Washington CNN  — 

It took President Donald Trump less than two minutes to reach for the word “nasty” as he reacted to California Sen. Kamala Harris’ historic selection as the first Black woman to join a major-party ticket.

A few minutes later, the President added “meanest” and “most horrible” to his characterization of Harris and claimed she was “disrespectful” in her attacks on Biden during the Democratic primary, when they stood on the debate stage as equals.

The insults all played into racist and sexist stereotypes about Black women and made clear that Trump does not intend to throw away a playbook filled with misogynistic attacks and dog-whistle racism that have imbued his political career, even as the Biden campaign advances a barrier-breaking ticket.

Trump’s limited political career has brought him up against only one previous Democratic rival, Hillary Clinton, whom he called a “nasty woman” during a presidential debate. And since taking office, Trump hasn’t moderated his tone, digging into a public persona that recoils from political correctness while embracing the divisiveness he believes thrills his supporters and provides them validation.

Facing his first question on Harris during a White House news conference, Trump seemed unfamiliar with the line of attack his campaign had prepared to use on her – and that he had tweeted himself only a few minutes earlier.

“You had an ad out that said she was phony and I wanted to drill down,” a reporter asked before Trump interrupted: “That she was a what?”

Looking down, Trump tried to tick through a list of talking points etched before him in black Sharpie: “She’s very big into raising taxes, she wants to slash funds for our military at a level that nobody would ever believe, she’s against fracking … ”

But he quickly veered away from the staid talking points, shooting instead from the hip and calling her “extraordinarily nasty.”

While the President claimed Harris was his “No. 1 draft pick,” his attacks and the apparent deficiency of the issue-focused talking points revealed a President and his team who would have preferred Biden pick just about any other vice presidential nominee.

It also put into sharp relief the challenge inherent for Trump in lining up against a Black woman on the Democratic ticket at the same time as he tries to win back moderate suburban women turned off by his divisive rhetoric.

Harris was one candidate that several Trump campaign advisers said they did not want, according to two sources familiar with the discussions. Several Trump campaign advisers told CNN they would have preferred to see Biden pick from the other finalists on his shortlist, with a preference for former national security adviser Susan Rice and Rep. Karen Bass, both viewed as lightning rods for controversy.

“She is certainly formidable,” a source close to the campaign said. “She will inject some much-needed energy into the campaign.”

The advisers fear the attacks risk distracting from the Trump campaign’s official strategy and highlighting the President’s history of racist and sexist rhetoric at a moment when he is desperately trying to win back voters turned off by those very attributes.

Others close to the President’s reelection bid insist he is fully prepared to take on a ticket that includes Harris, who had long been considered one of the likeliest running mate options – even if Trump himself appeared both subdued and unprepared when responding to the pick on Tuesday.

A strong contender

When Harris mounted her own bid for the Democratic nomination last year, Trump told advisers he thought she was a strong candidate who would pose a real challenge to Biden, people familiar with the conversations said. He stated recently that Harris would make a “fine choice” as Biden’s running mate.

And along with his daughter Ivanka, he donated thousands of dollars to Harris’ campaigns for attorney general between 2011 and 2013 – after he’d largely stopped contributing to Democrats.

Others in Trump’s orbit pushed back on the notion that Harris would prove difficult for Trump to counter, with a senior Trump campaign aide arguing Harris’ high-energy persona would “show up Biden and make him look weak,” amplifying Trump’s attacks questioning Biden’s fitness to serve as President.

“Would I have preferred actual communist Karen Bass? Sure,” one Trump campaign adviser said, hyperbolically. “But this isn’t that much harder.”

Still, the challenges are clear as the campaign enters a new phase and as Trump and his team take stock of a reshaped contest that polls currently show him losing.

Harris is widely viewed as a center-left politician who has faced criticism from the left-wing of the Democratic Party for being insufficiently progressive, complicating the Trump campaign’s efforts to paint Biden and his vice presidential pick as members of the “radical left.”

A senior adviser close to the President’s reelection effort predicted that his team will have a difficult time shaping Harris in the eyes of voters. By her nature, she is a historic pick who impressed voters on the campaign trail. Clips of her grilling Attorney General William Barr and Supreme Court Justice Brett Kavanaugh as they testified on Capitol Hill have both gone viral.

But most of all, this adviser said, it will be difficult to label Harris as a member of the “radical left” that the Trump campaign has warned will influence Biden if he wins. The attack hasn’t stuck to Biden and some advisers aren’t hopeful it will with Harris either.

That did not stop the Trump campaign from releasing a digital video and statement within minutes of the announcement, accusing Harris of charging left during the Democratic primary and branding her “Phony Kamala.”

Painting a picture

One dilemma the campaign faced immediately Tuesday was whether to portray Harris as an overzealous prosecutor or anti-police leftist. In its first statements on Biden’s pick, the campaign did both.

In a call with reporters later, Trump campaign spokeswoman Katrina Pierson and Tennessee Sen. Marsha Blackburn struggled to differentiate between the competing arguments that Harris is both not tough enough on crime and was overzealous in her prosecution as California’s attorney general.

“What you’re going to see is a lot of security moms that are all across this nation who are going to say, ‘You know what, law and order is important to me and I don’t want a vice president who is out there, marching in the streets with the BLM organization,’” Blackburn said.

Moments later, Pierson called Harris’ record as California attorney general “abysmal” for the exact opposite reason, arguing Harris “fought to keep inmates locked up in overcrowded prisons” and “championed laws that put parents in jail for truancy.”

Later, during an telephone interview on Fox News that was arranged ostensibly so Trump could respond to Biden’s running mate selection, the President repeatedly became waylaid in his attacks on Harris. Even as host Sean Hannity launched a series of leading questions about Harris’ record, Trump quickly reverted to old grievances about Hillary Clinton, the Russia investigation and — his consistent bête noire — windmills.

When he did return to Harris, his attack lines were similar to the grab bag of liberal accusations he lobbed earlier in the day without highly specific nods to her record.

While Trump has never directly faced a Black woman as a political rival, he has repeatedly antagonized lawmakers, mayors, former allies and journalists of color – many of them female – using coded or highly charged language.

He has told Black reporters who are women that they are asking “stupid” questions, described their queries as “racist,” and called one a “loser.” He has repeatedly labeled Rep. Maxine Waters, a California Democrat, as “low IQ” and attacked his former aide Omarosa Manigault Newman as “that dog” and a “crazed, crying lowlife.”

And as racial tensions increased this summer after the murders of unarmed Black Americans, Trump went after Washington, DC, Mayor Murial Bowser, claiming she was constantly asking the federal government for “handouts” while mismanaging the nation’s capital.

Trump did nothing to project a message of racial reconciliation amid the protests; instead, he dug into a “law and order” message that relied heavily on racist themes, including a defense of Confederate statues and the Confederate flag and a reliance on language that harkened to the Civil Rights era.

While Trump believed the approach would enthuse his supporters, polls showed him losing ground among key constituencies who disapproved both of his handling of the coronavirus pandemic and of his racial tensions.

That was particularly true among women – including white women – who said they viewed Trump as unhelpful in improving the parallel crises.

Trump has been working to try and win some of those women back, including by touting efforts to roll back Obama-era anti-segregation rules for the suburbs. In promoting his efforts, he has encouraged the “Housewives of America” to read up on his actions.

CNN’s Betsy Klein, Kaitlan Collins, Jim Acosta and DJ Judd contributed to this report.