The dismissals, following his comments calling Mexican immigrants "rapists," among other unpleasant epithets, came in waves for the former star of reality TV's The Apprentice.
Spanish-language broadcaster Univision dropped Trump's Miss USA pageant from its schedule. Mexican media giant Grupo Televisa withdrew from his Miss Universe competition. NBCUniversal sacked him. Macy's department stores dumped his clothing line. Even Houston hair-care line Farouk Systems cut off all deals with the billionaire real-estate magnate and would-be politician.
But as much as The Donald's incendiary remarks burned his business bridges, they may have also fired up his base of red-meat Republicans.
Trump is still going strong in conservative polls.
In fact, he has moved into second place in the early decision states for the Republican nomination, New Hampshire and Iowa, according to the most recent surveys.
"His numbers only appear to be going up," says former Republican strategist Roger Stone, now a Tea Party member who supports Trump.
"Donald Trump's sin is he said some comments that were politically incorrect. But politically incorrect is not the same thing as unpopular, depending on what segment of the population you're talking to."
Those comments — part of Trump's rambling, unscripted declaration for his Republican candidacy last month — included allusions to Mexican immigrants as drug-pushers and criminals.
"They're bringing drugs, they're bringing crime. They're rapists," Trump said in the lobby of New York's Trump Tower, drawing guffaws from the press corps.
"Some, I assume, are good people," he added.
Hispanic groups slammed the remarks as derogatory. (Actress Eva Longoria even compared him to Hitler.)
And some of his biggest clients rushed to distance themselves from the candidate by ending their business relationships.
Right-leaning Americans were more forgiving, however.
The latest Iowa polling numbers from CNN put Trump in second place among a crowded field of Republican contenders, tying with retired neurosurgeon Ben Carson for 18 per cent of the vote, and just behind front-runner Jeb Bush.
It was an impressive repeat performance of sorts, following a New Hampshire survey that showed Trump was besting everybody except for Bush for Republicans' choice for nominee in 2016.
As for Trump's business interests taking a hit, Stone notes that the Trump fortune runs much deeper than a few product-line endorsements and TV deals.
"He's worth just under $10 billion. Do you really think he gives a s--t about Macy's?" he said.
Philip Ammerman, managing partner of Navigator Consulting Group, said it's worth remembering the main part of Trump's fortunes still lies in property.
Ammerman also wonders to what extent Trump is being deliberately provocative, adding that he can't imagine a candidate would run for president and willingly alienate the Latino vote.
"It's just bad policy to make comments like that, quite apart from the fact that it's just entirely, ethically wrong," he said.
"I think it's crazy if you're a presidential candidate to deliberately alienate and offend, what, 20-25 per cent of the U.S. population?"
Gwenda Blair, author of Donald Trump: Master Apprentice and The Trumps, said the outspoken business magnate must have known that he would have to deal with some fallout to his corporate interests during his pursuit of the Oval Office.
After all, he had already gained notoriety for driving the fringe "birthers" conspiracy that questioned U.S. President Barack Obama's citizenship in 2011.
"He got a lot of traction out of birther claims, and this newest anti-immigrant rhetoric is just taking it to the next level," Blair said. "He is a really shrewd guy, and I would guess his calculus expected the current blowback."
Trump, perhaps the first presidential candidate with his own fragrance line ("Success by Trump" is billed as a scent that "captures the spirit of the driven man"), takes immense pride in his business empire, and claims a net worth of around $9 billion US.
And so his continued campaigning, despite losing lucrative business deals, could be an attempt to signify that he's really in the race to win.
"I definitely think he's being taken much more seriously this time than any other time he's threatened to run, or mulled running," says Sue Zoldak, the Washington-based vice-president of the public-relations firm Levick.
But Zoldak, who specializes in public affairs and crisis reputation PR, said it appears so far that Trump has failed to capitalize on his time at the bullhorn.
When NBC ended their business relationship with him, he blasted them as "weak and foolish," took a swipe at the network's former anchorman as "lying Brian Williams," and threatened to sue. He also threatened legal action against Univision for nixing the Miss USA deal.
"Donald Trump has mastered the zinger. He's got a lot of media attention for his response," Zoldak said.
"But if he's to move forward and be considered a serious presidential candidate, he needs to pivot these opportunities to talk to the media about issues and stances for the country. He's missing out on these opportunities."
Never back down
Unlike on his reality TV show The Apprentice, Zoldak said, one-liners can only take a politician so far.
"He really has to demonstrate that he can understand policies. He can't just come into the boardroom, make a zinger and walk out," she said.
If there is a red line for Trump, it may have nothing to do with his personal fortunes.
Macy's did not discontinue the fashion line belonging to his daughter, Ivanka.
But Zoldak believes that any harm done to his children's businesses could force him to backpedal on controversial statements.
For his part, Stone can't see that happening in any scenario.
"Donald Trump never backs down," Stone said.
"It's part of what people admire about him. But back down? Issue an apology? Never," he said. "That's not the Donald Trump I know."