Donald Trump is less than six months into his presidency, yet one of the organizing principles of his political operation is already becoming clear: payback.

In private, Trump has spoken of spending $10 million of his own money to defeat an incumbent senator of his own party, Jeff Flake of Arizona, according to two sources familiar with the conversation last fall. More recently, the president celebrated the attacks orchestrated by a White House-sanctioned outside group against another Republican senator, Dean Heller of Nevada, who has also been openly critical of him.


Fear of Trump reprisals has led one Republican congresswoman, Martha Roby of Alabama, to launch an intense campaign to win over a president who remembers every political slight — and especially those who abandoned him following the October release of the 2005 “Access Hollywood” tape in which he bragged about sexually assaulting women.

At the time, Roby called Trump “unacceptable” and said she wouldn’t vote for him. But the president, who is popular in Alabama, ended up carrying her district by a wide margin. Since the inauguration, she has gone to the White House four times to attend Trump-hosted events and on two other occasions to meet with his daughter Ivanka — at the White House's invitation. During the Rose Garden celebration following the House’s passage of the health care bill, the four-term congresswoman offered the president a personal compliment while shaking his hand: “Good job,” she told him, according to a source close to Roby who was briefed on the exchange.

White House officials have taken notice of Roby’s efforts to make amends and view her efforts with some skepticism. While in the Oval Office for a NASA bill signing in March, Roby sidled up next to Trump — putting her front-and-center for the photo-op. Behind her push for the president’s approval is a stark political reality: She is facing a fierce primary challenge from a Trump stalwart who has turned her past opposition to the president into the focal point of his campaign.

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The backstage machinations provide a glimpse into Trump’s approach to politics and how it is shaping the 2018 midterm election landscape. Trump’s obsession with loyalty and penchant for keeping close track of personal slights — both well-documented by his biographers and in coverage of his presidency — color his approach not only toward his political foes but toward his own party’s candidates, even at the risk of jeopardizing GOP incumbents.

“The president once told me that the most important lesson he learned from Roy Cohn was loyalty,” said Chris Ruddy, a longtime Trump friend and the chief executive of the conservative website Newsmax, referring to the ruthless New York fixer and attorney who mentored the president early in his real estate career. “He believes in that strongly in all his friendships.”

Even before the 2016 campaign was over, Trump began talking about how, as president, he would strike back at members of his party who wronged him, according to a senior campaign aide. Administration officials have been struck by his ability to recall what Republicans said about him before his victory, especially those who criticized him following the release of the “Access Hollywood” tape — a decisive moment that crystallized for the then-GOP nominee who his true friends were. Even today, chief of staff Reince Priebus, according to one administration official, is routinely reminded that he told Trump to quit the race.

Two White House aides say the president now relishes that some of those who crossed him, like Roby, are scrambling to get in his good graces.

They have good cause for worry. Just days before taking the oath of office, Trump mounted a successful effort to oust a fierce intraparty critic, Ohio GOP Chairman Matt Borges. The president has also fumed about Flake, who called on Trump to drop out after the “Access Hollywood” footage surfaced. Backstage, before an Arizona election rally last fall, Trump spoke animatedly about his desire to find a primary challenger to the senator — at one point saying he would put up $10 million toward the anti-Flake effort.

Flake has already drawn a pro-Trump opponent, former state Sen. Kelli Ward. And two other allies of the president, Trump campaign Chief Operating Officer Jeff DeWit and former state GOP Chairman Robert Graham, are considering bids. DeWit remains close with the administration and was at the White House last month to attend meetings.

Heller, who announced months before the election that he didn’t intend to support Trump, is also out of favor with the president. The Nevada Republican recently came under attack from a pro-Trump outside group over his refusal to support the Obamacare repeal bill — a move that rankled Senate Majority Leader Mitch McConnell, who viewed it as an unnecessary effort to undercut one of his most politically vulnerable members.

