Cannabis Companies Court Trump: Strategic Moves Reflect Industry’s High-Stakes Gamble
Cannabis executives make political and corporate hires to curry favor with Trump administration amid hopes of federal reform.
In a clear indication of how high the stakes have become for the cannabis industry, several major players have made moves that observers interpret as efforts to gain favor with the Trump administration. These actions include a million-dollar political contribution to a Trump-aligned super PAC and strategic staffing decisions aimed at aligning more closely with the former—and potentially future—president’s circle.
A political action committee representing large cannabis multistate operators (MSOs) recently donated $1 million to MAGA Inc., a super PAC supporting Donald Trump. The donation, reported in recent filings, adds cannabis to the list of industries making calculated overtures toward a presidency widely seen as transactional.
Glass House Brands Reacts to ICE Raid by Hiring Former Homeland Security Official
Following a deadly July 10 immigration raid on its southern California farms, cannabis cultivation giant Glass House Brands made a striking personnel decision: hiring Guidepost Solutions, a labor compliance firm led by Julie Myers Wood, a former assistant secretary of Homeland Security under George W. Bush. The move followed the arrest of more than 370 workers, including children. One worker also died—believed to be the first fatality connected to a Trump-era immigration enforcement sweep.
Glass House’s public statement on August 5 revealed that nine of the arrested workers were employed directly by the company, while the rest were contracted via third-party farm labor agencies. In response, Glass House has cut ties with those labor providers and sought to reinforce its compliance protocols.
Teaming Up with Teamsters: A Strategic Labor Alliance
Glass House also inked a new labor peace agreement (LPA) with the International Brotherhood of Teamsters, a union increasingly viewed as Trump-friendly due to its leadership under Sean O’Brien, a vocal supporter of the president’s economic policies.
California cannabis companies with 10 or more employees are legally required to sign LPAs with bona fide labor organizations to maintain licensing. While the Teamsters are not dominant in cannabis agricultural labor compared to retail or indoor cultivation sectors, the move suggests an intentional alignment with Trump’s allies, industry watchers say.
“It is possible they went with the Teamsters since they’re more politically aligned with the Trump administration than other unions,” said Lucas Zucker, co-executive director of Central Coast Alliance for a Sustainable Economy (CAUSE), a California-based workers’ rights group.
A History of Transactional Politics: The Trump Context
Critics of the Trump administration argue that many political and business deals under his leadership resemble a “pay-to-play” model. From Paramount’s $16 million settlement ahead of a major merger to tech giants funding Trump’s inauguration in exchange for regulatory leniency, the pattern is familiar—and cannabis companies appear to be learning the rules of engagement.
The cannabis industry’s efforts are thus seen as a rational response to a government that rewards loyalty and monetary support.
“There’s a pretty obvious effort to try to curry favor with the administration,” said Hirsh Jain, a Los Angeles-based cannabis consultant and founder of Ananda Strategy. “And that’s understandable. It’s in their strategic interest.”
Multistate Operators Fund Trump Super PAC Through Industry PAC
Recent campaign finance filings show the American Rights and Reform PAC—formerly known as Legalize America—donated $1 million to Trump’s MAGA Inc. super PAC on March 26. The PAC’s funders include many of the largest MSOs in the country:
- Verano Holdings: $1.03 million
- Green Thumb Industries: $1 million
- Curaleaf Holdings: $750,000
- Cresco Labs: $750,000
- Trulieve Cannabis: $250,000
These same companies also funneled additional funds toward Trump-friendly political consultancies, including $300,000 to X Strategies, run by MAGA loyalist Alex Brusewitz, and over $1 million to Strategic Media Placement, a conservative-leaning ad firm.
Personal Connections to Trump Administration Already Exist
This is not the industry’s first flirtation with Trump-world. Notably, Trulieve CEO Kim Rivers and Cresco CEO Charlie Bachtell both attended Trump’s 2017 inauguration. According to political insiders, Rivers’ influence may have helped secure Trump’s endorsement of Amendment 3, Florida’s adult-use cannabis ballot initiative.
Their continued proximity to Trump’s inner circle raises the possibility of direct influence over federal cannabis reform efforts, particularly around rescheduling cannabis under the Controlled Substances Act—a move that could reshape the economics of the entire industry.
High Stakes: Federal Rescheduling Holds Key to Profitability
The cannabis sector’s sudden attention to Trump may seem surprising given the Republican Party’s historically inconsistent support for legalization, but the payoff could be enormous. The White House, under the Controlled Substances Act, holds the authority to reschedule cannabis, thereby lifting financial and legal burdens on the industry.
With the marijuana rescheduling process currently paused, a favorable ruling from Trump or a future DEA head like Terrence Cole could unlock banking access, tax relief under 280E, and new investment flows into cannabis companies.
Bribes or Business? Navigating Ethical Concerns
To critics, these actions may look like thinly veiled attempts to buy influence—but within the industry, they are more likely seen as smart business decisions. With federal legalization still stalled in Congress, and rescheduling delayed, many cannabis executives feel they can’t afford to remain politically neutral.
The perception that the Trump administration responds to financial loyalty means that cannabis companies are likely to keep aligning with the former president’s allies—whether through hiring decisions, donations, or union alliances.
The Industry Is Betting Big on Trump
From mega-donations to MAGA-aligned PACs to hiring former ICE officials and Trump-affiliated labor unions, cannabis companies appear to be embracing a pragmatic strategy: appease the power that controls your future.
Whether this high-stakes political bet pays off depends on whether Trump regains the presidency and chooses to act on cannabis reform promises. For now, the industry is playing the long game one campaign check at a time.
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