President Donald Trump personally views his rallies as determinative, and he is bullish about Republicans’ Senate chances. | Andrew Harnik/AP Photo White House Inside Trump's crash course on midterm politicking Undergirding Trump's rally schedule is insight from political director Bill Stepien, who evaluates the latest campaign data each morning on more than 70 races.

President Donald Trump set off early alarms when he signaled an interest in Kelli Ward, a right-wing candidate in Arizona’s competitive Republican primary for a U.S. Senate seat.

But after reviewing the polls and conferring with political advisers and Senate officials, who warned him that Ward was likely to lose, Trump decided to subordinate his gut instinct for the bold stroke and ultimately stayed neutral in the race.


So when Ward lost to her establishment GOP rival, Martha McSally, it was easier for Trump to back the Arizona congresswoman, despite her past criticism of him. Now, with a McSally win seen as crucial to preserving the GOP’s Senate majority, national Republicans are thankful they don’t have a family feud on their hands in the state.

It was one of several cases in which Bill Stepien, the White House’s political director, was able to help guide the president — with polling numbers and a deep knowledge of national campaigns — in ways that don’t always match Trump’s shoot-from-the hip style.

In interviews with nearly two dozen White House officials, presidential advisers and Republican operatives working on the midterms, Stepien’s political office is credited with doing the early spadework to put their famously impulsive boss in the best position to help Republicans.

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The partnership between Stepien and Trump marks a kind of crash course for the president, who as a New York real estate mogul had little experience with congressional campaign politics before he launched his 2016 campaign for president. Aides say Trump, recognizing that the trajectory of his presidency is at stake, has been willing to listen, absorbing poll data and forgiving past grudges as he works to limit Democratic midterm gains.

Each morning, Stepien sifts through more than 70 races, analyzing the latest polling and intelligence gathered through conversations on the ground and in Washington, and moving the contests up and down, backward and forward, left and right. Depending on the day, Stepien’s team sees a narrow path to keeping the House, according to senior officials and advisers familiar with election planning. But a recent internal memo from Stepien also tempered expectations, conceding that such a prospect is “challenging,” and other White House officials are now saying publicly that retirements are making it tough to retain House control.

Regardless of the outcome, much of the attention on Nov. 7 will turn to Stepien, who works behind the scenes. Besides Trump himself, the political director is poised to get notable credit if Republicans have a better-than-expected showing, but he is also on the hook if the GOP takes a drubbing. In midterm elections, the president’s party has lost, on average, 25 House seats since 1946. And the polling in 2018 indicates that the GOP may lose that many seats — and its House majority with it.

Stepien, 40, clean-cut and a veteran of former New Jersey Gov. Chris Christie’s campaigns, has been a close adviser to Trump since the 2016 campaign on everything from endorsements and messaging to his travel schedule. In recent months, he teamed with the 2020 reelection campaign and GOP committees to create a game plan to raise tens of millions of dollars and dispatch Trump to more campaign trail stops than his two immediate predecessors.

“While other parts of the White House were in disarray, the president’s political shop was prepared to utilize his time and the bully pulpit to motivate voters and sell a positive legislative agenda,” said Bryan Lanza, a spokesman for Trump’s 2016 campaign.

If Republicans lose badly, though, much of the second-guessing will circle back to Stepien’s team. Other political figures working with the president are viewed as having more protections: Trump recently asked Republican National Committee Chairwoman Ronna Romney McDaniel to serve a second term, and Trump relies heavily on 2020 campaign manager Brad Parscale’s data operation.

“These guys are sitting there. The whole world is watching them. There are so many critics,” said Matt Schlapp, George W. Bush’s political director in 2004. “And everything is on the line.”

Stepien’s job is not to manage campaigns, but to advise Trump about the political landscape so he can advance his policies and agenda.

