Some of my biggest mistakes – and lessons learned – in politics

As my friend and former Missouri Democratic Party Chairman Stephen Webber likes to say of politicians, it’s hard to be great until you lose.

Bill Clinton’s 1974 loss to Congressman John Paul Hammerschmidt brought exposure to conservative voters in what was then Arkansas’ most Republican quadrant, helping Clinton hone a centrist message that got him elected statewide five times and win the White House in 1992.

George W. Bush narrowly lost a 1978 congressional race after his opponent, Kent Hance, castigated Bush for running an ad advertising a university campus campaign rally that Hance deemed an effort to “persuade young college students to support him by offering them free alcohol.”

Bush learned a life lesson about the political power of Christian conservatives.

Barack Obama got his head handed to him by Congressman Bobby Rush in a 2000 House primary. Rush framed the race as “the (Black) Panther against the professor,” dubbing Obama an “educated fool” who “read about the civil-rights protests and thinks he knows all about it.”

Obama learned that he could have more policy chops than Washington’s wonkiest think-tankers, but voters wouldn’t care if they didn’t trust the messenger.

Needless to say, my political career didn’t go nearly as far as theirs. But I did make more than my own share of mistakes and learned lasting lessons — some of which may be useful for 2022 candidates.

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Let’s start when I was raising money for my first race, a 2004 congressional primary against Missouri political scion Russ Carnahan.

Early in the campaign, I had lunch with a wealthy businessman who regularly wrote $25,000-$100,000 checks to the Democratic Party. He was the largest donor, and probably the wealthiest person, I’d ever met. 

We had a lively conversation, finding lots of common ground, and he said he’d gladly contribute to my campaign. I figured that given his wealth and past contributions, he would certainly max out, since the federal limit that cycle was just $2,000. My plan was to get the $2,000, then call in a few months to solicit $2,000 from his wife, and just maybe, if we kept building a relationship, see if his adult kids might donate.

So, I slid him a remit envelope, thanked him in advance for his generosity, and strolled out of the restaurant on cloud nine — my first mega-donor!

A week later we received his check…for $200. A total kiss-off.  

I called him every two weeks for the next 9 months and never heard back from him.

Lesson: Always ask for a specific amount.

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A second mistake I made during that race involved a 77-mile journey from the northern edge of my district to the site of a proposed cement plant near the southern tip. I was trying to burnish my environmental bona fides both by riding my bike cross-district and protesting a plant which the Sierra Club projected to be a significant polluter. 

I also needed a fresh fundraising strategy, like asking people to pledge a few bucks a mile instead of calling with yet another stale $250 ask.

So I rode. And rode. Started with 30 volunteers alongside me. Ended with just me and one staffer. 

When we pulled up to the construction site, there were 400 people there waiting for me. The cement company was hosting a “thank you” barbecue for community supporters, and announced me as I pulled up and removed my bike helmet. The crowd, which had evidently been prepped on my stance, jeered loudly.

I never even got the Sierra Club endorsement. 

Lesson: Narrowcasting a message isn’t possible anymore. Especially in the camera-phone age of oppo, you can’t say one thing to one audience and expect another constituency not to find out. 

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About a month before Election Day, I marched in the Pride Parade celebrating the LGBTQ community. A gaggle of men insistently beckoned me, so I went over to shake their hands. 

“Are you single, Jeff?” one called out, and they all cheered. 

Though straight, I was, indeed, single. So I laughed, waved my bare ring finger at them, and kept walking, while they hooted gleefully. In the moment I figured, “What the hell? If they think I’m gay, maybe that wins me a few more votes.”

Shortly thereafter, people started gossiping.

Also on the ballot that cycle was a constitutional amendment banning gay marriage. Most of the candidates in our 10-way Democratic primary supported the ban. I vocally opposed it. 

The district contained three main sections: St. Louis city (which generally supported gay rights), St. Louis County (which was mixed) and rural/exurban areas an hour south (which was generally opposed). 

The Saturday before Election Day, an anonymous flyer hit the rural/exurban part of the district. “JEFF SMITH SUPPORTS GAY MARRIAGE!” it screamed, alongside a photoshopped picture of me and a gay man. “Ever wonder why?”

