Can Cort VanOstran Beat Ann Wagner on her Own Turf?

On a Sunday morning in late September, Cort VanOstran steps outside to the parking lot behind his two-bedroom apartment in Clayton.

It is about 7:20 a.m., shortly after sunrise. Cars shooting past on South Hanley Road still have their lights on. Campaign staffer Alex Dubinsky is already waiting beside an idling Honda Fit. He stashes a few "Cort VanOstran For Congress" yard signs behind the back seat and says he has the stereo cued up with some classic rock to get them going. VanOstran laughs.

"Alex is nineteen, so what he considers 'classic' can be kind of offensive," he explains.

Not that VanOstran grew up in the era of hairbands, either. The lawyer with blond hair and a boyish face is just 30 years old. Dressed casually in a T-shirt, gym shorts and running shoes, he could be a grad student getting an (extra) early start on kegs and eggs. But today, like every day since VanOstran launched his campaign fourteen months ago, is a workday. Over the next eleven hours, he will hit four events scattered across Missouri's Second Congressional District and fill the time in between calling as many potential donors as possible.

It is a grueling schedule, to be sure, but one that seems to be paying off. He won a hard-fought primary in August, capturing more than 40 percent of the vote despite a field of four competitors. Political analysts now put the Joplin-raised Harvard grad within striking distance of U.S. Representative Ann Wagner (R-Ballwin), a three-term incumbent who has dominated a succession of Democrats going back to 2012.

On the drive to the 5K, VanOstran and Dubinsky are in good spirits. Dubinsky jokes that he is racing to win, while VanOstran promises to jog instead at a "politician's pace" — slow enough to smile and wave.

In the parking lot, they meet up with VanOstran's campaign manager, Claire Botnick, and 23-year-old sister, Callie VanOstran. After a quick greeting, they split up, each meshing easily into small clusters of the fit and politically active. The race is sponsored by Clean Missouri as part of its campaign for election and lobbying reforms, and so the crowd is packed with politicos.

This morning is less about campaigning per se and more about checking in with supporters before the final weeks' sprint. VanOstran glides from conversation to conversation, handshake to handshake. "He's a mingler," Dubinsky says.

One of Clean Missouri's goals is to revamp the process for drawing election districts. To illustrate the point, the route is a nonsensical series of twists, doubling back on itself and changing directions, gerrymandering in road-race form. As runners gather at the start line, the emcees call a young woman to the front and joke that in the spirit of Missouri elections they have declared her the winner before the race has even begun.

VanOstran, a regular runner, gamely jogs alongside a friend and Dubinsky for two miles before Dubinsky dashes ahead — earning him office bragging rights. VanOstran finishes in a respectable 25:59 and is quickly back to working the crowd, sweating but smiling.

Clean Missouri campaign director Sean Soendker Nicholson, no stranger to Missouri politics, predicts this could be a year of shakeups. "He picked a good year to run," he says of VanOstran.

The young lawyer makes it look easy, effortlessly chatting up strangers and allies, teasing Dubinsky about abandoning his running buddies. The people who've known him the longest say he's always been good at this. He makes friends and moves forward, always excelling, always reaching out. He learned long ago how to thrive during the struggle.

In August 1997, less than three weeks before Cort VanOstran's ninth birthday, his father killed himself.

Charles "Andy" VanOstran, a flight medic, had moved his young family from Joplin to Columbia, Missouri, the year before. He planned to go to medical school. Instead, he committed suicide at age 28, leaving a widow and three children. Cort was the oldest child.

His grandmother, Barbara Riechman, remembers that birthday. "We did everything we could to make the best of it," she says.

In a bolt of inspiration, Riechman, now 74, came up with a detective contest for young Cort's party. The rules are vague in her memory, but she remembers that kids and adults played together.

"There was an hour there I could see all of those kids having fun," she says. "I can tell you it was the best feeling."

When VanOstran mentions his father's death, it is usually an introduction to his mother. He typically explains that after his dad died, Cathy VanOstran devoted her life to her children. As a single mom, she raised two boys who would go from rural Missouri to Harvard and a daughter who has done humanitarian work across the world. Riechman says her daughter, a teacher, stayed single after her husband's death in order to focus on the kids.

Cathy VanOstran died in 2016, two years after she was diagnosed with breast cancer. VanOstran cites her death as the impetus for his congressional bid, pointing out in campaign ads that Wagner gleefully voted to eviscerate the Affordable Care Act, which his mother relied on during her last years.