This summer, his office worked with other Trump advisers to arrange the president’s flurry of rallies and fundraisers ahead of the midterms. Stepien, often in early-morning phone calls, provided the president with the pros and cons and the numbers behind a candidate or race. In August, aides presented Trump with their plan for his final two-plus months of rallies and fundraisers before the midterms. The president told them it wouldn’t be enough — and to add more stops. His final blitz reflects that.

“He’s the boss. He makes the final decision,” Stepien said in an interview. “But when he often asks for input, I weigh in and make a recommendation. And I could only do so because we’ve spent the time kicking the tires.”

Stepien’s team last week dropped Trump into Montana, Arizona and Nevada to take advantage of early voting — each of the states has at least two-thirds of their votes cast before Election Day. Florida, where Trump will be next week, is another major early-voting state.

Trump personally views his rallies as determinative, and he is bullish about Republicans’ Senate chances, particularly in Montana, North Dakota and Indiana — all states where he has held rallies in recent months.

The political shop also dispatched Trump to Delaware County, Ohio, in August to campaign for Republican Troy Balderson, then a state senator, in the special House election against Democrat Danny O'Connor. Balderson ultimately squeaked out a narrow win, which Republicans credited in part to Trump’s appearance.

Each morning White House political director Bill Stepien sifts through more than 70 races, analyzing the latest polling and intelligence gathered through conversations on the ground and in Washington. | John Shinkle/POLITICO

But Trump’s presence can be tricky for Republicans running in districts where the president isn’t popular. And since district-by-district public polling is often unavailable and/or suspect, much of the onus is on Stepien to read the tea leaves. For instance, the president recently went to Kentucky to support Rep. Andy Barr’s reelection bid, a decision that not every Republican thought would help Barr.

“If Barr winds up winning by a point or two, which I think is possible, it would be hard not to look at the president’s rally in Richmond, Ky., and say, ‘It didn’t help,’” said Scott Jennings, who worked in Bush’s political shop during the 2006 cycle.

Trump has also shown a willingness to back candidates who had previously criticized him or broken with his agenda, in part because his political advisers have helped convince the president of the importance of doing so.

Trump threw himself into Nevada with Republican Sen. Dean Heller, a candidate who was critical of the president early on. Trump urged Republican Danny Tarkanian to drop his bid against Heller and instead run for the House — a move that set the tone for the president’s hatchet-burying approach to the midterms.

In a New York primary, Trump backed incumbent Republican Rep. Dan Donovan over former Rep. Michael Grimm, despite the fact that Donovan had voted against Trump’s signature tax bill and that Grimm was using much of his comeback run to argue that his opponent was insufficiently loyal to Trump. Donovan ultimately came from behind in the polls and won.

But Trump stayed out of other primaries, such as in Arizona. Trump’s public flirtation with Ward in August 2017 came before Sen. Jeff Flake announced he wasn’t seeking reelection. By withholding his endorsement, Trump avoided siding with weaker general-election candidates Ward or former Maricopa County Sheriff Joe Arpaio, but also steered clear of alienating their conservative supporters.

Unsurprisingly, though, Trump sometimes does his own thing.

After Republicans urged him to stay out of the Minnesota House race against incumbent Democrat Collin Peterson, given Peterson’s work across the aisle, Trump weighed in for underdog Republican Dave Hughes. The surprise tweet sparked a wave of “WTFs” from the political shop. Trump also was not expected to back GOP megadonor Foster Friess in the Wyoming governor’s race, but did so on the recommendation of his son Don Jr.

But most of the time, the president, his party and Stepien’s office have been on the same page — particularly in the Senate.

In Mississippi’s nonpartisan Senate primary, Trump backed Cindy Hyde-Smith — a Democrat until 2010 and the preferred GOP establishment candidate — over Chris McDaniel, the hard-line conservative. The endorsement came after Hyde-Smith’s campaign met a series of benchmarks related to fundraising and polling. McDaniel lashed out at the president and accused him of being beholden to the party establishment.

“He is his [own] adviser,” a Republican close to Trump said. “But the infrastructure and architecture [inside the White House,] he’s using well.”