Yet Trump has told friends that he loved the anti-Heller blitz, convinced that the senator was trying to use his opposition to the bill for his political gain and that a show of force was needed, said two people familiar with the discussions. When it comes to Flake and Heller, the disdain is personal — three sources familiar with the president’s thinking said Trump believes the senators are determined to undermine him.

Aspiring candidates face possible blacklisting, too. Troy Downing, a Montana Republican running for Senate, has been flagged by people close to the president for his past anti-Trump tweets — including one from March 2016 in which Downing derided Trump as “either a liar or an idiot.” (One person close to Downing, however, said the candidate visited the White House in May to meet with political aides and was warmly received.)

In Missouri, GOP Rep. Ann Wagner had long been considered a top-tier Senate contender. Yet last week, in a surprise announcement, she said that she would instead run for reelection. One factor shaping her thinking, said two sources close to her, was the conclusion that her past criticism of Trump — which had been noted by White House aides — could hurt her standing in a state that he won by nearly 20 percentage points.

Some Trump friends expect the weight of the presidency will dull his appetite for revenge against those who have crossed him. They point to his increasingly cordial relationship with Texas Sen. Ted Cruz, a primary rival who Trump long criticized for failing to support him more aggressively once the nomination fight was over. Initial predictions among Trump aides that the president would go after the senator, who is up for reelection in 2018, have faded as the two have worked together on a host of legislative issues. The two, along with their families, met for dinner in March.

“While the president has never been a ‘turn-the-other-cheek’ kind of guy, I believe that he is aware that he has a better chance of pressuring establishment Republicans into his congressional majority to get anything done than he does [with] liberal Democrats,” said Roger Stone, a longtime Trump friend and informal political adviser. “A purge of the party establishment, while it would be delicious, is not on the agenda — unless, of course, the president became convinced they willfully inspired to delay or defeat his programs.”

That may be the case with Roby, who has decided her best play is to win over the president she once lambasted. The effort began the night of his election, when she hammered out a 3 a.m. tweet, congratulating him. “I’m eager to get to work,” she wrote.

The move, her detractors insist, is a cynical one. Roby’s primary opponent, state Rep. Barry Moore, notes that he was the first elected official in Alabama to endorse Trump and that he attended the August 2015 rally in Mobile that catapulted Trump’s national bid. The president has become the centerpiece of Moore’s campaign: On the personal biography page of his campaign website, Moore mentions Trump’s name no fewer than eight times.

“He knows I was there when the times were tough, and long before he had the nomination,” Moore said. “I was there for him when he needed us.”

“A lot of the Republicans panicked, I think, and were more concerned about saving their political careers than supporting our nominee,” added Moore, who is fashioning himself as a Trump-style insurgent. “He had a bunch of cut-and-run congressmen.”

Roby’s aides insist her relationship with the administration has been nothing but warm. And there have been other hints at cooperation. In February, Trump gave Roby a retweet when she congratulated Attorney General Jeff Sessions on his confirmation. In April, the president nominated the congresswoman’s chief of staff to a Justice Department post — trophies that Roby’s advisers eagerly highlight.

While Roby’s aides don’t deny past tension with Trump, they say they’ve gotten no indication the president wants to unseat her.

“The White House has made it clear from Day One that it is committed to working with Congress to deliver results, and Rep. Roby has a proven track record of consistently supporting President Trump’s agenda,” said Emily Taylor, a Roby spokeswoman. “From being invited to NASA and VA bill-signing ceremonies, to sitting in the Oval Office to help the president build support for the Republican health care bill, Rep. Roby has enjoyed a positive working relationship with the Trump administration.”

For now, Trump aides don’t expect him to weigh in on Roby’s race with an endorsement for her opponent. At the same time, they don’t expect him to take steps to publicly back the incumbent.

Roby is just hoping to avoid Trump’s wrath, and that means doing whatever she can to ally herself with him.

In late March, as the debate over the health care bill raged, Roby and other House members were asked to come to the White House. At one point, the congresswoman was asked whether she supported the legislation. As she later recounted in a video posted to her Facebook page, she looked the president in the eye and told him she did.

The president told her he appreciated it.

Annie Karni contributed to this report.

