Donors to Dr. Jackson’s campaign now include Ronald S. Lauder, the cosmetics billionaire and one of Mr. Trump’s oldest acquaintances, who gave Dr. Jackson $2,800 for the runoff race and another $2,800 for his general election campaign, according to campaign finance reports. Others who donated to Dr. Jackson’s campaign included former West Wing colleagues of his like Sarah Huckabee Sanders, the former White House press secretary; Hope Hicks, a senior adviser to the president; Raj Shah, a former top White House spokesman; and Mr. Clark.
The Trump operatives also helped Dr. Jackson hire Jeremy Sheftel, a Florida-based operative with field experience, to run the campaign. And they worked with the White House to ensure that Mr. Trump endorsed Dr. Jackson, even inviting him aboard Air Force One when the president visited Dallas last June. And Dr. Jackson benefited from the runoff election’s being delayed by a month because of the coronavirus, giving him more time to catch up.
His opponent, Mr. Winegarner, however, tried to diminish Dr. Jackson’s interest in the district, to which he had only recently returned. He aired an ad that told voters, “We are Ronny’s backup plan,” a reference to his dashed hopes of becoming the secretary of veterans affairs.
Dr. Jackson’s advisers, in turn, framed his campaign as another example of a Trump-backed candidate seeking to drain the swamp, depicting Mr. Winegarner, who used to work for Mr. Thornberry, as part of a broken system in which a lobbyist and former Capitol Hill staff member becomes the immediate favorite to take his old boss’s job.
Playing into the role of marauding outsider, and aided by the political advice of Mr. Clark and Mr. Stepien, Dr. Jackson also leaned into national political controversies. Despite serving as President Barack Obama’s physician before Mr. Trump took office, he backed a conspiracy theory promoted by Mr. Trump that his predecessor had spied on his campaign — an accusation Mr. Trump has made while offering no evidence to back it up.
“President Obama weaponized the highest levels of our government to spy on President Trump. Every Deep State traitor deserves to be brought to justice for their heinous actions,” Dr. Jackson tweeted in May, drawing a rebuke from former Obama administration officials who called his statement “truly shameful” and an example of his “lying for Trump” in order to win a congressional primary.