Stepien and the president have a bond rooted in the rambunctious 2016 campaign.

When the president regales crowds in private fundraisers with tales of his upset 2016 victory, he still credits Stepien as the lone staffer who said he could win when the early returns trickled in and the GOP candidate was behind in key states. Trump of late has been asking him to give the audiences of donors a state of play on the midterms.

After shocking the world with his victory, Trump has become by nature a political optimist. But few around the president felt he was being served well politically by senior White House advisers in his first year. Power struggles over even minute matters normally handled by the political office were common.

Stepien, despite his title, was largely relegated to a background role, overshadowed by chief of staff Reince Priebus, the former RNC chairman, and chief strategist Steve Bannon.

The knock on Stepien was that he didn’t have Trump’s ear, despite being brought on to the president’s campaign in August 2016 by his son-in-law, Jared Kushner, after Christie broke with Stepien over his alleged knowledge of the Bridgegate plot, in which key traffic lanes were closed down as political retribution (Stepien denies any knowledge of the scheme). He impressed Bannon, and Kushner pushed to land Stepien the White House job.

But in that first year, party leaders and politicians often dealt with higher-level aides, or Trump directly. And fair or not, Trump confidants started questioning Stepien’s operation. Criticisms intensified after the party’s failed effort to repeal Obamacare.

The disastrous handling of the Alabama Senate race didn’t help, either, even though the some in the White House and other outside advisers had warned Trump to stay neutral in the GOP primary between the establishment choice, then-Sen. Luther Strange, and conservative firebrand Roy Moore. When Moore won the primary, they recommended that Trump not embrace a man accused of sexual misconduct, but the president did so anyway, and was embarrassed by the loss.

Late last year, Republicans around Trump began sounding the alarm that they weren’t prepared for the upcoming election. Corey Lewandowski, Trump’s former campaign manager, wanted the president on the road more stumping at rallies as the titular head of the party. The president reshuffled his staff and tapped Johnny DeStefano, who initially ran the office of presidential personnel, to help Stepien run the political office.

Observers said DeStefano and Stepien complement each other. Stepien has a background in polling, data and grassroots organizing, while DeStefano has a broad portfolio and network, having come out of the upper ranks of Capitol Hill staffers. John Kelly, who by then had replaced Priebus as chief, made sure Stepien was on Trump’s calendar every week. To prepare for the midterms, which have historically been brutal for a president’s party, Trump retreated with leaders to Camp David to get in sync.

With a new internal process in place, the political shop got to work on the elections with the expectation its efforts would be put to greater use.

“There’s not a single person on the political side the president trusts more than Bill,” one senior White House official said. “It was just getting Bill in the position to add as much value as he is capable of adding.”

Stepien’s office interviewed and surveyed hundreds of GOP candidates and compiled files on their voting records and statements, including their public remarks about Trump, who invited a crush of condemnation after the release of the “Access Hollywood” tape on which he bragged about groping women. The files became invaluable when Trump started shaping primaries with endorsements. And Stepien has been getting a lot more face time with the boss while traveling with him to events.

“Bill Stepien is a very good political director,” Lewandowski said. “It’s going to be much easier to Monday morning quarterback this day after the election.”

Such goodwill has been possible because Trump’s endorsements have largely worked out thus far — and because the team is mostly on the same page regarding Trump’s hard-line political messaging.

But the first signs of finger-pointing are rising in Trump’s orbit. Some confidants scrutinized decisions to send Trump to areas where Republicans won’t appear with the president on the stump. They also questioned Trump’s stops in Texas and Mississippi — both seen as likely GOP wins in Senate races — so close to the midterms. Trump advisers defended the Mississippi stop as helping push Hyde-Smith over the 50 percent threshold she needs to avoid a late November runoff.

For Stepien, it all comes down to the final numbers.

As one Trump adviser put it, the difference between losing 25 seats and 50 seats in the House "is very likely the difference of who stays in the building.”