A super PAC allied with Hillary Clinton launched a new TV ad Thursday that labels presumptive Republican presidential nominee Donald Trump a “con man” with a string of business failures.

The ad by Priorities USA Action juxtaposed video of Mr. Trump boasting that “I have very successful companies” with examples of his failed businesses, including Trump Mortgages, Trump Airlines, Trump Steaks, Trump Magazine, Trump Vodka, Trump University and Trump Castle Casino Resort in Atlantic City.

“Businessman?” asks the ad.

The 30-second spot ends with script across the screen that reads: “Donald Trump is a con-man.”

The attack is part of a $96 million ad blitz planned by Priorities USA Action to chip away at Mr. Trump’s public persona. The group began airing two ads Wednesday that depict the real-estate tycoon as a sexist and misogynist.

Republican strategists have urged Mr. Trump to quickly respond with his own TV ads in battleground states such as Florida, Ohio, Colorado and Virginia.

Mr. Trump prides himself on his business prowess and claims to have a $10 billion fortune, although some analysis have pegged his fortune at about half that amount.

Mr. Trump filed a personal financial disclosure form this week with the Federal Elections Commission that he said showed a $557 million income.

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