A trio of fratty-looking bros doing a keg stand was probably the last thing you’d have expected to see in an advertisement highlighting the Affordable Care Act’s benefits on the eve of its rollout last year. That is, unless you knew the ad was the work of ProgressNow Colorado, which has been jolting the state’s political landscape with the unexpected for just over a decade. The poster-style “Got Insurance?” ads, which cost just a few hundred bucks to produce, have gotten thousands of hits on YouTube and sparked heated debate on talk radio, cable television, The Daily Show, Facebook, and Twitter.

After “Brosurance” came “Hosurance” (both monikers arose courtesy of social media), another round of equally eyebrow-raising ads targeting women. One, featuring a young man and woman, was captioned in her voice: “OMG, he’s hot! Let’s hope he’s as easy to get as this birth control”—which, the ad notes, is now free thanks to Obamacare. As earned media goes, the campaign was pure gold. But apart from the chatter the ads generated, did they actually do anything—such as increase ACA enrollment?

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It’s difficult to say. ProgressNow officials insist the campaign was a success because it made young people across the country more aware of their new health insurance options. But it also triggered predictable backlash: Republicans seized on the ads as evidence that Democrats weren’t serious about the real problems resulting from October’s rollout of new online insurance marketplaces: sticker shock, unexpected cancellations or renewal requirements, and technical glitches. “It turned the entire Obamacare scheme into the joke that it actually was,” says Kelly Maher, whose group Compass Colorado was created as a conservative counterweight to the progressive media machine. Even some Democrats, increasingly nervous about the public’s growing concerns about the new law, grumbled about the ad campaign. Says Jason Bane, founder of the left-leaning blog Colorado Pols, “I thought they were a little silly, but they were supposed to be.”

Michael Huttner started ProgressNow as the Rocky Mountain Progressive Network in 2003—the name was changed in 2005—partly to counter the libertarian Independence Institute. It was one component of a new progressive infrastructure funded by a few wealthy Colorado liberals who quickly helped paint a formerly red state purple and then blue, and its success has made it a nationwide
blueprint for political engineering. Early on, Huttner compiled email addresses and performed publicity stunts, memorably having a friend dress up as a neon green pea pod in 2008 to welcome Senator John McCain to Denver. (Translation: The GOP presidential hopeful and President George W. Bush were “two peas in a pod.”)

Huttner now helps start ProgressNow chapters around the United States. But what was revolutionary in 2003—using email lists to reach a party’s activist base, employing technology and creativity at the grassroots level to affect messaging and news coverage, and maintaining permanent operations instead of closing up shop after each campaign—has become commonplace today.

Republicans have mimicked the ProgressNow model with their own 501(c)(3) organizations, email lists, conservative blogs, and attack machines. Relying heavily on humor in political messaging—“snark” may be more accurate—is now routine, although it’s also becoming increasingly difficult given the lack of mirth in our political discourse. The past decade of Democratic political dominance in Colorado only makes ProgressNow’s mission more difficult—or at least less cheeky.

“After we won in 2004, we asked ourselves, What do we need to keep on winning?” says Ted Trimpa, who’s chaired the ProgressNow board since 2008. “And we needed someone out there pounding away all the time, going after politicians who oppose progressive policies and giving the supporters of those policies room to move. We built ProgressNow to do that, and to give our base a voice.” But after the Brosurance kerfuffle, Democrats and Republicans alike pondered whether ProgressNow had lost its touch, and even its supporters began to wonder how an organization that was so ahead of its time a decade earlier could continue to be effective.

In the back of an old Victorian house just off 17th Avenue, the two staffers who have primarily run ProgressNow Colorado since its inception begin their workdays sitting in front of silver MacBooks on a sturdy wooden dining table, scanning emails and tweets and chatting about the latest news. Alan Franklin, whose long gray hair and glasses would have looked at home in 1970s San Francisco, sips coffee out of a “Thanks Obamacare” mug, a merry prankster preparing for his day. To his left is Jen Caltrider, a former CNN producer and the mind behind many of the organization’s campaigns. Dubbed “the lesbian MacGyver” by her former boss, Bobby Clark, she is the yin to Franklin’s yang, as understated and wry as he is bombastic and combative. She created the now widely used #COleg hashtag on Twitter in 2011 as a way to aggregate news and information about the legislative session. Franklin is the strident voice who often dominates that feed, quick to push the progressive message and eager to tangle with conservatives. “Alan is a paid troll,” says Maher, herself a paid conservative troll of sorts who has repeatedly blocked Franklin on Twitter.

Franklin and Caltrider have long been an effective pair: Caltrider conceives the ideas, and Franklin defends them. Among her early successes—the one that earned her the MacGyver nickname—was a series of videos supporting Referendum C, the 2005 measure that allowed the state to keep a tax surplus that otherwise would have been refunded to taxpayers under TABOR. The videos, produced for about $50, showed Coloradans forced to fill potholes and fight forest fires themselves as a result of potential budget cuts, should Ref C be voted down. Even though YouTube hadn’t been widely launched yet, the videos got 50,000 views, and the referendum passed.

