David Bossie
David Bossie, the chair of the Maryland delegation to the Republican National Convention, announces Monday that the delegates are unanimously supporting Donald Trump for president. Credit: Screenshot, Maryland Matters / Maryland Matters

MILWAUKEE — There is only one celebrity in the Maryland delegation to the Republican National Convention, and it isn’t an elected official, party donor or business titan.

He’s not a household name, but David Bossie is a central figure in former President Donald Trump’s orbit — and in the broader conservative political movement.

By day, he’s the head of Citizens United, the provocative national conservative organization that has literally changed the way campaigns are waged in America.

“It’s a great organization,” said Joe Arpaio, the controversial former Arizona sheriff who has become an icon in the MAGA movement.

Closer to home, Bossie is Maryland’s representative to the Republican National Committee and chair of the state’s delegation to the GOP convention this week. It was the Ashton resident’s task Monday afternoon to inform the nation that Maryland’s delegation was unanimous in its support for Trump.

Friends and admirers tout Bossie’s political acumen and ability to play multiple roles in conservative politics. They also describe him as a devoted family man who loves his country and his state.

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The head of a national political reform organization that formed to oppose Bossie’s work says he “represents everything that’s broken in our politics.”

On Wednesday, Citizens United will debut a feature-length Bossie-produced documentary called “Trump’s Rescue Mission: Saving America.” In a convention already marked by Trump hagiography, this may mark a new high — or low, depending on one’s viewpoint — of the Trump worship on display.

“This is an important film in the most important year in the history of America,” Bossie told Charlie Kirk, head of pro-Trump youth organization called Turning Point USA on a podcast Saturday.

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Bossie told Kirk that Trump was planning to introduce the movie Wednesday, but that was before Trump survived an assassination attempt in Pennsylvania on Saturday. Bossie did not respond to messages left over several days with Citizens United and the Maryland Republican Party, and it’s not known if Trump still plans to speak at the screening.

Coincidentally, the movie will be shown in the Miller High Life Theater, the same one where Theodore Roosevelt spoke in 1912, just minutes after surviving an assassination attempt across the street.

It’s not Bossie’s first foray into filmmaking. In 2016, Citizens United debuted “Torchbearer,” about “Duck Dynasty” patriarch Phil Robertson, at the GOP convention in Cleveland. Robertson had become a hero to conservatives over his multiple battles with government regulators.

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More famously, Citizens United produced an anti-Hillary Clinton movie that became the basis of a 2010 U.S. Supreme Court case that dramatically reordered the nation’s campaign finance system. Citizens United challenged campaign finance limits at the time, arguing that they impeded its ability to promote “Hillary: The Movie.”

The high court’s ruling essentially equated campaign donations with speech, paving the way for unlimited spending in most elections, and turbocharging the rise of “dark money” in politics. The fallout is everywhere: On airwaves thick with political advertising and in the prevalence of shadowy groups with neutral names and hard-to-trace funding streams, pushing agendas.

Notably, former President Barack Obama lectured the Supreme Court for the Citizens United decision during his 2011 State of the Union address.

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“David Bossie represents everything that’s broken in our politics,” said Tiffany Muller, president of End Citizens United, which supports candidates who favor countering impacts of the Citizens United ruling. “The Supreme Court case that bears his organization’s name opened the floodgates of unlimited and undisclosed money in our elections and fundamentally changed the way elections are run in America.”

Citing a 2019 controversy in which Bossie and Citizens United were accused of trying to cash in on their association with Trump by using his image in fundraising appeals, Muller said Bossie has “sought to line his own pockets while feeding into the most extreme elements of the MAGA movement. Bossie’s influence — both in Maryland and nationally — runs deep and continues to contribute to the erosion of our democracy.”

Bossie has long been unapologetic about the long-term political and societal impacts of the Citizens United ruling, calling it “a victory for free speech.”

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“At its core, the Citizens United decision encourages more participation in America’s political process,” he wrote in a Fox News commentary on the decision’s 10th anniversary. “Much to the dismay of the left, Citizens United v. Federal Election Commission was a case about free speech and whether the First Amendment protected the American people from government attempts to limit speech. Nothing more, nothing less.”

Bossie has also gleefully accused End Citizens United of being a partisan organization. The group, through it’s political action committee, has endorsed Democrats who support campaign finance reform almost exclusively since its founding in the wake of the ruling — including Prince George’s County Executive Angela Alsobrooks in this year’s Maryland election for U.S. Senate.

‘Donald Trump must save America’

Bossie, 58, was a confrontational conservative well before the political rise of Donald Trump’s MAGA movement.

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He cut his teeth in politics on former President Ronald Reagan’s campaigns and as a national leader of the Young Republicans. Later, he was a top aide to former Rep. Dan Burton (R-Indiana), who ran high-profile investigations of Bill and Hillary Clinton when they occupied the White House.

Bossie took over Citizens United in 2000. The group was founded by Floyd Brown, who produced the infamous “Willie Horton” ad that helped sink Democrat Michael Dukakis’ presidential campaign in 1988.

Bossie’s influence in Maryland spiked considerably in early 2016 when he ousted the state’s long-time Republican national committeeman, Louis Pope, who came from the party’s Main Street/country club wing. It was a harbinger of the growing Trump movement in the state GOP and throughout the country.

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The national committee members are the state party’s conduit to the national Republican organization.

“Dave’s a great partner,” said Nicolee Ambrose, Maryland’s Republican National Committeewoman — whose own victory in a bitter internecine election in 2012 created a new conservative power dynamic in the state GOP.

During the 2016 election, Bossie took time off from Citizens United to become Trump’s deputy campaign manager. Since then, he has remained an outside adviser and frequent cheerleader of the ex-president’s, helping to run Trump’s war room during his first impeachment case.

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“Donald Trump must save America, and that’s why we made this movie,” Bossie told Kirk Saturday. “We either win this election in America and Donald Trump takes over the White House, we win the House and Senate and save America, or we are destined for the ash heap of history.”

The movie trailer displays Trump in his macho best, striding across stages, filmed at flattering camera angles, his rhetoric resolute. And this was before he survived Saturday’s shooting, which has boosted his stature among supporters to epic, almost mythical proportions.

In the trailer, President Joe Biden is portrayed as bumbling and stumbling. And the film emphasizes Trump talking points about crime and immigration, inflation and the economy.

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“Everybody must see the film so you can educate yourself and tell your neighbors and family why Joe Biden, and not just Joe Biden, but the crazy left and their disastrous policies, what they have done to America over the past four years, versus Donald Trump’s four years of peace and prosperity,” Bossie said on Kirk’s podcast. “When Americans are looking at this film, there’s no way to come out of it not being for Donald Trump.”

Among Maryland Republicans, Bossie is known for his pipeline to Trump intimates and even to the ex-president himself. He helps elevate a Democratic state that doesn’t always figure prominently in national GOP politics, they say.

“In a typically blue state, it’s nice to have someone in that inside-baseball role,” said Wicomico County Executive Julie Giordano (R), a convention delegate.

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Maryland Republicans say Bossie can also smooth over relations with Trump and his associates when GOP politicians in the state try to distance themselves from the former president out of political necessity. They even attribute the delegation’s prime Milwaukee hotel space – just around the corner from Trump’s hotel – to Bossie’s intervention, when bigger and more consequential delegations find themselves out in suburbia.

“He (Bossie) loves our state,” said Del. Kathy Szeliga (R-Baltimore County), a conservative leader in Maryland and convention delegate. “He could live anywhere and he lives in Maryland. It’s nice to know that he gets us — and he’s right there with President Trump sharing about the struggles and concerns of the people in Maryland.”

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