The last time Jeff Larson agreed to help with the Republican National Convention, he inherited a bankruptcy and ended up paying for Sarah Palin’s new wardrobe. He must have thought that was as hard as it gets in convention planning.

This year, Larson is back. He’s the convention’s CEO and is forced to deal with some frustrated Republicans and donors inside the party who don’t want Donald Trump to be the GOP nominee and protesters outside the security perimeter who want to burn the whole thing to the ground.

In 2008, when the Minneapolis-St. Paul host committee was struggling to raise money before the national convention, Larson stepped in as chief executive officer and is credited for getting it back to financial stability. The committee ended up with a multimillion dollar surplus it donated to three area nonprofits but Larson still ended up in the red.

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Shortly before the Republican National Convention began, someone thought the presumptive GOP nominee for vice president/governor of Alaska needed new clothes and had the idea that the host committee pay for them.

Larson said no to that, but scratched his personal credit card number and expiration date on a scrap of paper to help the cause. He had almost forgotten about it until he received a bill of more than $130,000 in charges (for which the Republican National Committee infamously reimbursed him).

“No two conventions are alike and no two cities are alike,” Larson said about the logistics. Eight years ago was challenging because many of the hotels, restaurants, and bars were in Minneapolis while the convention was in St. Paul.

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Cavaliers boxed out convention

This year, the festivities are consolidated to Cleveland, but the event is nearly seven weeks earlier and the Cleveland Cavaliers’ extended playoff run to the NBA championship delayed the convention committee’s ability to prep the Quicken Loans Arena.

“It’s the shortest time we’ve ever had to move in, and put a parade in the middle of it,” Larson added, talking about the team’s celebratory trip through downtown that drew more than a million fans.

But this certainly isn’t the first time Larson has been in the middle of the political action.

Later in the 2008 cycle, he became part of Republican Norm Coleman’s 2008 re-election campaign. The senator actually lived in the basement of Larson’s D.C. townhouse, their rental agreement became one part of the campaign narrative and Coleman ended up losing to former “Saturday Night Live” comedian Al Franken.

Larson didn’t quite avenge that loss, failing to defeat Franken in 2014 when he ran the National Republican Senatorial Committee’s multimillion dollar independent expenditure arm. But he and the Republicans gained nine seats and the Senate majority.

He brings three decades of political experience to the convention planning process from volunteering for his hometown mayor in Grand Forks, North Dakota, to being part of the largest telemarketing firm on the Republican side.

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Larson got his political feet wet volunteering for newly elected Grand Forks Mayor H.C. “Bud” Wessman, who lost his bid for the Senate in 1982 at the state GOP convention to Gene Knorr. But a couple of weeks later, Larson was hired by the Knorr campaign.

“I was the driver and within two weeks, I was finance director,” he recalled about the race in which he made $800 per month. “That tells you something about the campaign,” he said with a smile.

Knorr fell short of knocking off Democratic incumbent Quentin Burdick, 63 to 34 percent, but the cycle wasn’t a total loss. Larson met his future wife, who was working for congressional candidate Kent Jones. And after Jones lost to Democrat Byron Dorgan, he hired Larson as marketing director at the state Department of Agriculture.

Getting back on the trail

It didn’t take long before Larson got back on the campaign trail. In 1984, he worked on Republican Gov. Allen Olson’s unsuccessful re-election campaign. The next cycle, Larson was the Bismarck-based western field coordinator for the National Republican Congressional Committee, which is in charge of electing House members for the GOP.

“He’s probably a pretty boring guy to write a story about,” quipped Republican media consultant Curt Anderson of OnMessage Inc. The two men met in 1986 when Anderson was working with Republican Dale Bell in an open-seat race for South Dakota’s at-large House seat. “So many people have an act or a schtick,” Anderson added, “He’s an even-keeled, regular guy.” That’s a common refrain from the people who have worked with Larson.

In 1988, Larson moved 1,500 miles east to become executive director of the Delaware Republican Party. It was much more exciting back then when The First State was still competitive and wealthy Pete du Pont’s presidential campaign was housed next door, leading to a well-equipped party headquarters.

Two years later, Larson moved to Minneapolis to become regional political director for the West for the RNC, before transitioning to President George H.W. Bush’s re-election campaign.

Eventually Larson found himself traveling to Wyoming three weeks before the 1992 election. “You know things aren’t going well,” he joked. “You learn more when you lose than when you win.” From that race, Larson learned about the importance of locking up your base vote as independent Ross Perot gained some late traction in western states.

A wife, two kids and no job

The day after the election, Larson woke up with a wife, two kids, and no job. He eventually got a job with Strategic Telecommunications. And in 1999, Tom Synhorst brought him together with Tony Feather to form FLS, which grew into the largest telemarketing firm on the Republican side, assisting campaigns with calls for microtargeting and fundraising.

Larson eventually moved to Hudson, Wisconsin, just about 20 minutes from St. Paul across the St. Croix River, where you’ll find him drinking a gin and tonic when the Cleveland convention is complete.

Larson first met Coleman, then a Democrat, when he was running for re-election as mayor of St. Paul. Larson’s wife later went to work for Republican Sen. Coleman and Larson eventually become a fundraiser and close adviser.

FLS worked on Coleman’s 2002 Senate race and, the following year, Larson founded Coleman’s NorthStar Leadership PAC. Now, Larson is on the board of the American Action Network, where Coleman serves as chairman.

Larson and his bank account survived the 2008 convention and election cycle and after the 2010 elections, he sold his stake in FLS Connect in order to play a different role in the party.

When Wisconsin Republican Party Chairman Reince Priebus became RNC chairman, Larson followed him to Washington to become chief of staff. The party was coming off major gains in the 2010 elections but was also more than $20 million in debt. When Larson left a few years later, the committee had more than $5 million on hand.

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“What I like about Jeff is that he is unassuming,” Priebus said. “He’s not a show pony.”

He might not be a show pony but Larson does have an ongoing horse racing hobby that goes back at least 15 years. Owning horses, such as Tubby Time, has taught Larson a bit of patience over the years.

That might come in handy when organizing an event with Donald Trump as its star.