In 1997, Tammy Baldwin had been campaigning hard for U.S. Congress when former Dane County Executive Rick Phelps jumped into the race.

At the time, Phelps was extremely popular — he’d won his last election in a landslide, with 74 percent of the vote. He had so much clout with Democrats that he was being promoted as a challenger to three-term incumbent Gov. Tommy Thompson.

“There was a lot of hubbub around that because he was a very well-known progressive,” says Kate Peyton, who worked as financial director for Baldwin’s congressional campaigns. “He was a very formidable candidate.”

Peyton remembers strategizing at Baldwin’s house on the near east side and saying: “Well Tammy, maybe you want to rethink what you’re doing because it’s going to be tough.

“Our soft-spoken friend looked me right in the eye and asked, ‘Kate. Do you think I should wait my turn?’” says Peyton.

What Baldwin said next has stuck with Peyton for two decades: “In a very steely way Tammy said, ‘I believe that women have to run especially when it’s hard and not wait our turn. We can’t wait until we get a tap on our shoulder or we’ll never get anywhere.’”

Baldwin won the race against Phelps in a four-way Democratic primary. That November, she defeated Republican Josephine Musser to become the very first woman elected to Congress in Wisconsin. It wouldn’t be the first or last time that Baldwin would make history.

Baldwin’s road to the U.S. Senate is littered with the shards of glass ceilings. She was the first openly gay member of the Wisconsin Legislature. The first openly gay member of the U.S. House of Representatives. The first woman to be elected a U.S. senator in Wisconsin. And the first openly gay senator in the nation’s history.

In her 2012 Senate race, Baldwin ended the political career of the once invincible Thompson. For her reelection campaign, Baldwin is championing the dairy industry and college affordability and fighting to preserve what’s left of the Affordable Care Act while pushing for a single-payer system. She’s also raising alarm about threats to Medicare and Social Security, and promising to counter the agendas of out-of-state billionaires.

She’s taking these positions at a time when Wisconsin is starting to be a lonely place for progressives. She’s one of just two statewide elected Democrats left in the state. In 2016, Donald Trump was the first Republican to win a presidential election here in 30 years. Gov. Scott Walker has a higher approval rating than Baldwin. Marquette Law School’s July 18 poll has Walker’s job approval at 47 percent; disapproval was 45 percent. For Baldwin, 41 percent view her favorably; 40 percent unfavorably. However, more voters have no opinion of Baldwin (18 percent) than Walker (7 percent).

On paper, Baldwin seems like an easy mark for conservative groups, which have already spent millions on vicious attack ads against her. She’s a religiously unaffiliated, peace-loving lesbian born and bred in the socialist swamp called Madison.

Yet, Baldwin is more politically astute than many critics realize.

For instance, the senator tells Isthmus, she didn’t let her profound disagreement with Trump on nearly every issue keep her from searching for common ground when she met the president with a group of senators in 2016.

“I decided I wanted to focus on Buy American policies. I figured I could use this opportunity hopefully to advance legislation and see if there was common ground to work on something together,” Baldwin recalls. “He expressed support.”

A year later, while visiting Kenosha, Trump also publicly said he backed Baldwin’s Buy American efforts “100 percent.”

Though GOP leaders in Congress have not moved her legislation, she says she hasn’t “given up hope.”

Voters will decide on Nov. 6 whether Wisconsin’s progressive senator gets another crack at it.

× Expand Brent Nicastro Baldwin was sworn in to the state Assembly in 1993, holding her seat for three terms before being elected to Congress in 1998.

Baldwin has always called Madison home. She attended kindergarten at Shorewood Hills Elementary and was valedictorian at West High in 1980. After studying political science and mathematics at Smith College in Massachusetts, she returned to Madison to attend UW Law School. Baldwin has represented Madison in various ways for more than three decades. One year into law school in 1986, Baldwin served a brief stint on the Common Council; when she was 24, she won a seat on the Dane County Board.

