Donald Trump. Jeff Swensen/Getty Images

Disaster might be too light of a term to describe the recent stretch of days in Donald Trump's quest for the presidency.

Over the course of two weeks, Trump has: lambasted a federal judge over his Mexican heritage; delivered highly controversial and oft-condemned responses to the horrific Orlando terror attack; fired his campaign manager; and, through it all, watched as both his poll numbers plummeted and his fundraising hit an unprecedented low.

Not ideal.

"This was inevitable in a sense, because it is Trump being Trump," Tim Miller, who served as Jeb Bush's communications director during his 2016 presidential run, told Business Insider. "And I think a lot of pundits, including the Trump campaign, completely misunderstood that the nature of the general electorate is so different from the Republican primary electorate - that, you know, the same old Trump shtick wasn't going to work.

"This was extremely predictable," he said. "The general electorate was increasingly turned off by him even as he was winning primary elections. I don't like to give credence to the idea that he was making some sort of strategic communications calculation. He wasn't. He was just being Trump. This is Trump au naturel."

Trump will again attempt to somewhat reset his campaign Wednesday, when he will deliver a major speech targeting his rival, presumptive Democratic nominee Hillary Clinton, in New York. He will attempt to put the focus on Clinton and turn it away from a tumultuous few weeks.

Trump's tailspin began to gain speed when he pressed on for days at the start of June about how US District Judge Gonzalo Curiel could not fairly preside over a civil case involving his for-profit real-estate school, Trump University, because he is of Mexican heritage and Trump is planning on "building a wall" along the US-Mexico border.

REUTERS/Nancy Wiechec

Curiel was born in Indiana. Republicans from all sides of the party, in addition to many on the outside, condemned the attacks. It was Trump's first real intraparty self-fueled firestorm since he clinched the nomination in early May.

From there, his response to the Orlando terror attack was of great concern to many. Just hours after the attack, Trump responded on Twitter.

"Appreciate the congrats for being right on radical Islamic terrorism," he wrote. "I don't want congrats, I want toughness & vigilance. We must be smart!"

His poll numbers soon plummeted. He went from taking a very narrow lead over Clinton to dipping about six points behind her in the RealClearPolitics average of several polls. Even worse, a recent Bloomberg poll found that 55% of respondents said they'd "never" vote for Trump, while a CNN poll found that 48% of self-identified Republican and Republican-leaning voters said they wanted the GOP to select a different nominee.

Realizing that the tide was really turning against him, Trump made a big move: He ousted campaign manager Corey Lewandowski on Monday in hopes of changing the direction of his fledgling campaign. That came just hours before a devastating campaign finance report was released, showing that Trump raised just about $3 million in May and ended the month with $1.3 million in cash on hand. Compare that with Clinton, who raised roughly $28 million in the month and ended it with nearly $42.5 million in cash on hand.

To put Trump's fundraising in perspective: The amount of cash he has on hand at the moment is comparable to some US representatives and candidates running to either retain or take over a House seat.

AP Photo/John Locher, File

Rick Hasen, a professor at the University of California at Irvine who specializes in campaign finance regulation and election law, told Business Insider that he's never seen such a dismal report on the presidential level.

"We've never seen this kind of disparity between the presumptive nominees of the two parties," he told Business Insider. "It's still possible that Trump will be able to turn it around. But he's going in at a very big disadvantage."

Miller called the report a "monumental disaster."

"There are so many elements of it that are terrible," he said. "Sometimes it's hard to focus on one or two things - that's sort of a metaphor for Trump's whole campaign, as a matter of fact."

He added that even Trump's claim that he's running a fiscally conservative campaign was proved false by the report.

"Trump managed to spend more than he took in in May, without doing any voter contact, without doing any advertising, and without doing any data analytics," he said. "What was he spending the money on? He spent it on overhead for his events, and he spent it on visits to events at Trump properties. Not only has he not raised any money, but the money he is raising is not going to anything that's productive toward winning a general election. It's just a complete farce."

Ralph Freso/Getty Images

Alex Conant, a Republican strategist who worked as Marco Rubio's communications director during his 2016 presidential bid, told Business Insider that being in the red in May is "unheard of in presidential politics."

"On the current trajectory, he'll run out of money well before Election Day," he said. "Running for president is a very expensive proposition. And if he's not prepared to spend hundreds of millions of dollars on his own, he needs to build a giant finance network. And he's falling way behind schedule."

Pundits have pondered for months whether Trump will "pivot" to being a general-election candidate - and it now looks as if he's taking that idea more seriously than ever. But it's no guarantee.

"No, no, he's not going to pivot," Miller said. "He's not capable of pivoting."

"You know, I joked the other day [about] the old saying - fool me once, shame on you, fool me twice, shame on me," he said. "Trump has fooled some people, like, about 17,000 times, and they're still wanting to be fooled."

He said some people are just "wishing and hoping for it to happen."

"Even if they put him on a teleprompter for one speech [Wednesday] - you know, when he's on the teleprompter he looks like a child who got in trouble at school and his mom or his teacher took the dirty words out of his school presentation - he doesn't enjoy that," he said. "And, by the way, it's not going to work."

REUTERS/Chris Aluka Berry

But with bottoming out comes the chance at a rebound - and Trump has made some of the most significant changes to his campaign yet. With Lewandowski out, Paul Manafort, another top aide, acquired more power. So far, that's led to the launch of the Trump campaign's rapid-response team, a big fundraising push, and many new hires.

Trump himself told "Fox and Friends" on Tuesday that the campaign is going in a "different direction."

"We have a group of people, and it's a little bit different," he said. "We're going to be running a little bit different campaign. At the same time, I will say this: We want to keep it lean. I'm not looking to spend all this money. I hear people spend a billion dollars. How do you spend a billion dollars? it's impossible."

Hasen, however, said the fundraising efforts have to increase immediately.

"The number of fundraising emails has to increase. The number of fundraising events has to increase," he said. "The fundraising staff has to be grown so that it can do its job. One [problem] is he doesn't have the apparatus, another is he isn't doing the asking, and a third is it isn't clear how receptive people will be to giving him money. So that's the other question. Even if he tries, how successful will he be?"

Conant said Trump appears to recognize that by continuing the path he's on, he would lose to Clinton by even bigger margins than the polls currently show - hence the campaign shakeup and change of direction.

"But I don't think personnel issues were the reason for his recent drop in the polls, or the fact that Republicans have not united behind his candidacy," he said. "He doesn't just have organizational problems."

The problems, he said, are "much deeper than any one person."

Conant quickly corrected himself.

"Much deeper than any one staffer," he said.