Even when he was young, VanOstran was included in important family decisions. He was suddenly the eldest male, and relatives say he grew up faster than most kids.

"I know in those weeks after, Cort at eight years old had a sense that he needed to help out more than most eight-year-olds," sister Callie VanOstran says. "I think it shaped both of us in who we are today. Caring for others is something we want to do with our lives."

VanOstran has posted the number to the National Suicide Prevention Lifeline on social media and called for more discussions of mental health. But his father's death is not something he publicly dwells on. Often, when speaking to groups, he says he "lost" his father at a young age or his dad "passed away" before moving on to his mother.

In an interview, he says he was "very aware" as a kid of the suicide.

"I mean, I was there when he..." VanOstran says before redirecting. "I have very vivid memories of that day."

He looks back on that time with new understanding. "I think about, now I am about the age my mom was when my dad passed away," he says. "So it's only really now that I realize what an absolute tragedy that must have been for my mom and what a sort of life-altering thing that must have been to have three kids under the age of ten and to have your partner, you know, take his life like that. I can't imagine what she went through."

The family moved back to Joplin a year after the suicide. Callie VanOstran says their mom ensured theirs was a happy home.

"My mom was very intelligent, very witty in fact," she says. "She always had a comeback. She was the relaxed one. She made sure we were all enjoying life."

After his dad's death, VanOstran read hungrily, tearing through Roald Dahl, the Boxcar Children, Goosebumps and Beverly Cleary series. He says that turned into a love of school and learning.

"I think in any tragedy, you can find a silver lining, and I think you have to look at the good things that can come out of something bad," he says. "That was a good lesson, frankly, to learn early."

Retired Joplin High School teacher Leann Stausing first met VanOstran in one of her English classes. He seemed more grown-up than the other kids.

"He is absolutely one of my most memorable students," she says. "He has a brilliant mind. He is a hard worker, and he is so goal-oriented."

He did a little of everything in high school. Profiles in the Joplin Globe list activities and awards including National Merit Scholar, show choir, Key Club, Fellowship of Christian Athletes and National Honor Society. He was the prom king, student council president and the male lead in two plays, portraying the wealthy Horace Vandergelder in Hello Dolly and the handsome Jimmy Smith in Thoroughly Modern Millie.

A teenage VanOstran told the Globe he planned to study law and hoped to be a U.S. senator one day. Such ambition isn't always easy to live with; he was such an orderly kid that he recalls taping a divider across the bedroom he shared with his younger brother Collin, hoping to protect his side from his sibling's messier habits.

Stausing says she knew early on that VanOstran wanted to go to Harvard and helped advise him on his application essays. Not many Joplin kids leap to Cambridge, but Stausing says his discipline and work ethic made it seem inevitable.

"I was glad when he got his acceptance and it was in hand, but I really never had much doubt he was going to get in," she says. "And I don't think anybody in the school was shocked."

Stausing retired in 2008 after 45 years and relocated to northwest Arkansas. She eagerly follows her star student's campaign.

"I'd sure come up and vote for him if I still lived in Missouri," she says.

Little more than two hours after running 3.1 miles in Clayton, VanOstran takes a seat in his campaign office in Webster Groves and settles in for every candidate's most-hated task — dialing for dollars.

He has traded his gym clothes for the outfit of the casual attorney: Polo-brand blue-checked shirt, slim-fit Levi's and dark leather boots. His blue blazer is draped nearby.

He has a lot of work to do to beat Ann Wagner. The 56-year-old Republican has had a stranglehold on the district since winning her first House race in 2012, and she's been a major player in the state party since at least the 1990s.

The daughter-in-law of the late anti-abortion activist Loretto Wagner, she rose from local committeewoman to chair the Missouri GOP and co-chair the Republican National Committee. In 2005, then-President George W. Bush appointed her ambassador to Luxembourg, a post she held for four years.

Historically, the Second District has been a perfect fit. Redrawn after the 2010 Census in a power play that wiped out Democrat Russ Carnahan's district, it is majority Republican. It is nearly 90 percent white with good schools and covers the affluent suburbs to the west of the city, angling south into Jefferson County.

It also includes the Clayton headquarters of rental-car giant Enterprise, where her husband's ties as a company executive and lobbyist have been a fundraising windfall.