Dave Ripp — the last conservative on the board — is the only supervisor left who served with Baldwin during her four terms. Although he won’t be voting for Baldwin, Ripp says they worked well together.

“Supervisors from the isthmus tend to be harder to work with. But at that point in time, Tammy would work with all sides,” says Ripp. “I sort [supervisors] into the talkers and the doers. She wasn’t one to talk to just hear herself talk — like some. So yeah, she was a doer. We got along fairly well.”

In 1992, Baldwin won a state Assembly seat. Former state Rep. Spencer Black (D-Madison) served with Baldwin and remembers her being “excellent at broadening a coalition.”

“She was good at reaching out and persuading [lawmakers] who wouldn’t fall right into place on an issue. She was able to form genuine relationships with people who were not necessarily inclined to agree with her on most issues,” says Black. “She doesn’t pound a podium and yell. But that doesn’t mean she doesn’t have strong beliefs. People have always underestimated Tammy. But the truth is, she’s very effective.”

During her seven terms representing the 2nd Congressional District, she voted against the USA Patriot Act, criticized the Iraq war and voted against repealing Glass-Steagall, the Depression-era law that kept commercial and investment banking separate for more than half a century. Baldwin has been advocating for a single-payer, universal healthcare system since the early 1990s and co-sponsored the “Medicare for All” bill in 2017. She called bipartisan trade deals like NAFTA and the (now dead) Trans-Pacific Partnership “unfair.”

Her support of Wisconsin’s dairy and manufacturing industries may have won her unexpected allies — and foes. U.S. Rep. Glenn Grothman (R-Glenbeulah) says while meeting with Wisconsin foundry owners recently, he was dumbstruck to hear that Baldwin sided with them on a regulatory issue.

“I said something assuming that Tammy wouldn’t be on their side. But, ‘Oh no,’ they said. ‘Tammy did all we wanted. She’s a good friend of the foundries,’” says Grothman. “Would you have guessed that Tammy Baldwin would be a ‘good friend’ of the foundries? It surprised me.”

To the dismay of some environmentalists, Baldwin also joined climate change denier and Wisconsin’s senior Sen. Ron Johnson in cosponsoring a bill to delist gray wolves in the Great Lakes from the Endangered Species Act. Madison residents opposed to housing an F-35 fighter wing at Truax Field were angered that Baldwin lobbied hard to keep the war planes in town.

The senator also caught shade from vegan activists for proposing the Dairy Pride Act, which would prohibit almond, soy and other plant-based beverages from using the word “milk.” The animal rights group Direct Action Everywhere disrupted a 2017 Milwaukee town hall meeting hosted by Baldwin over her bill and support for the dairy industry in general. One protester questioned Baldwin’s lefty cred at the event.

“In keeping with the progressive values that you demonstrate in other areas, how about working instead for those who have no power in this issue?” the activist asked Baldwin. “A discriminated-against-group that is rarely talked about and heard from: the dairy cows in Wisconsin.”

Baldwin responded that visiting a dairy farm is an “awesome thing to do.”

“I am open to the perspective that you’re sharing,” she told them. “But right now, I have no apologies about the Dairy Pride Act.”

There are few alternatives to Baldwin for those that oppose her from the left, although Capitol protester Mary Jo Walters is running as an independent.

The real threat to Baldwin is out-of-state conservative advocacy groups, which started airing attack ads last year. According to Baldwin’s campaign, outside interest groups have already spent almost $15 million on this race.

“Huge expenditures on nasty attack ads by the Koch brothers network and Richard Uihlein,” says Baldwin. “It was stunning to see outside groups, that represent powerful interests, attack so early on.”

But Baldwin has a bigger war chest than both state Sen. Leah Vukmir (R-Brookfield) and political newcomer Kevin Nicholson. The latest campaign financial disclosures show Baldwin has raised more than four times the combined totals of her GOP opponents and spent accordingly. For the 2018 race, Baldwin has raised $21.5 million and spent $14.5 million; Vukmir and Nicholson have, collectively, raised $5.2 million and spent $3.6 million. As of June 30, Baldwin has $7.2 million cash on hand while her opponents have roughly $1.6 million combined in the bank.

