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Commentary

October Surprises

A green school bus, a letter that backfired and a memorial that did too. Minnesota knows a thing or two about October surprises.

6:09 PM CST on November 7, 2026

(Image: Paul Wellstone campaign)

(Image: Paul Wellstone campaign)

By the time you receive this issue of the Hill & Lake Press, the midterm elections will be over and, barring a lengthy recount (or “outside interference”), we will have a new governor, a new senator and a new county attorney.

But I’m writing this nearly three weeks out, and an October surprise could still happen, as it did in Paul Wellstone’s first campaign for the Senate in 1990.

Out of Northfield

Wellstone came out of nowhere. OK, out of Northfield, where he was a tenured professor of political science at Carleton College. If he was known at all, it was as an organizer and activist, a leader in what Rep. John Lewis would later call “good trouble.” His only political experience was running for state auditor a few years earlier and losing to Republican Arne Carlson.

“ It turned out that voters didn’t care about what kind of Jew he was. They cared what kind of senator he would be.”

Political bigwigs argued that Wellstone was too unknown and too radical to win. Only his wild-haired, bright-eyed students and a few farsighted urban progressives, including Sam and Sylvia Kaplan, were backing him. But with the power of his ebullient personality and the passion of his supporters, he won the DFL endorsement over a well-known and respected state legislator, Tom Berg (a Hill & Lake neighbor at the time).

His opponent was incumbent Rudy Boschwitz, the owner of Plywood Minnesota, who appeared in TV ads wearing a plaid shirt and being an affable Minnesotan. (Both men came from Jewish immigrant families: Boschwitz’s fled Nazi Germany when he was a small child, and Wellstone’s parents came from Ukraine.)

Boschwitz outspent Wellstone 7-to-1, but Wellstone out-campaigned Boschwitz 50-to-1. His ads were quirky and fun to watch. He traveled the state in a battered green school bus. His old-fashioned stem-winder speeches roused people to their feet, especially young people who had never heard anyone like him. And he organized, organized, organized, as he always urged us to do.

The First Surprise

He closed the gap. Boschwitz held the lead, but as the election grew near there was talk of an upset. And then we got an October surprise.

Just days before the election, a group of Boschwitz’s supporters sent a letter to members of the Jewish community urging support for Boschwitz. In what became known as the “good Jew” letter, they wrote that Wellstone, although Jewish by birth, was not a good Jew like Boschwitz. And he had married a woman who was not Jewish.

Boschwitz distanced himself from the letter, but it hit his campaign like a torpedo. Wellstone went on to win with 50.49% of the vote.

It turned out that voters didn’t care about what kind of Jew he was. They cared what kind of senator he would be. He didn’t tell them who he was; he wanted to know who they were. His identity was secondary to his ideals. His wardrobe secondary to his words.

A Tragic Surprise

In 1996, he once again defeated Boschwitz. In 2002, he was in a close race against former St. Paul Mayor Norm Coleman when he, along with his wife, Sheila, daughter Marcia and several staff members, was killed in a plane crash in the brushy woods outside Eveleth on Oct. 25. It was a tragic October surprise that no one should ever experience.

Former Vice President Walter Mondale stepped up to run in his place, and a new campaign had to be assembled in just days. With his name recognition and sympathy for the Wellstone family’s loss, Mondale seemed on track to win.

But a hastily put-together memorial service at Williams Arena delivered another October surprise. The memorial went off script into what some described as a political rally. Vin Weber, a Republican operative at the time, later described seeing that memorial and having a light bulb moment: Instead of building sympathy for the Mondale campaign, the service could be turned against him. And it was. Norm Coleman became our senator.

“ His identity was secondary to his ideals. His wardrobe secondary to his words.”

A Surprise for Governor

Curiously, in 1990 Arne Carlson became a last-minute candidate for governor, also because of an October surprise. Jon Grunseth, the Republican nominee, was forced to drop out nine days before the election over allegations of sexual impropriety.

Carlson, then the state auditor, stepped in and went on to defeat incumbent Gov. Rudy Perpich.

What We Will Know

These October surprises happened before early voting was an option in Minnesota. Would they have the same impact on results today? We’ll never know.

But we will know whether a candidate can still out-organize and prevail, with or without a surprise, as Wellstone did in 1990.

Susan Lenfestey writes for the Hill & Lake Press. She lives in Lowry Hill.

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