The Unnatural: How Mark Dayton Bested Scott Walker—and Became the Most Successful Governor in the Country

For a man who has won a competitive US Senate race and secured his second term as governor in November, Mark Dayton is a terrible retail politician. "He's very shy and he's an introvert," Ken Martin, the chair of the state party and a friend of Dayton's, told me unprompted earlier this month. "He's not a typical, backslapping politician," Martin continued. "He's not very articulate; he's kind of jerky," Tom Bakk, the Democratic Senate majority leader, says of his ally's style. When Dayton first ran for his current job, in 2010, The New Republic dubbed him "Eeyore for Governor."

An heir to the Target retail fortune, Dayton, 68, has plowed tens of millions of his own money into his campaigns, but it still hasn't come easy. He swallows his words in a rush, speaking in almost-unintelligible mumbles and frequently losing track of his point as he rambles on unrelated tangents. "He's not a terribly articulate guy," says Larry Jacobs, chair of the University of Minnesota's public policy school. "He's not a smooth talker; he struggles to give a smooth public speech." At public events, Dayton hunches his shoulders, which makes him appear shorter than his 5-foot-10 frame, and often appears to be trying to disappear into the crowd. No one wonders whether he'll seek national office someday. He's not the leader of the free world—he's your dad, struggling to make small talk with you and your friends after you get home from school.

Eeyore did well for himself. Photo: Glen Stubbe/ZUMA; photo illustration by Carolyn Perot

Think of Dayton as Scott Walker's mirror image. With the help of GOP-controlled legislatures, Walker and other Republican governors, such as Kansas' Sam Brownback, have passed wish lists of conservative policies and touted their states as laboratories that demonstrate the benefits of conservative governance. Walker, the governor of Wisconsin, has parlayed that hype into a potential 2016 presidential run. And across the border in Minnesota, Dayton seized a brief moment of unified Democratic control to create the liberal alternative to Walker's Wisconsin—a blue-state laboratory for demonstrating the potential of liberal policies. Dayton didn't "set out" with the objective of one-upping Walker in mind, he told me after the Eagan event. But "the contrast," he notes, is obvious.

Over the past several years, Minnesota has become a testing ground for a litany of policies Democrats hope to enact nationally: legalizing same-sex marriage, making it easier to vote, boosting primary education spending, instituting all-day kindergarten, expanding unionization, freezing college tuition, increasing the minimum wage, and passing new laws requiring equal pay for women. To pay for it all, Dayton pushed a sharp increase on taxes for the top 2 percent—one of the largest hikes in state history. Republicans went berserk, warning that businesses would flee the state and take jobs with them.

The disaster Dayton's GOP rivals predicted never happened. Two years after the tax hike, Minnesota's economy is booming. The state added 172,000 jobs during Dayton's first four years in office. Its 3.6 percent unemployment rate is among the lowest in the country (Wisconsin's is 5.2 percent), and the Twin Cities have the lowest unemployment rate of any major metropolitan area. Under Dayton, Minnesota has consistently been in the top tier of states for GDP growth. Median incomes are $8,000 higher than the national average. In 2014, Minnesota led the nation in economic confidence, according to Gallup.

Minnesota has even pulled ahead of Walker's Wisconsin, leapfrogging its neighbor to the east on measure after measure. "In a whole number of ways, we're very, very similar," Bakk, the DFL Senate leader, says of the two states. "But politically, we have taken just totally different paths in the road."

Dayton cruised to a 5-point win in 2014, spending just $3 million in a race that received scant national attention. All Minnesota's governor had to do was point to his policy successes. "We've confounded those who said if you're going to raise taxes on the richest people they're all going to leave the state, and all the businesses are going to leave the state and we'll have this enormous drain on jobs. That hasn't happened," Dayton told me in October.

"I feel affirmed in my political views," he says now, "and that the direction we've taken in Minnesota is much better for our state and for most of the people in Minnesota than what's happened in Wisconsin. The numbers show that unmistakably…I still think they're the right politics for the Democratic Party—and the right policies for our country."

Before his time as governor, Dayton was largely seen as a lovable but aimless rich boy who had tried and failed to succeed in politics. In his 30s and 40s, Dayton spent millions of dollars of his own money losing two statewide campaigns—a Senate race and a gubernatorial primary. When he finally won a Senate seat, in 2000, he served a spectacularly unsuccessful single term before declining to run for reelection. "He's a nice guy, but he's a trustafarian," says Stan Hubbard, a billionaire media mogul and prominent funder of GOP causes in Minnesota.