× Expand Dylan Brogan Indivisible Door County volunteers are so inspired by her that they have planted handmade signs along state highways 42 and 57.

So far, Baldwin is holding her own in the polls. The July 27 poll conducted by NBC News/Marist College Poll has Baldwin 15 points ahead of Nicholson and 17 points ahead of Vukmir. The Marquette Law School poll from June 20 put Baldwin nine points in front of Vukmir and 11 points over Nicholson.

Black says those in Madison don’t realize the intensity of the attack ad campaign against Baldwin in other parts of the state.

“The Koch Brothers and the other right wing billionaires know it’s counterproductive to do an ad blitz in Madison right now,” says Black. “But in other media markets, Tammy is being absolutely slammed with the most vile kind of ads.”

Vukmir sent out a newsletter in May showing a picture of herself and CIA director Gina Haspel — whose nomination Baldwin voted against — with a “Team America” label. Baldwin is shown on the “Team Terrorist” side photoshopped next to Khalid Sheikh Mohammed, who helped orchestrate the Sept. 11 attacks.

The Stars and Stripes Forever PAC is running radio spots targeting African Americans claiming Baldwin “is a big reason why” one out of three aborted babies in America are black.

“That could be the next Frederick Douglass or Rosa Parks or Martin Luther King they’re aborting,” says a voice in the ad released in 2017. “How can Tammy Baldwin ask for our votes if she doesn’t even want our babies?”

That same PAC — which was formed to support Ben Carson’s 2016 presidential campaign — also released an ad in April accusing Baldwin of requiring American schoolchildren to learn things that are “often untrue,” including that Jews, Christians and Muslims all worship the same god. “Liberal Democrats like Tammy Baldwin support teaching about Islam,” says the narrator in the spot. “After all, if our kids think all religions are the same, they aren’t likely to choose any of them.”

Baldwin’s campaign has been more upbeat — even chipper. One spot opens with kids in a barn announcing “this is a going to a very cheesy ad.”

“When federal bureaucrats wanted to prohibit the use of wooden cheese boards — which help make tens of thousands of pounds of cheese a year — something had to be done,” Baldwin says in the ad. It then shows a cheesemaker saying Baldwin “stood up for businesses like ours.”

Another Baldwin ad features workers from Fairbanks Morse — a Beloit-based marine engine manufacturer — thanking the senator for her “Made in American Shipbuilding Act that makes sure ships built for our armed forces are made here in the U.S.”

What you aren’t hearing from Baldwin on the stump are many attacks against Trump or the Republican Party — at least by name. Wisconsin’s junior senator is more apt to say she’s standing up against “powerful special interests.” When she needs to fire up the base (and maybe court some independents), she turns to the yugest bomb-thrower on the left: 76-year-old U.S. Sen. Bernie Sanders from Vermont.

× Expand Baldwin turned to the left’s yugest bomb thrower, U.S. Sen. Bernie Sanders, to help fire up supporters in Eau Claire in July.

The ballroom at the Lismore Hotel in Eau Claire is filled to capacity on July 14. Baldwin is warmly greeted with applause and some “Tammy, Tammy” chants when she comes on stage.

“Washington is working for some. It’s working well for folks with powerful connections: the special interests. Time and time again, they call the shots to keep the system in their favor. And that’s what’s at stake this year,” Baldwin tells the crowd of about 1,000. “I’ll sit down with anyone — regardless of party — to get the job done.”

She ends her speech on a hopeful note: “They are pouring in more money against me than any other Democratic senator up for re-election this year. But I have something these special interests don’t.”

“Us!” shouts a woman in the crowd, right on cue.

