Donald Trump finds himself ensnared in one of  his worst news cycles of the presidential campaign, and it could get worse this week as the presumptive Republican nominee will face his first real fire from the Clinton machine. 

After months of casually deflecting attacks from Republican rivals, Trump is now suddenly on the defensive, fending off questions about whether he impersonated a public-relations agent in the early 1990s, defending his past treatment of women, and trying to explain why he won't make his tax returns public. 

On Wednesday, Priorities USA, a pro-Clinton super-PAC, will begin airing its first television attacks on Trump, and the group is planning to unleash $136 million in advertising against him between now and November.

The first $6 million in ads is scheduled to air in Ohio, Florida, Virginia, and Nevada through June 8, and will later expand to Iowa, New Hampshire and Colorado. 

Lines of fire in the first two ads focuses on Trump’s statements about women.

Coupled with a flurry of other negative stories, the reports and the ads based on them could possibly jeopardize Trump's brand as a man who always tells it like it is. 

“All of these stories matter. They may not turn any of his supporters against him but they inhibit him from growing his support,” said Rob Stutzman, a California-based Republican consultant who was with the anti-Trump movement. “The sum of all these stories paints him as a liar, and confirms the central narrative of the Clinton campaign that he’s a flim-flam man unfit to serve as president of the United States.”

This is Trump’s roughest patch since a series of stumbles cost him the Wisconsin primary after re-tweeting an unflattering picture of a rival’s wife and repeatedly changing his position on abortion. It comes at a time when Trump’s focus has been on the behind-the-scenes work of winning over Republicans on Capitol Hill, rather than driving the narrative for the news cycle with headline-grabbing rallies across the country.

Trump spokeswoman Hope Hicks did not return an e-mail asking for comment. Trump’s aides have brushed off the latest round of negative news, arguing that what actually matters will be how he leverages the national convention, his running-mate selection, fundraising, and how he finesses the transition process.

Part of Trump's genius, some political observers say, is the way that he uses fresh controversies to drown out older ones.