Other ProgressNow campaigns have faced more resistance—often from squeamish Democrats. When they recognized the need to turn the pejorative term “Obamacare” into a positive in 2011, their proposed “Thanks Obamacare” campaign drew the attention of Jim Messina, a close adviser to the president. “Our funding was even threatened,” Franklin says. “These people came out of the woodwork to tell us our message was single-handedly going to destroy the Affordable Care Act.” The ad campaign went ahead, and within about six months the president himself began using “Obamacare” on the stump. “We never hear, ‘You’re right,’?” Caltrider says. “But we often hear later on, ‘You were right.’ That’s partly our fault because we’re weird. We don’t have the best social skills. But we’re blunt and honest.”

The “Got Insurance?” campaign did resonate with certain audiences. “We had clinics in New York, colleges in Oregon, all asking us for high-resolution images of the ads they could put up,” Caltrider says. “There was a group of students at Bates College in Maine who dressed up as the Brosurance guys for Halloween.” Although she says she expected that, she’s still surprised about the angry backlash. “I didn’t know keg stands were going to piss people off,” she says. “I don’t drink. And I’m a lesbian, so I don’t use birth control, either.” After it went viral, Franklin was tasked with defending the campaign on social media sites. “I was the second most mentioned person on Twitter,” he boasts. “Right behind Snooki.”

Unfortunately, Dems who were fending off negative stories about policy cancellations and rising premiums didn’t appreciate the intended humor. Nor did certain pundits. “Perhaps funders of [ProgressNow] may want to ask some questions as to how their monies are spent,” political analyst Eric Sondermann posted on Facebook after the ads were released. (Franklin responded by tweeting that Sondermann is a “feckless clown.”)

Franklin’s Twitter bio reads, in part: “My bosses know I am kind of a loose cannon already, so whatever.” But does that whatever actually matter? As social media has become more pervasive, Franklin’s role has changed. “We are in the middle of a protracted ideological battle with the right wing, and the consequence of that is heated discussion,” he says. “I relish that.” In this humorless, polarized climate, the lasting impact of Twitter wars varies. And over time, a constantly combative online presence may be changing how some people view the organizations behind the inflammatory messages. “The jury’s still out,” Trimpa says, “on how effective being really aggressive in the Twitter space actually is.”

After a strong 10-year run, 2013 revealed the limitations of ProgressNow Colorado’s power, as well as that of urban Democratic majorities driving progressive policies in a complex, diverse state whose voters are starting to wonder if the left has overreached. ProgressNow Colorado was only tangentially involved with the Amendment 66 campaign (which would have raised $950 billion in new taxes to benefit schools) and with defending two state senators who were eventually recalled over their support for new gun laws, but it still couldn’t soften the ground enough to help Democrats avoid devastating losses on both fronts.

ProgressNow’s two kindred spirits would not agree with the contention that their influence might be waning. Franklin says the local media too often fails to distill truth from fiction, especially on the gun control bills that sparked an unexpected backlash. Caltrider blames an overly cautious progressive wing of the Democratic party. “What happened with gun control is exactly what we did with Obamacare in 2009,” she says. “We passed something that was a necessary policy change, and then we hid from it.” During the recall campaigns, Democrats ran timid messaging that avoided the very issue—gun control—that was invigorating their opposition. Meanwhile, the “Yes on 66” publicity tiptoed around the proposed income tax hike, highlighting only the potential benefits for students in a series of sweet but insipid TV ads. “ProgressNow can make people a little uncomfortable sometimes,” Caltrider says. “But we’re willing to say and do the things that other people are not.”

ProgressNow Colorado faces a more target-rich environment in this midterm election year, and the group has drawn blood from anti-progressive candidates in seemingly every recent cycle. Sometimes, as with Bob Beauprez’s gubernatorial campaign in 2006, it’s day-by-day; at other times, it comes all at once, as with Scott McInnis in 2010, when progressives unearthed a plagiarism scandal that blew up the GOP front-runner’s campaign.

But returning to offense—Franklin, especially, says he can’t wait to dust off his many thick binders of research on Beauprez, who’s again running for governor—doesn’t guarantee new attacks will resonate, especially with an electorate that’s gotten used to, if not weary of, the ProgressNow approach. In April, the group staged a press conference at the Capitol that featured a rented boat with a cardboard cutout of GOP senatorial candidate Cory Gardner aboard. (It was meant to highlight a junket to Florida Gardner took with Republican donors in 2012.) Only a handful of reporters showed up. “We’ve come to a place where the low-hanging fruit is gone because we’ve had a lot of success,” says Amy Runyon-Harms, the group’s executive director since May 2013. “The work just gets tougher.”

Even Trimpa, whose sway with donors has given ProgressNow room to operate, acknowledges that a decade of perpetual political trench warfare has created a more challenging environment for his soldiers. “You have to maintain some level of believability,” he says. “It’s a fine line between doing things to get attention and being taken seriously. Once you’ve crossed that line too many times, you’ve lost your public credibility. Then you’re done.”