In case the weekend had allowed you to forget about the excruciating presidential race that faces the United States this summer and fall, the new ad from Donald Trump will jog your memory about just how nasty it will be:

Is Hillary really protecting women? A video posted by Donald J. Trump (@realdonaldtrump) on May 23, 2016 at 8:27am PDT

The first voice, saying, “I was very nervous,” seems to be Monica Lewinsky. Politico identifies the second as being Kathleen Willey, who accused Bill Clinton of sexual assault in 1993. The final voice is Juanita Broaddrick, who has accused Clinton of raping her in 1978.

Here are a few ways to think through this clip:

Trump is happy to be his own attack dog. Most political campaigns use attack ads, because they work. But most campaigns also keep those ads at arm’s length, because voters say they don’t like them, even as they respond. Candidates would rather not be involved—which is why rules now mandate that voiceover disclosure (“I’m So-and-So, and I approve this message.”) Trump, like his similarly coiffed mustelid doppelgänger the Honey Badger, doesn’t care. Perhaps that’s no surprise, given his string of vicious attacks on everyone from his Republican rivals to Muslims, but it is a shift. Of course, other politicians have been happy to let super PACs do their dirty work. But Trump has no official super PAC—another departure. What’s Trump’s view on whether spouses are fair game? Going after Bill to get Hillary is an interesting gambit. Trump (and his allies) went after Ted Cruz’s wife Heidi, but he later told Robert Draper he’d had second thoughts. “He had come to regret his decision to retweet the Heidi Cruz photo that night at Mar-a-Lago, which had dogged him for weeks now. ‘I could’ve done without it,’ he gruffly acknowledged. ‘Some people were offended.’” Maybe Trump has changed his mind back after a couple of critical stories about Melania Trump and he wants revenge. Or maybe he just thinks Bill is different. Which brings us to our next point ... You’re going to hear a lot about Bill Clinton. The old saying goes that one should attack an opponent’s strengths, not his weaknesses. If so, it would make sense for Trump to go after Bill Clinton, who is one of Hillary Clinton’s most important surrogates. Bill isn’t just her husband and one of the more talented campaigners in memory; he’s also the most popular living president. Going after him is risky, but he has some weaknesses that Trump could exploit—like the womanizing, as well as his recent penchant for going off-script on the stump. All that said, Bill Clinton is apparently spoiling for a fight against Trump, wagering that the sexual allegations are past their political expiration date. “He understands why he's had to bite his tongue about Bernie, but he's looking forward to being able to go after Trump,” a Clinton aide told Jason Zengerle recently. Are the allegations old news, though? Conventional wisdom holds that the various sex scandals around Bill are played out. People know about them, and they either already hate the Clintons or they don’t care. Certainly it is true that in the past, the allegations hurt the Clintons; it is also the case that Bill won two terms in the White House and is well liked today. Maybe Juanita Broaddrick’s case is less well known and more damaging. Certainly, Clinton’s more recent statements that all alleged victims of rape should be taken seriously sit uncomfortably with her long-ago statements about Broaddrick. Or maybe Trump will relearn what Richard Mellon Scaife did years ago: Bill Clinton is Teflon. Can Trump avoid the whiff of hypocrisy and cynicism? Even if the attacks are potent, Trump hardly seems like the best messenger. There’s his own history of misogyny and his ex-wife’s claims of marital rape and there is also, as Conor Friedersdorf points out, his long friendship with the Clintons, which makes his attacks today seem awfully cynical. Could the attacks backfire? The greatest danger for Trump isn’t that these attacks won’t work—it’s that they’ll actually hurt him. His mocking Heidi Cruz only built up sympathy for the Cruz family, as he acknowledged. Meanwhile, the Clintons have often thrived when they're down. Hillary Clinton’s highest moment of popular affection came during the Monica Lewinsky case, while the high point of this campaign so far has been her testimony before the House Benghazi Committee. The question is whether those PR wins were situation-specific, in which case the Clintons might crumble this time. Trump, as usual, is betting that the old rules don’t apply.