"We have a going on two-decades relationship with Enterprise," the congresswoman told the St. Louis Post-Dispatch in 2012, when the paper reported major donations from company employees and their relatives. "It's a family."

Wagner has continued to excel at raising money. She took in more than $2 million in 2017, and she had nearly $3 million in cash on hand by mid-July of this year.

Normally, it easily would be enough for Wagner to bury any challenger. But political analysts suspect this year could be different. Nationwide, there are signs that voters, particularly female voters, in suburban districts such as Missouri's Second have had enough of a smack-talking president who continues to side with the NRA after school shootings, has no discernible plan for an Obamacare replacement and mocks the #MeToo movement.

Shifting attitudes have put once-reliably Republican strongholds in play, analysts say. "As we've seen across the country, suburban House districts have really swung to Democrats," says Dave Robertson, a political scientist and professor at University of Missouri-St. Louis. The Pennsylvania Rust Belt district where Democrat Conor Lamb narrowly won a special-election victory in early March was considered more Republican and more pro-Trump than Missouri's Second, he notes. Trump's margin of victory there was twenty points, compared to a little better than ten on Wagner's turf. The more moderate Mitt Romney did better in 2012.

The nonpartisan Cook Political Report shifted its view of the district from a "likely Republican" to "lean Republican" in September. The national Democratic Congressional Campaign Committee has also noticed, adding VanOstran to its Red to Blue program, designed to flip vulnerable Republican districts.

Wagner, who has made opposition to sex trafficking a major focus, denounced Trump during the 2016 campaign after his "grab them by the pussy" comments but has since embraced his presidency, voting with his positions 97 percent of the time, according to analysis by FiveThirtyEight. She continues to push stalwart Republican issues: anti-abortion legislation, support for the military and increased security. (Wagner did not respond to interview requests.)

VanOstran counters with support for health-care issues, such strengthening the Affordable Care Act. He also notes Wagner's vote against the Violence Against Women Act, which designates resources to help battered women. He favors stronger gun regulation and a woman's right to choose. So far, endorsements include United Steelworkers, Planned Parenthood Action Fund and Everytown for Gun Safety.

Kelli Dunaway, an early challenger in the Democratic primary, was initially skeptical of VanOstran. "I was like, 'Goody, just what we need, more straight white guys,'" she says. But she dropped out of the race before the primary and endorsed VanOstran. "I know Ann Wagner is a woman, but she is such a privileged woman," she says. "She has such a limited view."

Still, Wagner is a three-term incumbent and a Republican-party power broker for decades.

"She is not just supported by the Republican establishment — she is the Republican establishment," Robertson says, adding, "The fact that she is vulnerable speaks volumes about the Republican party."

Vulnerable, VanOstran knows, is a long way from defeated. He needs more name recognition, more TV ads, more money. Adding a degree of difficulty, he has refused corporate cash. It is a position that distinguishes him from Wagner, who by mid-July had accepted nearly $1.3 million from political action committees. It also plays well with voters, but the high ground does not get your ads on TV.

And so, for 30 hours every week, VanOstran is on the phone, calling potential donors. In his Webster Groves office, he sits at a table with campaign finance director Clark Conlisk and deputy finance director Samuel Rebmann.

By now, they have a routine. VanOstran and Conlisk both dial from a long list of potential donors. Most calls go to voicemail. But if Conlisk gets a live person on the phone it sets off a merry-go-round of action. After a quick greeting, he hands his cell over to VanOstran, who makes the pitch directly even as he passes his phone to Rebmann. Again, most calls go to voicemail, so Rebmann will likely leave a message. If someone picks up, he hustles out of the room, so he and VanOstran and possibly Conlisk are not all talking over each other. When the calls eventually clear, they begin again.

The intricate choreography can be a bit confusing to watch, but the three seem at ease, chatting about fantasy football or campaign strategy during the occasional dead spaces. VanOstran picks up a basketball from the worn carpet and tosses it in his palm as he wanders around the room.

As much as anything, it is his ability as a fundraiser that first marked VanOstran as a serious contender. He had $454,219 on hand by the July reporting deadline — not Wagner money, but groundbreaking for a Democrat in that district, and enough to get on TV. By the end of September, he will have completed his best quarter yet, raising just shy of $750,000.

