Trump Jr. Hits the Trail for GOP, Raising Dollars and Attention

Trump Jr.’s thinly staffed freelance political operation has raised over $1 million for Republican candidates at over 40 events.

Trump Jr. Hits the Trail for GOP, Raising Dollars and Attention
Donald Trump Jr., son of U.S. President Donald Trump and executive vice president of development and acquisitions with the Trump Organization Inc. (Photographer: Joshua Roberts/Bloomberg)

(Bloomberg) -- In Republicans’ fight to maintain control of Congress, there are the wealthy free-spending super PACs, the president’s stadium-filled rallies, and the traditional party machinery. Then there’s Donald Trump Jr.

The president’s oldest son is taking time away from Trump Tower to hit the campaign trail, holding his own rallies and headlining private fundraisers for candidates in both GOP strongholds and swing districts. He plans to spend the majority of his time before the election on the hustings seeking to energize the party faithful, according to a person familiar with the matter.

Trump Jr. Hits the Trail for GOP, Raising Dollars and Attention

“They like his style, and like his father he is unafraid and very much a fighter for values that they care about,” said Valentino DiGiorgio, chairman of the Republican Party of Pennsylvania.

This week, he held events in North Carolina and Georgia. He’s helped raise hundreds of thousands of dollars for Ohio gubernatorial candidate Mike Dewine, Nevada congressional candidate Danny Tarkanian and Mark Harris’s North Carolina congressional race.

Last week, Trump Jr. participated in five events for Senator Ted Cruz of Texas that raised some $460,000. Next week, he’s joining musician Kid Rock in a rally for Senate candidate John James in Oakland County, Michigan, an area that voted for Hillary Clinton in 2016.

Top Draw

One of three people entrusted with safeguarding the Trump family fortune, Trump Jr. has transformed himself from a typical Manhattan real estate executive into a top draw for GOP congressional candidates eager to have a Trump stump for them on the campaign trail.

Since June, Trump Jr.’s thinly staffed freelance political operation has helped raised more than $1 million for Republican candidates across more than 40 events around the country, said the person familiar with the matter.

He has also been raising money for various GOP political action committees, primarily the pro-Trump America First Action super PAC, even though Trump Jr. isn’t officially part of that organization.

For Republicans, the upcoming election represents a threat to the party’s dominance in Washington, where it controls the White House and both houses of Congress.

But with Democrats promising investigations into the Trump Organization’s affairs if they take control of the House, the stakes are high for the Trump family as well. Democrats have said they want to subpoena Trump Jr.’s phone logs, company records and banking statements as part of a wide-ranging probe into the family business.

Personal Risk

Trump Jr. also faces the prospect of Democrats targeting him directly as part of an inquiry into one of the biggest controversies stemming from his father’s presidential campaign: Trump Jr.’s participation in a June 2016 meeting at Trump Tower with a Russian lawyer that was arranged by a British publicist offering dirt on Hillary Clinton.

A number of Republican candidates are eager to bask in the attention the president’s son can bring. As a gun-toting New York businessman, Trump Jr. appeals to both blue-collar sportsmen and wealthy Republican donors.

At many events, he is joined by his girlfriend, former Fox News anchor Kimberly Guilfoyle, who’s also popular among Republicans and serves as vice chair of the America First Action super PAC. Guilfoyle, listed as cohost on nearly all of Trump Jr.’s events, has drawn enough of a powerhouse reaction from their audiences that she intends to branch off and do more events on her own, according to two people familiar with the matter.

Trump Jr.’s appeal can be traced in part to his social media accounts, where he regularly posts photos of himself wearing camouflage as he hunts big game and tries to catch sharks off the waters of Florida.

No Holds Barred

Trump Jr. also engages in no-holds-barred mudslinging, tweeting on Thursday, “If these leftists aren’t a mob I don’t know what is,” calling them “lunatics.” One of his Instagram posts last month compared sexual assault accusations against Supreme Court Justice Brett Kavanaugh to a childhood crush.

“He doesn’t feel the need to kowtow to political correctness. He says what’s on his mind,” DiGiorgio said.

His focus is motivating Trump’s base to make sure they turn out on Election Day, even if they aren’t particularly excited about the candidates on the ballot. His message is that casting a vote for Republicans is essential to protect his father’s accomplishments.

Trump Jr. is working independently of the White House and Republican National Committee, said the person familiar with the matter. He doesn’t have a speechwriter and often doesn’t prepare formal remarks for events. This spring, he hired Andy Surabian, a former political adviser to Steve Bannon, to help him with strategy and communications.

That off-the-cuff style has attracted controversy. On a recent swing through Texas, Trump Jr. made light of allegations that Kavanaugh, who told a Senate committee he liked beer, once was a heavy drinker.

“In this week in particular, you are not allowed to have a beer if you are a conservative,” he told a chuckling North Texas crowd in Wichita Falls dotted with cowboy hats and “Make America Great Again” baseball caps. “If you are a liberal, you can do cocaine and be the president. But that’s okay, we will hold ourselves to a higher standard.”

--With assistance from Jennifer Jacobs.

To contact the reporters on this story: Shannon Pettypiece in Washington at;Shahien Nasiripour in New York at

To contact the editors responsible for this story: Kevin Whitelaw at, Alex Wayne

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