While Baldwin is well received, Sanders blows the roof off the place. He is noticeably louder than Baldwin, both in volume and rhetoric. Baldwin’s criticism of opponents is focused on the issues. Sanders goes for the jugular.

“It’s such a disservice to our country that we have a president who is a pathological LIAR,” booms Sanders. “Trump says it was a ‘sign of strength’ to tear little babies away from the arms their mothers. I say to President Trump, that’s not an indication of strength. It’s an indication of moral weakness…. It’s not what this country is about and we will not let it — ever — be about.”

Some in the crowd, like Adolph King from the town of Seymour, are there mainly to see Bernie. King voted for Sanders in the primary, but then Trump in the general election. He’s unsure who he’ll support for senator. But his partner, Karen King, is on team Tammy. She’s worried about the renewed threat to legalized abortion with Justice Anthony Kennedy retiring from the U.S. Supreme Court.

“I’m old enough to remember when things were hard,” Karen says. “I don’t know how anyone could even think of negating Roe v. Wade.”

This is Selika Ducksworth-Lawton’s first political rally. The Baldwin campaign called and invited her to the event. “People in the north feel neglected,” she says. “We feel like nobody pays attention to us. We feel like the resources have been sucked out of us.”

Terry, who declined to give his last name, says he respects Baldwin’s civility.

“I was taught that you don’t lie. You don’t say bad words. You don’t talk bad about people,” says the Eau Claire man. “Tammy shows consistent good behavior. Hard to believe that’s an asset nowadays, but it is.”

Karin Johanson, who was Baldwin’s campaign manager in 2012, says that Republicans were warned by Paul Ryan — who was chummy with Baldwin since they frequently flew to Washington on the same flights — not to be fooled by Baldwin’s reputation for being a shy policy wonk. They didn’t listen.

“They don’t understand her appeal. She is very soft-spoken. She’s also very Wisconsin. So sometimes you don’t realize what a good politician she is,” says Johanson, who also worked on Wendy Davis’ unsuccessful campaign for Texas governor in 2014. “She’s very good at sticking to her message and she knows how to speak to all sorts of different people because at the end of the day, they are of Wisconsin and she is, too. People in Wisconsin are very proud of their state.”

Johanson says Baldwin is not a typical politician.

“Tammy is a very serious person. Is she as pithy as Elizabeth Warren? No. But is she as smart as Elizabeth Warren. Yes. You have no idea. She has the intellectual capability to be anything she wants to be. She’s a workhorse,” says Johanson.

“Kevin Nicholson says she’s an embarrassment. Leah Vukmir said a bunch of crazy stuff that’s totally untrue. Tammy would never say anything like that about anyone,” adds Johanson. “She goes about her business. She disagrees on policy and makes that clear. I think personality will stand her in good stead in this race.”

Right after the 2012 August primary, Baldwin launched a series of ads that highlighted Thompson’s career as a lobbyist after his tenure as governor. The catch lines on a few ads were “Tommy Thompson: he’s not for you, anymore.”

The ads came right after an exhausting primary that Thompson was not expecting and he was unable to counter Baldwin’s message. Johanson says the ads also rang true.

“After the primary, we went ahead in the polls. Much faster than we expected. But then we held it,” says Johanson. “They can try to make her into a caricature but it just doesn’t work. Her response is all the things she’s done for the state of Wisconsin. That’s what we did in 2012. I know that’s what she’s doing now.”

Marquette political science professor Julia Azari says a strong turnout of the base is essential for both major political parties in November. But winning over fickle voters may put Baldwin over the top.

“It does seem like there are these pockets in Wisconsin where people voted for Bernie in the presidential primary and then Trump in the general election,” says Azari. “That’s difficult for folks who live and breathe establishment politics to get their heads around. It’s hard to know how many of these people are actually out there. How many people voted for Obama and then Trump?”

Baldwin endorsed Clinton before Sanders had entered the presidential race. Mayor Paul Soglin, one of a handful of Wisconsin elected officials to back Bernie, says Baldwin is “probably closer to Sanders” than Clinton.