On this Sunday, he plows through nearly two hours of rapid-fire calls, and then heads out the door to his next event. As he rides along, Conlisk texts him more names and numbers. He gets to dialing.

VanOstran seems happiest bouncing from event to event. He describes the endless calls to beg donors for money as "energy-taking." Canvassing, knocking on doors is "energy-giving," he says.

On this Sunday afternoon, he cheerfully rides shotgun in a Subaru Forester, while his campaign manager, Claire Botnick, preps him for the rest of the day. Botnick's husband, Aaron Davidowitz, is in town for the weekend from New York City and is acting as chauffeur. The three were classmates, and close friends, at Washington University Law School.

After graduation, Botnick and Davidowitz moved to New York, where he became an assistant district attorney in Manhattan and she landed a position as an associate at Cravath, Swaine and Moore, one of the nation's premier law firms.

Botnick had never managed a campaign before, but when VanOstran decided to run, she agreed to take a sabbatical and return home to St. Louis. The work suits her. Just as much of a grinder as VanOstran, the 32-year-old has proven to be sharp tactician. Political watchers describe her as brilliant and credit her as the campaign's secret weapon.

"I don't think it's a secret," says Mark Osmack, who would know — he finished second to VanOstran in the Democratic primary.

As the trio cruises toward the first of three afternoon events, Botnick goes over the schedule and tries in vain to get VanOstran to eat lunch or at least a snack. They arrive at 1 p.m. at the Kirkwood home of Democratic boosters John Bedwinek, a prominent oncologist, and his wife, Anne, a speech pathologist.

They're mindful of their 2 p.m. town hall in St. Peters. "Everyone hold each other accountable for leaving at 1:20," Botnick says as they get out of the car.

The Bedwineks have a gorgeous place, set at the end of a long, curved drive. Anne Bedwinek greets them warmly and ushers them into a front parlor for a photo. "What time do you want me to introduce you?" she asks.

"Whatever time works for you," VanOstran says. "I think we just have to leave about 25 after."

Like most fundraisers on this day, a constellation of candidates are on hand. The headliner is state Auditor Nicole Galloway, who has a key position this cycle as the lone Democrat holding statewide office. Normally, she would speak first, but knowing VanOstran is on a tight schedule, she graciously allows him the opening spot.

He gives a version of his spiel in front of the Bedwineks' fireplace, explaining to a crowd of nearly two dozen the reasons he decided to run and the difficulty he faces against an establishment incumbent. He comes off as genuine in person, but he's not above a politician's pun.

"We are in the Show-Me State," he says. "I wish someone could show me where Ann Wagner is because she doesn't show up for us."

He speaks for about five minutes before handing off to Galloway. And then they are back out to the Subaru, minus Davidowitz. Gregarious to a fault, he somehow struck up a conversation on his way out. Botnick looks down the drive with lighthearted exasperation.

"The man literally cannot make an exit," she says.

Moments later, Davidowitz comes sprinting up the drive, saying something about meeting a friend of a friend, which required a selfie. VanOstran laughs, and all three are grinning as they get back in the car at 1:26 p.m.

On the ride to St. Peters, they return to campaign mode. Botnick quizzes VanOstran on potential questions he might face at the town hall: health care, the environment, support for police, NFL players kneeling for the anthem. They are constantly honing their message, sharpening their arguments. VanOstran seems to enjoy this, too — the National Merit Scholar happily churning through his homework.

They cross the Missouri River into St. Charles County and make their way to an outpost of Llywelyn's Pub. About 40 minutes after leaving Kirkwood, they pull into the parking lot. As they walk toward the door, a young man brandishing a smartphone tries to buttonhole VanOstran.

"Cort, one question: Do you plan to repeal the tax cut?" he demands.

Publicly, Wagner has ignored VanOstran. Following the strategy of many an incumbent, she never mentions his name in ads or engages.

"I think she thinks she's got this, which is a gross misunderstanding," Osmack says. "Cort's got a lot of support, a lot of backing."

The apparent theory is that engaging would only amplify VanOstran's name recognition — and could only hurt her. Without much direct confrontation, the campaign remains relatively clean. Compared to the slugfest between U.S. Senator Claire McCaskill (D-Missouri) and her Republican rival, Attorney General Josh Hawley, the race for the House is decidedly civil.

However, the young man at the door signals that Republicans take VanOstran seriously. He's a tracker, tasked with appearing at campaign events and recording in hopes VanOstran says something regrettable.