Though I won St. Louis city and County, I managed just 8% in the district’s southern third, costing me the race. I lost by 1%.

Lesson: Don’t pretend to be something you’re not. 

This lesson is particularly applicable to Missouri’s 2022 U.S. Senate field, in which some very smart men are pretending to be stupid because they think it will help them win.

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I came back two years later and won a state Senate primary to represent St. Louis city. I was named to chair the Senate Democrats’ campaign arm… another rich opportunity to screw up.

In one key swing district, local party leaders hailed a “rock star” prospect who they deemed the only one capable of beating the incumbent. We met for coffee, and she asked what the ballpark budget would be.

“Three-quarters of a million,” I said.

“And will that all come from you,” she asked, “or am I expected to raise some?”

Lesson: I should’ve immediately stopped recruiting her. Any candidate who thought a universe existed in which a party raised all her campaign money would never work hard enough to win. She lost badly.

—

A second targeted race that cycle featured an actual rock-star candidate waiting in the wings – a handsome, articulate young county prosecutor with deep roots in the rural district and well-heeled connections across the state.

The problem? He insisted on a clear primary field. And a no-name candidate — the self-proclaimed “only Pakistani man in Saline county” — had already filed. I needed to fix that.

I drove up to Marshall to meet with the man, a local community college adjunct professor.

“So,” I asked, “what’s motivating you to do this?”

“Health care,” he replied.

“I understand. It’s a huge issue after the Medicaid cuts here, and also nationally, with 40 million uninsured peo—”

“No, no, no!” he interjected. “Benefits! I need ze benefits!”

I could not persuade him that he was the longest of longshots — highly unlikely to ever obtain a state health insurance plan.

Lesson: When you want to get somebody in or out of a race, you need to understand their motivation and be prepared to address their needs. 

Mitch McConnell may want to remember this lesson before his lieutenants intervene to narrow the Missouri Senate field. 

The GOP leader hopes to hold Roy Blunt’s Senate seat, and he’s telegraphing his concern that Eric Greitens could endanger the seat since the disgraced former governor likely benefits from a fragmented field. 

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Of course, the mistake for which I’m best known is one that changed my life irreparably.

So let’s go back to my 2004 congressional bid. 

A few weeks before Election Day, a shadowy operative approached two of my aides. He wanted to produce a postcard highlighting my opponent Russ Carnahan’s dismal state legislative attendance record. I was pretty sure campaigns couldn’t legally coordinate with an outside group. I also figured it happened every day, without consequence. 

My aides asked me if they should move forward.

Whatever you guys do, I don’t wanna know the details. Understand?

They nodded. We agreed to never speak of the matter again.

In the campaign’s final week, the 3×5 postcard dropped, featuring Carnahan’s face on a milk carton. “MISSING: RUSS CARNAHAN,” it read, and detailed his absenteeism. 

The design was totally amateurish — a joke, really. We laughed and shook our heads. But Carnahan filed a complaint with the Federal Election Commission, alleging that my campaign illegally coordinated with the postcard’s producer. I signed an affidavit denying any knowledge of coordination. 

Five years after losing that election and three years into my Senate term, my then-best friend engaged me in months of conversation about the 2004 race, getting me to admit knowing of the coordination. 

During those months, he was wearing a wire.

The Feds contended that I masterminded a “textbook case of political corruption.” I pleaded guilty to obstruction of justice for impeding the investigation Carnahan’s complaint had spurred, and was sentenced to a year and a day in federal prison.

Lesson: Just say what you want to say about an opponent. Don’t play footsie with a third party group. Coordinating any expenditure is a federal crime — and so is covering it up. 

A similar issue could confront Greitens, given his own campaign’s paltry fundraising compared to the $2.5 million raised from a Wisconsin billionaire into a supportive third party committee able to accept unlimited donations.

With 25 times as much cash in the purportedly independent committee as he has in his own campaign committee, the renowned micro-manager will be tempted to try and influence the flush outside group’s advertising. As a fellow control freak candidate, I understand the impulse.

I also understand the potential consequences as well as anyone, and I hope any candidate in a similar scenario will use my experience as a cautionary tale.