Trump Complains about Campaign as Advisers Try to Focus on Attacking Harris

Caroline Yang for The Washington Post
Vice President Kamala Harris and her running mate, Minnesota Gov. Tim Walz, address the crowd at a campaign rally on Wednesday in Eau Claire, Wis.

Donald Trump’s candidacy appeared all but destined for victory only weeks ago.

He rose defiant from the bullet graze of an attempted assassination, hoisting his fist in the air with a unified party at his back, a growing lead in the polls, dissolving criminal prosecutions – and a struggling opponent, President Joe Biden, facing a full-blown revolt from within his own party. Trump mocked the idea of Vice President Kamala Harris becoming the new Democratic nominee, calling her “so pathetic.”

As staffers and allies gathered at the GOP nominating convention in Milwaukee last month, some privately discussed what administration jobs certain people wanted – and predicted a landslide election. There was talk of spending money in states where Republicans haven’t won in decades.

“At the convention, it was game over, and the Democrats realized that,” said Richard Porter, a member of the Republican National Committee from Illinois. “It felt like it was too good to be true, and it was. It’s amazing how quickly they coalesced behind another candidate.”

Trump now finds himself back in a dead-even contest and with new signs of strain in his orbit. In the face of new Democratic momentum, he has grown increasingly upset about Harris’s surging poll numbers and media coverage since replacing Biden on the ticket, complaining relentlessly and asking friends about how his campaign is performing, according to five people close to the campaign who like some others spoke on the condition of anonymity to discuss private conversations.

“It’s unfair that I beat him and now I have to beat her, too,” Trump told an ally in a phone call last weekend.

Allies have taken to finger-pointing over several events that seemingly went off the rails. Friends, Mar-a-Lago members and donors have logged their concerns with Trump, who then tells them to others, according to three people close to him. U.S. Senate allies and others are trying to get Trump focused on attacking Harris.

“We had a lot of good things happen in a row that were unsustainable, but we’ve hit a few speed bumps,” Sen. Lindsey Graham (R-S.C.), a Trump ally, said in an interview. “There’s been a rough spot.”

The Trump campaign, for its part, remains confident that he will win decisively in November, with aides saying they never took the advantages in July for granted or let their guard down. The former president remains ahead or tied in most of the swing states and continues to attract large crowds, with the cash on hand in total not far from the Democratic operation.

“The Trump campaign has never taken anything for granted and we always fight like we’re the underdogs,” Steven Cheung, a Trump spokesman, said in a statement. “That’s especially true after an assassination attempt on President Trump heading into Convention. Our sole job is to help President Trump win the election, and we’re going to beat the brakes off the dangerously liberal Kamala-Walz ticket.”

But for the first time since Trump established his dominance in the Republican nomination fight, his campaign has found itself publicly struggling to manage the daily news cycle as excitement around Harris has swelled along with her campaign activity. It has left people close to the campaign wondering why Trump and his team seemed ill-prepared, given that they had privately speculated for weeks after Biden’s disastrous June 24 debate performance that Harris was going to be the nominee.

“What’s happened in the last couple of weeks is we actually have a real race. This is a real presidential campaign. The Biden-Trump version of this was one event a week by each candidate, very rarely on the campaign trail and no real engagement,” said Kevin Madden, a Republican strategist who worked for Mitt Romney’s 2012 presidential effort. “Now this is going to be one of those campaigns where strategies matter, resources matter, time matters, and there is not much room for error.”

People familiar with the campaign’s inner workings say there is no staff freakout – nor have there been dramatic fights between senior advisers in recent days, a hallmark of previous Trump campaigns where things went awry. Staff have been meeting to discuss polls, spending and upcoming events at the campaign’s headquarters.

Cheung dismissed the allies and Trump advisers questioning the campaign’s effectiveness as “unnamed sources who have no idea what they are talking about and are doing nothing but helping Democrats.”

“We have always thrived under pressure because we take our cues from President Trump,” he said. “With his leadership, we continue to prove everyone wrong. Anyone on the outside who continues to complain simply hasn’t been battle-tested or gone through the adversity we have and come out on top.”

But there is no doubt that some of his big advantages have faded.

The fundraising edge advantages Trump enjoyed for two months has been swallowed by Harris’s $310 million fundraising surge in July – about $170 million more than he announced for the same month. The much-larger Harris campaign now appears poised to take advantage of a new outpouring of grassroots energy, including more than 1.3 million voters who signed up for campaign events since she entered the race for president, according to her campaign.

Despite going up with his first television spots of the general election, Trump and his allies are still being outspent in the battleground states. Over the first five days of August, Trump and his allies spent about $16.5 million on advertising, according to AdImpact, compared with about $23 million by Biden, Harris and their allies. From the beginning of March to early August, the Biden side has spent $309 million, compared with $110 million for the Trump side, according to the ad-tracking firm.

While Trump has repeatedly said Republican Party officials only needed to focus on election integrity, he has begun hearing from outside allies that he does not have a significant ground game in key battleground states. He has grown annoyed with some of the media focus on his campaign staff, suggesting to others that his advisers get too much credit. Some advisers have urged him to spend more on digital advertising, saying he is being pummeled online.

Democrats and some in Trump’s orbit have tried to highlight social media posts from Trump advisers and allies that they say show fear or bad messaging, while trying to stoke division in other ways. The Harris campaign has circulated posts and news releases about his staff, the pick of Sen. JD Vance (Ohio) as vice president, crowd size and other topics they say will grate on Trump and cause him to say controversial things.