"Hi, Freddy," VanOstran says with a quick smile before breezing past. He has described GOP tracker tactics as cynical, but later he will use the episode to needle Wagner.

"In the spirit of full transparency," he says, "it's pretty likely that we would send someone to her events, too — except she doesn't hold public events."

The only town halls Wagner has held during any of her three terms have been by phone or at private companies, designed for their employees, according to Politifact. In response, VanOstran has made public events a key part of his campaign, appearing in libraries, meeting halls and the occasional bar all across the district.

In Llywelyn's, a side room is already packed with about 50 people, more than a third of them in T-shirts for Moms Demand Action, an organization working for tougher gun laws. Campaign volunteers hustle to set up a sound system and pass out cards for people to write down questions.

VanOstran opens with his critique of Wagner as an absentee politician. "I promise I will continue to hold town halls regularly," he says. "I cannot promise there will always be beer."

Unsurprisingly, the first question from the audience is about preventing gun violence.

"Let's be clear, the gun-violence epidemic in this community does not have to be this way," VanOstran says, before diving into his upbringing around the gun culture of southwest Missouri. He adds that he respects the protections of the Second Amendment. "But I also know that 80 to 90 percent of Americans agree that there is a lot more that we can do to keep our kids safe from the plague of gun violence."

He offers support for universal background checks, closing the gun-show loophole, limiting magazine capacities and legislation to keep domestic abusers and people on terrorism watch lists from owning guns. During the next 40 minutes, he will answer questions on the Environmental Protection Agency, partisan politics, teacher salaries, Obamacare, repairing roads, the opioid epidemic and even the Electoral College. He is asked his top three issues, which he lists as health care, gun violence and campaign-finance reform.

Ken and Sara Snyder of St. Peters listen while minding their young daughter. "I wasn't surprised by anything I heard," Ken Snyder says, "but I was definitely impressed." He compares VanOstran to Beto O'Rourke, the progressive Texas congressman whose campaign to unseat U.S. Senator Ted Cruz (R-Texas) has made him an online star.

Sara Snyder says VanOstran's passion about health care struck her as genuine.

"I think there's something really important about connecting on an issue at a personal level," she says.

After a quick lunch with campaign staffers at Llywelyn's, VanOstran has a decision to make.

He had penciled in a 4 p.m. fundraiser for Jean Pretto, an Oakville Democrat running for an open seat in the Missouri House. It was a late addition, and VanOstran had planned to meet his sister for the 5 p.m. service at the Gathering United Methodist Church. Pretto's home is 40 minutes away in south St. Louis County. Dubinsky informs VanOstran they are already late, and if they go, there is no way church with Callie is happening.

VanOstran thinks it over for a few moments. It is not even clear whether they have promised Pretto they would attend.

"Maybe we should go, either way," he says. He calls Callie to let her know, and Dubinsky steers them south toward I-270. You don't make it to Harvard from small-town Missouri — much less to Congress — by quitting work early.

Pretto is happy to see them when they arrive. The daughter of a Teamster who worked for Anheuser-Busch, she taught music in south-county schools. About a dozen people are gathered. Her husband Joe, also a Teamster who retired from Vess Soda, mans a tent with Budweiser, liquor and a spread of food that includes his own spicy sausages, which he urges VanOstran to try.

While Pretto works the crowd, Joe introduces VanOstran to his brother, Richard. The two of them are Vietnam vets. They grouse about former Governor Eric Greitens.

"I hated that guy," Richard says.

VanOstran replies, "He clearly wasn't in it for the right reasons."

When he is called to speak, VanOstran gives a shortened version of his standard talking points. He is here more to support Pretto than campaign for himself.

"She's going to be a phenomenal rep in Jefferson City," he tells the group.

He and Dubinsky hang out for the other speeches. He has a few pieces of spicy sausage, which he says are pretty tasty. After about 30 minutes, he and Dubinsky say their goodbyes and walk back through the neighborhood to the hatchback.

"That was a great day for me," he says, enjoying his time away from the phone. "That was the lowest ratio of call time in a long time."

Dubinsky selects some Beatles and steers the Honda back onto the road. The song is "The Battle of John and Yoko": You know they didn't even give us a chance. Christ, you know it ain't easy. You know how hard it can be. At the end of a long day, it feels spot-on.

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