“A lot of people thought she was well-intentioned but not realistic when she launched her congressional career on making a national healthcare plan a reality,” says the mayor, who is also running for governor this year. “The Democrats have caught up to her on that. The extreme right-wingers will never forgive her.”

× Expand Republican Leah Vukmir (left) has falsely accused Baldwin of being in league with terrorists.

Baldwin doesn’t shy away from her progressive roots. But in 2018, the senator isn’t singing her liberal bona fides from the rooftop, either.

Meanwhile, both Vukmir and Nicholson aligned themselves with the president during a July 27 debate in Milwaukee. “I applaud President Donald Trump for saying, ‘You know what, I want to put America first. I don’t want people coming into this country if they are going to be a threat to our security and a threat to our Americans,’” said Vukmir, who has served in the Legislature since 2002. “He’s doing the right thing and I stand with him.”

But unlike Trump, neither candidate supports Baldwin’s Buy American provisions, which would require U.S. manufacturers to be used for some public projects.

Establishment Republicans are backing Vukmir over the newbie Nicholson, a Marine Corps veteran.

Johanson says it makes sense that in a GOP primary, Vukmir is running a “very, very conservative” race. But she’ll have to change her tune if she becomes the nominee.

“She will have to turn around and appeal to independent-leaning people. I’m not sure how she does that at this point. Baldwin has a lot of [independents] already. Leah Vukmir needs to peel them away,” says Johanson. “The Republicans have been going negative on Tammy Baldwin for a year. They don’t seem to be making much progress. Leah is going to have to say something new.”

Nicholson is more of a wildcard. Vukmir has been hammering him as a Johnny-come-lately since he used to be a Democrat. As reported by Daniel Bice of the Milwaukee Journal Sentinel, Nicholson’s parents are backing Baldwin over their flesh and blood — each have given the maximum donation of $2,700 the senator’s campaign. As a younger man, Nicholson was president of the College Democrats of America and spoke at the 2000 Democratic National Convention Convention. Today, he’s running as a Trump-styled outsider.

“We have to do things differently. You all knew this when you voted for Donald Trump,” Nicholson said at an April debate hosted by Americans for Prosperity. He blames “the establishment” for liberal-leaning justice Rebecca Dallet being elected to the Wisconsin Supreme Court.

“If we continue to replay these same mistakes — sending insiders to do a job that outsiders need to take care of — we’ll be sitting here talking about the exact same problems in six years,” he says.

Unlike in 2012, Baldwin won’t have President Obama at the top of the ticket. However, Azari says historically the opposition party fares well in the midterms.

“I think it’s a wash. Obama was helpful in 2012, no question. It also appears that this might be a good year for Democrats,” says Azari. “At least in Milwaukee and I suspect Madison, Democrats are fired up.”

Azari believes Baldwin can mend fences within the Democratic Party, too. Baldwin has a record that appeals to Midwest voters who may not have voted for Clinton in 2016 but she also speaks to “people that aren’t just straight white dudes,” Azari says. She describes Baldwin as an “established Democrat without necessarily being an establishment Democrat.”

Baldwin doesn’t deny that Wisconsin has become politically polarized. Even so, she believes she can continue to win over independents and even some Republicans by focusing on policy.

“The thing that defies polarization is people getting involved [in] issues…. I’m witnessing in 2018 one of those moments where people have really become engaged. And they’ve become engaged about issues,” says Baldwin. “[That] pivots to the election later. Then they want to do everything they can to support their champions and to get rid of the folks that have been obstacles of progress.”

Editor's note: This article originally stated that said Gov. Scott Walker is backing Vukmir in the GOP primary race. Walker's campaign says the governor is staying neutral in the race. However, Vukmir is supported by First Lady Tonette Walker and Walker's parents. And the governor's son, Alex Walker, is political director for Vukmir's campaign.