destructive way of life.

There are other theories as well. Two years ago Lee Fang, now an investigate reporter at The Intercept, wrote a piece for Vice speculating that Adelson’s MMJ opposition in Florida stemmed from his desire to establish casinos in the Sunshine State. The chain of influence, as Fang rolled it out, went something like this: Opening table gaming to non-tribal companies in Florida required support from the governor and legislators; in 2014, Gov. Rick Scott was running for re-election and opposed the medical marijuana initiative; so to boost Scott and gain his favor, Adelson pumped money into the anti-MMJ campaign. 

As theories go, Fang’s hung out far on the ledge. (Why wouldn’t Adelson just donate to Rick Scott’s re-election campaign?) But it offered readers a glimpse into the challenges faced by those who would explain Sheldon Adelson’s motivations and strategies. To put it simply: They are not simple. The effort to counteract his cash infusions won’t be, either. 

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