I don’t know why I phrased that headline as a question. He’s obviously going to do it no matter what his fans or advisors think. The question, I guess, is whether it’ll help him or hurt him.

It’s not surprising that risk-averse Republicans on the Hill want him to stay far, far away from the subject of Monica Lewinsky. They touched the hot stove of Clinton liaisons in the 90s and got burned. They’ll never touch it again. It’s also a safe bet that Kellyanne Conway and most of the Trump brain trust don’t want him broaching this subject. They’ve spent the past six weeks trying to turn him into a more disciplined, presidential figure. A gutter fight with Clinton, who will claim victimhood in being tarred with her husband’s infidelities, is a risky proposition under those circumstances, especially with women voters. The only people who have Trump’s ear who I thought might egg him on are the pugilists like Gingrich and Christie — but even Newt thinks this is a bad play.

Well, no matter. Sounds like it’s happening.

“Mr. Trump has never treated women the way Hillary Clinton and her husband did when they worked to destroy Bill Clinton’s accusers,” reads one of the talking points the campaign sent to surrogates on Thursday as the controversy surrounding the story of former Miss Universe Alicia Machado continued to dominate headlines of the race.

And during a rally Thursday afternoon in Bedford, N.H., Trump himself referenced the scandals of the 1990s that he’s been congratulating himself for not talking about all week. “The Clintons are the sordid past,” he said. “We will be the very bright and clean future.”

Surrogates are getting into the act too:

Tennessee Rep. Marsha Blackburn brought up Paula Jones, Gennifer Flowers, and Monica Lewinsky in an MSNBC interview. Arkansas Attorney General Leslie Rutledge also said on MSNBC that “If we want to dig back through the ‘90s on comments made about women, we can certainly look to Secretary Clinton referring to Monica Lewinsky as a neurotic loony toon.” And in another MSNBC interview, Rep. Chris Collins also criticized Hillary Clinton for allegedly mistreating the women with whom Bill Clinton cheated. (In correspondence brought to light by the Free Beacon two years ago, Clinton was reported by friend Diane Blair to have referred to Lewinsky as a “narcissistic loony toon” in private.)

Rudy Giuliani has taken the line of attack one step further by referring to Clinton as “too stupid to be president” because of her husband’s affairs.

I don’t think Trump attacking Hillary over Bill is doomed to backfire but it may require a degree of deftness that Trump simply doesn’t possess. The trick is keeping Hillary’s roles as victim and accomplice distinct. It’s stupid to criticize her over the mere fact that Bill is a serial philanderer; all that’ll do is make you look boorish and drum up sympathy for her. If, though, you can make the case that she was complicit in destroying the credibility of women who accused Bill of misconduct, up to and including rape in the case of Juanita Broaddrick, then you’ve got something. That would cut to the heart of Clinton’s “girl power” shtick. Andrew Ferguson does it superbly here. Also, if Trump’s going to do this, Broaddrick has to be the central figure in the case he prosecutes because her accusations are the most gravely serious. If you toss her in as just one character in a field that includes Monica, Paula Jones, Kathleen Willey, Gennifer Flowers, and so on, it’ll muddy the message Trump wants to send. No one (much) cares if an ambitious Hillary tried to keep one of her husband’s girlfriends quiet en route to the White House, but hushing up a rape victim is a different matter. Does Trump have the discipline to stick to blaming Hillary for her own actions rather than Bill’s, and to limit his accusations to Juanita Broaddrick instead of Monica Lewinsky?

Probably not, no, but I think he’s going to attack regardless. Partly that’s because it chaps Trump’s ass, I’m sure, to have Clinton suddenly killing him over sexism towards Alicia Machado when there’s an honest-to-God rape allegation hanging over the Clintons’ heads that the wider media rarely discusses. He fancies himself a counterpuncher (he’s not, he’s really just a puncher) and Billary is begging for a counterpunch right now. Beyond that, I think Trump’s base really, really wants to see him do this whatever the eggheads on their side like Conway and Gingrich might think. Trump is the right’s id, and that id desperately craves bareknuckle warfare with the Clintons whether it’s to their strategic advantage or not. If Trump laid into Hillary onstage over Juanita Broaddrick next week for 60 seconds, Rush Limbaugh would need smelling salts the next morning. The whole appeal of Trump, in fact, is that he’s willing to go places that other Republican politicians won’t because he’s Politically Incorrect and doesn’t give a crap whether the media regards him as gauche because of it. You could argue that the entire reason you’d nominate someone like Trump is because he’s likely to throw Broaddrick and Lewinsky and Jones in Hillary’s face in front of 80 million people when Ted Cruz or Marco Rubio would pass. “He fights,” right? Well, now he gets to prove it.

But don’t forget, Clinton has proved this week that she understands Trump well enough to set a trap for him that’s got him jumping through hoops like a trained tiger. She had to have known that angering him by rubbing his face in the old Machado business would raise the risk of him firing back over Broaddrick et al. And if she’s comfortable enough with that possibility to have sprung the trap with Machado anyway, she either must have something else planned when Trump takes the bait on Bill or she has data that leads her to believe that Trump’s attacks will backfire spectacularly with women — especially when her friends in the media open fire on him in retaliation. But hey, if his sagging polls this week achieve nothing else, maybe they’ll liberate him to undertake higher-risk attacks. If he’s down 12 points in the next poll of Pennsylvania, why not pull the pin and lob the Broaddrick attack at Clinton? Maybe it’ll take Hillary down. And even if it blows up on him, he was already half-dead anyway.

Here’s Rush arguing this morning that Hillary’s the real bully towards women. See what I mean? The right wants this fight! Exit question: What does Trump say when Hillary reminds him that he’s been very sympathetic towards her over Bill’s misbehavior in the past?