Dayton's money comes from his family. His great-grandfather George Dayton founded a department store named after the family in 1902. George Dayton's heirs built the nation's first fully enclosed mall in Edina in 1956. In 1962, the family branched out, opening the first Target in Roseville, Minnesota. A Dayton's department store anchored most Minnesota malls until 2000, when the Dayton-Hudson Corporation became Target Corporation.

The Target wealth—the family fortune is estimated at $1.4 billion—bankrolled Dayton's runs for office. But that privileged upbringing also turned the millionaire heir into a devoted liberal—the sort of second-generation plutocrat who knows the inequality of the system firsthand and wants to tear it down. "To whom so much has been given, to him so much be required," Dayton recalls as his father's favorite Bible saying, and at first Dayton studied to be a doctor before engaging with '60s politics in college. Dayton became a campus radical during college at Yale, and protested Honeywell's role in making bombs for use in Vietnam even as his father sat on the company's board. After he graduated in 1969, Dayton taught at a school on the Lower East Side of Manhattan and then transitioned to social work at Project Place, a South Boston-based organization that works with homeless young people. Dayton's annual $30,000 donations covered a tenth of his employer's budget. After four years in Boston, Dayton turned to politics, breaking from his Republican parents to fight for liberal causes. He worked as an aide in Minnesota Sen. Walter Mondale's office, then moved to Atlanta to work on Mondale's vice presidential campaign. He was an original donor to Mother Jones in the 1970s. He even managed to earn a spot as the lone Minnesotan on Nixon's so-called "enemies list"—a fact he would cite during his early political campaigns.

In 1982, when he was 35, Dayton ran for Hubert Humphrey's old Senate seat, then held by Republican David Durenberger. Dayton called his wealth his "original sin" and promised to close tax loopholes for corporations and the rich alike. The family business was the seventh-largest nonfood retailer in the country at that time, and Dayton sold off a large chunk of his shares to eventually throw $7 million of his own money into the campaign, which became one of the most expensive Senate races ever. But Durenberger tied his fortunes to the popular Ronald Reagan, attacked Dayton as a political novice unprepared for the job, and easily held on to his job.

After the loss, Dayton struggled with alcoholism, but got sober—he checked into the Betty Ford clinic in 1987—and reined in his ambitions. In 1991, he ran a successful campaign for state auditor, serving an unremarkable four-year term. In 1998, he lost a gubernatorial primary to Humphrey's son Skip, but he ran for statewide office again in 2000, forgoing "an expedition to the North Pole to make his second Senate run," according to the Philadelphia Inquirer. Dayton spent $12 million of his own money and was able to oust the incumbent, Republican Rod Grams.

But Dayton picked a terrible time to join the Senate Democratic caucus. He spent just 18 months in the majority when he was still a junior senator with little sway. With Democrats otherwise in the minority, he couldn't pass anything of consequence and grew visibly bored with the job. "The reality, he quickly learned, is that being 100th out of 100th in terms of seniority in the US Senate is not a good place to be," state party chair Martin says. "It was just a lot harder for him to do the types of things he wanted to do." At first, Dayton had Paul Wellstone, a fellow liberal Minnesotan, to offer guidance and keep him company in Washington. That changed after Wellstone died in a plane crash 11 days before the 2002 election. "It really soured him on Washington and changed his perspective quite a bit," Martin says. "It became a lot more miserable for him being out there without Paul."

Dayton became one of just 23 senators to vote against the Iraq War, but his liberalism made it next to impossible to get anything done in the GOP-controlled Senate. Uninterested in the drudgery of legislative bickering, he came unmoored. He would later admit that he struggled with alcoholism and depression during the end of his tenure into the Senate.

In 2006, Time declared Dayton one of the five worst senators in the country, and even he couldn’t really disagree, grading his term in office an F for job performance (he did, however, give himself an A for effort). "I found my role in the Senate extremely limited…Effectiveness in the Senate is majority and seniority, and I had had neither," Dayton told me over the phone last week.

He skipped running for reelection to spare himself the hassle of fundraising (he didn't want to be the only person funding his campaign) and the embarrassment of a likely loss. "There will be plenty of Democrats who will say he had his chance, and he blew it," political scientist Steven Smith decreed when Dayton left office in 2007. "They will make a credible argument that he will not make a great candidate. He came across in the eyes of many Minnesotans as a lightweight as US senator."