“It’s easy to live in Donald Trump’s head,” one Harris aide wrote, suggesting a story about crowd size now that Harris draws a crowd as big or larger than Trump’s rallies.

Harris, meanwhile, has been traveling more on the campaign trail than Trump, who is fundraising this week in Florida. Since the June 27 debate, Trump has held eight campaign rallies, besides his nominating convention, including events in Minnesota, Florida and Virginia, all outside the main battleground map.

Harris will visit six states this week. Beyond interviews, the only event Trump has scheduled is a rally in Montana, a state where he is almost certain to win by double digits. Democrats wonder about the state of Trump’s operation, while the former president’s advisers note that he has campaigned for 21 months.

“Of all weeks when he has to blunt the momentum of Kamala Harris, you would have expected him to be very aggressive this week,” said Simon Rosenberg, a Democratic strategist.

Trump has begun asking friends and allies how his campaign staff is doing – a question that some say could lead to staff changes, though the former president has not said he is planning that and has expressed support for campaign aides in recent days, a person close to him said. He has asked why Harris is raising so much more money than him, people familiar with the comments say. Trump has also repeatedly raised the large crowds that Harris is getting compared with Biden, people who have spoken to him said.

Some Trump advisers grew alarmed last week when Kellyanne Conway arrived at his Bedminster, N.J., golf resort for a meeting and posted about it on X. Conway, who was the manager of his winning campaign in 2016, has a long relationship with Trump and has questioned some of the campaign’s decisions but has not specified any personnel changes she thinks Trump should make, according to people who have spoken to her.

“The Kamala bump was a direct cause from the Biden slump,” Conway said in an interview. “There was nowhere for his successor to go but up in fundraising and enthusiasm. But this remains President Trump’s election to lose. The electoral map and underlying fundamentals favor him.”

While accepting the Republican nomination at the convention, in his first speech since the shooting, advisers wanted him to give a sober and hopeful address about the future. He began by telling an emotional tale of his shooting but wandered off the teleprompter remarks dozens of times, stretching the speech “past the point where it was productive,” a campaign official said. Inside the arena, loyal attendees could be heard grumbling as they exited about how long the speech was. Several people close to Trump described it as a missed opportunity.

Inside his campaign, there have been frustrations about some of his other comments, people close to Trump say. When he went to a National Association of Black Journalists event in Chicago, he made unplanned remarks that suggested Harris was not really Black.

“I didn’t know she was Black until a number of years ago when she happened to turn Black and now she wants to be known as Black. So, I don’t know, is she Indian or is she Black?” Trump said falsely.

While the campaign sought to defend his comments, Trump was frustrated by the event. He did not know that Harris was not going to appear, that the journalists were going to ask such tough questions and that there would be a fact-checking component to the event, one person who spoke with him about it said.

His team has sought to attack her on policy grounds while casting her as unfit. They have pushed arguments about rising numbers of undocumented immigrants crossing the southern border, inflation that rose while she was vice president, her record as a California politician and her comments backing certain liberal positions in the past, such as supporting the Green New Deal.

At his rally in Atlanta this weekend, Trump veered way off-script to attack Brian Kemp, a popular Georgia governor who would not seek to overturn the 2020 election for him. He spent a large portion of his comments slashing Kemp, who previously had considered appearing with the former president this fall. In the days after, Kemp’s team have not heard from Trump’s campaign, even as some outside advisers have sought a détente.

Erick Erickson, a conservative Georgia radio show host, said he was flooded with calls from suburban voters who were angry with Trump’s attacks on Kemp. Ericksen said he still believed Trump will probably win Georgia.

“All attacking Kemp does is remind people why they didn’t like him,” he said. “He makes it closer than it should be. That’s the problem. You’re not going to have Kemp on the campaign trail for him, which you could have had.”

Cheung, the Trump spokesman, dismissed concerns expressed by allies about the campaign and its messaging. “Our message discipline is second to none,” he said. “It’s why President Trump was able to take out Joe Biden in the debate, it’s why we’ve been so successful thus far, and it’ll be why President Trump will win the election.”

Several people close to the campaign said there was an ongoing effort to get Trump to focus on attacking Harris and slashing Democrats. Trump enjoyed an advantage of two percentage points over Biden in a Washington Post average of national polls taken in July, before the president bowed out. Harris is polling four percentage points ahead of Biden’s number in a Post average of national polls since then, giving her a one-point edge over Trump.

“This is really Trump’s race to lose,” Graham said. “I hope we’ll get more focused on prosecuting the case against her. I think he was frustrated originally, but over the last couple days, we’ve had good conversations and I think we have the wind at our back.”

A Tuesday afternoon post from Trump on his Truth Social media site – which included a number of nicknames, falsehoods and baseless accusations – suggested he was still steaming.

“What are the chances that Crooked Joe Biden, the WORST President in the history of the U.S., whose Presidency was Unconstitutionally STOLEN from him by Kamabla, Barrack HUSSEIN Obama, Crazy Nancy Pelosi, Shifty Adam Schiff, Cryin’ Chuck Schumer, and others on the Lunatic Left, CRASHES the Democrat National Convention and tries to take back the Nomination, beginning with challenging me to another DEBATE,” the post read. “He feels that he made a historically tragic mistake by handing over the U.S. Presidency, a COUP, to the people in the World he most hates, and he wants it back, NOW!!!”