Rep. Dan Lipinski (D-IL) has spent his career sticking his fingers in the eyes of progressives, vocally bucking his party on everything from abortion to Obamacare to gay rights, with few repercussions. In less than a month, they have their first real chance to strike back.

The congressman has long been able to get away with a laundry list of conservative votes in his seven terms in Congress and has avoided a real primary challenge for years, aided by close ties to Chicago’s powerful old-school Democratic machine.

But in the year of red-hot Democratic activism, the #MeToo movement and brutal urban and suburban backlash against President Trump , those old-guard powers are facing a reckoning. And just weeks ahead of Illinois’ March 20 primary, the congressman is coping with perhaps his biggest political threat since his father, longtime Rep. Bill Lipinski (D-IL), retired and anointed him his successor in 2004.

Marie Newman, a former advertising executive, anti-bullying and gun control advocate is gunning for his seat — and has won a number of endorsements from heavy-hitting liberal groups.

“There is a definite path to victory for her, where in past primaries I haven’t really seen that materialize. I think this is a good year in that district for a real Democrat, and a woman. This is going to be a very good year for women,” said Rep. Jan Schakowsky (D-IL), who endorsed Newman in what she told TPM is the first time she’s ever campaigned against another sitting Democratic congressman. “There’s this sense of unity, of being off the sidelines, in the fray, going to vote, and all of that significantly plays into the energy around her candidacy.”

The younger Lipinski has followed in his father’s footsteps in carving a fairly conservative record, especially on social issues. A co-chairman of the fiscally conservative Blue Dog Coalition, he’s one of only three remaining House Democrats who voted against the Affordable Care Act. He’s regularly stood against legislation backed by gay rights groups, long opposed gay marriage and is one of the only House Democrats who opposes the Equality Act, a bill that would offer LGBTQ Americans protections against discrimination in housing and employment. He supported the war in Iraq, has regularly voted against keeping House Minority Leader Nancy Pelosi (D-CA) as party leader, and only recently switched to supporting the DREAM Act. He also recently had to walk back comments opposing unions’ long-sought push for a $15 minimum wage.

But his biggest and most vocal apostasy to liberals has been his steadfast opposition to abortion. A devout Catholic, he’s long served as the co-chairman of the Pro-Life Caucus and has regularly voted with Republicans to defund Planned Parenthood and ban most legal abortion.

Liberal organizations have fumed for years over his votes and views, especially since he holds a district that both Hillary Clinton and President Obama carried by roughly 15 points. But Lipinski easily defeated early primary challengers with the support of one of the country’s few remaining powerful Democratic machines. Party boss and Illinois House Speaker Mike Madigan (D) then gifted him a personalized gerrymander that stretched the 3rd District from his and Lipinski’s base in Chicago’s South Side into whiter, more socially conservative southwestern suburbs after 2010, possibly at the expense of drawing another gerrymandered Democratic district. He hasn’t faced a real challenge since.

But Newman has shown herself to be a capable candidate, with decent if less-than-dazzling fundraising figures, and she has the backing of some of the left’s most powerful groups. She has support from the pro-abortion rights NARAL Pro-Choice America, EMILY’s List and Planned Parenthood Action Fund, MoveOn.org, and the Service Employees International Union, as well as Schakowsky, Rep. Luis Gutierrez (D-IL) and Sen. Kirsten Gillibrand (D-NY).

“The Lipinski monarchy supported by the Chicago machine has continued because nobody’s had the time or resources to do this,” Newman told TPM last week. “We’ve had 36 years of Lipinskis, and everyone’s pretty clear they’re completely out of touch with the district.”

In recent days, outside groups said they’d put their money where their mouths are with a combined $1 million in TV, digital and print advertising attacking Lipinski’s record on social issues, Obamacare and immigration and tying him to President Trump.

“You can’t fight Trump when you agree with him. It’s time for Dan Lipinski to go,” both of the groups’ ads conclude.

Newman needs that help: She had just $237,000 in the bank as of Jan. 1 to his $1.65 million war chest, not enough by itself to give him a serious challenge in a district that’s squarely within Chicago’s expensive media market.

Even with all the groups gunning for him, Lipinski doesn’t seem to think he’s in much trouble in the safely Democratic district.

“I’m not sure why anyone believes this is going to be a close race to begin with,” he told TPM in a phone interview last week, pointing to an internal poll conducted for his campaign in late January that had him up by more than 30 points.

Lipinski acknowledged that the progressive base is spoiling for a fight with the president, and was quick to tout votes against Obamacare repeal and the GOP tax plan, his longtime support for gun control, environmental protections and his endorsement from the AFL-CIO. But he argued that Democrats shouldn’t cast out moderates like himself.

“It’s understandable that people are as incensed by Trump as I am, the things he has done and said. It’s important, though, that we do not form a Tea Party of the left, I think that’s detrimental to the party,” he said. “We’re in a position where we’re down 24 seats in the House, we’ve lost 1000 seats across the country since 2010, and we need to make sure we’re a big tent party, not closing down. That’s not good.”

Lipinski largely ignored Newman’s repeated barbs Wednesday night during their only scheduled debate, only firing back when she criticized his views on gay rights and abortion.

“Religious freedom is under attack,” he warned, saying he now accepts gay marriage as the “law of the land” but arguing that churches and religious organizations shouldn’t be forced to honor it or pay for contraception.

But the congressman does seem to be acting a bit skittish as of late. He called for nonpartisan redistricting during the debate, which Newman was quick to point out for its hypocrisy given his earlier gerrymandering. His reversal on the DREAM Act is a sign he knows the position is untenable in a district with a fast-growing Hispanic population. And while he hasn’t shied away from defending his pro-life views during the campaign, he backed out of a scheduled speech at the national March for Life last month at the last minute.

“I did not want to be up onstage with Donald Trump speaking,” he said. “But a lot of the issues we’re voting on when it comes to abortion are things the majority of Americans, even the majority of Democrats agree with – the Born Alive Infant Protection Act we voted on in January, even the ban on abortion at 20 weeks, national polls show there’s a majority of Democrats who support that. It’s my opponent who has the radical position on this.”

He’s also looked to bolster his standing as with women in recent months. Lipinski’s State of the Union guest this year was Faith Ann Rys, a clinical therapist who treats female victims of sexual assault. Even as he spoke at the Chicago March for Life last month, he worked in a nod to the #MeToo movement.

“We have heard so many stories over the last year. They’ve been horrible stories about assault, harassment, and terrible mistreatment of women. And when this happens it scars all of us. We all, everyone needs to stand up for the dignity of every single individual, every single woman, man, and especially the most vulnerable, the child in the womb. That is what we do everyday int he pro-life movement,” he said onstage.

That effort was a dealt a blow in recent days, however. Madigan has become embroiled in his own scandal, accused of protecting a number of longtime aides who harassed female staffers, and Lipinski was just about the only Democrat who stood up to defend his old friend.

Most local Democrats think Lipinski still has the edge in the contest, where the primary winner will face an avowed Neo-Nazi in the general election. But they think Newman’s chances look better every day. And if she doesn’t pull off an upset this time around, they hope she’ll take another shot next election.

“Although I think she has a wonderful opportunity now, laying the groundwork for 2020 is wonderful,” said Gutierrez.