Since 2015, Donald Trump and his allies have bent and broken the law to boost his political fortunes. These breaches occur with an audacious frequency. But the most recent scheme by President Trump’s supporters proves that they can always get more audacious.

In December, news broke that a nonprofit group founded by a Trump ally raffled envelopes of cash to attendees at an event targeting black voters in Cleveland. The event, hosted by the Rev. Darrell Scott’s Urban Revitalization Coalition, honored White House official Ja’Ron Smith and featured “lavish” praise of Trump and his policies. The “$25,000 Cash Giveaway” was part of the group’s nationwide strategy to lure black voters into listening sessions about Trump. While many have rightly condemned this effort as cynical and disrespectful, it could also put the coalition and White House staff in legal trouble.

The coalition was founded in 2017 as a section 501(c)(3) nonprofit entity and certified by the Internal Revenue Service in April 2019. Under the law, section 501(c)(3) organizations are “absolutely prohibited” from directly or indirectly participating or intervening in any political campaign on behalf of any candidate for elective public office.

The coalition claims that its events are nonpartisan, but it has taken numerous steps that belie the group’s support of Trump’s reelection bid. For example, the coalition website highlights its founders’ roles on the National Diversity Coalition for Trump, an organization that “strongly supports Donald J. Trump for President of the USA.” Last year, the coalition published a report stating that financial support helps the “URC continue to fulfill its mission and purpose as PROMISED by President Donald J. Trump to ‘Make America Great Again.’ ” The same report also bragged that the coalition is working to “increase the 8% African-American vote from 2016 by 25% in the 2020 Presidential Election.”

Increasing African American voter participation is a laudable and legal goal. But the “8%” figure referenced by the coalition does not reflect overall black participation in 2016, as the group’s language implies; it’s the estimated percentage of black voters who supported Trump. Voter registration drives can be prohibited political activity for 501(c)(3)s if they are “conducted in a biased manner that favors” a partisan candidate. In addition, public records show that in 2018, the coalition received a $238,000 donation from America First Policies, a politically active group backing Trump’s reelection. These facts suggest that the coalition is exploiting tax laws to serve as a front for political advocacy.

Those partisan ties may jeopardize the coalition’s nonprofit status, but Smith’s reported attendance at the “giveaway” could also have legal implications. Federal workers are allowed to engage in political activity on their personal time, and some, like Smith, can engage in politics while on duty. Government funds, however, cannot be used for these officials’ attendance at political events.

Smith’s official Twitter account suggests that he spent the weekend of the raffle in Cleveland attending several events for his government job. Trump campaign officials have disavowed knowledge of the coalition’s event, and the White House declined to comment for a Politico report about it. But in a video on its YouTube page, the coalition claims that its work was “commissioned by President Donald J. Trump.” If the White House covered Smith’s travel to Cleveland, the government may need to be reimbursed for costs associated with any portion of his travel related to political activity.

The coalition claims that its cash giveaways for sitting through pro-Trump talking points are legal and will continue. But recent history offers ample reason for caution. Last year, Democratic presidential candidate Andrew Yang was lambasted for offering raffle money to visitors on his campaign website. Ironically, in 2012, President Barack Obama was accused of gifting cellphones to voters in what was exposed as a “Pants on Fire,” race-baiting mischaracterization of the federal government’s Lifeline program, which aimed to expand telephone communications access to low-income Americans.

Here, the coalition’s status as a section 501(c)(3) nonprofit group presents credible and serious legal questions regarding its partisan ties and “charitable” activity. The racial targeting of the coalition raffles invites even more suspicion. If White House staffers show up at cash giveaways that promote Trump as he pursues reelection, they could find themselves in the crosshairs of ethics officials inside and outside the government.

Trump and his allies have repeatedly faced legal jeopardy because of inappropriate efforts to influence electoral politics. These incidents include campaign finance and Hatch Act violations and, of course, the president’s interactions with Ukraine. Such ethical abuses have become a signature of the Trump years. The coalition’s cash-giveaway scheme suggests that some of the president’s surrogates are still reaching new depths.

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