The political newcomer – a restaurant owner running for mayor of one of Colorado’s largest cities as a moderate, pro-business outsider in a wide field of seasoned candidates and civic insiders – began the race as an affable underdog but confounded observers by finishing first in the general election and going on to win the runoff by a wide margin, defeating an established municipal officeholder.

Voters of all stripes flocked to the dark horse once it became clear he had a shot in the nonpartisan race. The swelling momentum was understandable in hindsight, in part because the early frontrunners had spent months tearing each other down and driving up their negatives, all while mostly ignoring the longshot candidate, leaving his image untarnished.

By the time ballots were counted, it was clear the city was ready for a different approach as the term-limited incumbent – a veteran politician with decades of public service under his belt – prepared to hand over the office of mayor to his successor.

The year was 2003, and the newly elected, fresh-faced mayor was brewpub owner John Hickenlooper, the entrepreneur and civic activist who charmed Denver voters with his talk of an inclusive, business-friendly approach to governing a city inching its way back from an economic downturn. Hardly anyone gave him a chance of winning when the former geologist launched his campaign to succeed outgoing Mayor Wellington Webb, joining a field already crowded with experienced politicians.

But a series of twists and turns, coupled with an electorate ready to chart a new course, propelled the unconventional candidate to a convincing, double-digit win over career politician Don Mares, who had served the previous two terms as the city’s auditor after a lengthy tenure in both chambers of the General Assembly.

As readers have no doubt realized, the above particulars could as easily describe this week’s election in Colorado Springs, when entrepreneur and civic activist Yemi Mobolade, a Nigerian immigrant and former pastor, trounced career politician Wayne Williams, a former county commissioner, county clerk, Colorado secretary of state and at-large city council member, to become the city’s first elected Black mayor.

With his business-friendly message of bringing everyone to the table, the unaffiliated candidate rode over fractures in the local Republican Party that hampered his runoff rival, emerging from relative obscurity in a packed first round and is now set to take over next month from outgoing Mayor John Suthers.

The parallels across two decades between the two Coloradans’ first runs for public office are uncanny, though there are differences between the candidates and the elections that swept them into office.

Both founded and ran restaurants before making their first runs for office. After being laid off from his job as a petroleum geologist, Hickenlooper kicked off Colorado’s brewpub craze when he opened the Wynkoop Brewing Company in Denver’s Lower Downtown, and by the time he ran for mayor had grown his culinary empire to seven restaurants. Mobolade co-owns Wild Goose Meeting House and Good Neighbors Meeting House in Colorado Springs.

Both set up nonprofits – Hickenlooper’s social-justice oriented Chinook Fund and Mobolade’s gospel-oriented COSILoveYou. Both had experience stoking business development, though Hickenlooper’s activities, which earned him the nickname “the mayor of LoDo,” were less structured than Mobolade’s job as vice president of business retention and expansion for the Colorado Springs Chamber & EDC.

Neither was a stranger to city affairs when he got in the race. Hickenlooper led the charge in 2000 to stop the Denver Broncos from discarding the phrase “mile high” when the city built a replacement football stadium. He argued the name was marketing gold for Denver, though he only scored a partial victory with a naming-rights sale yielding the moniker Invesco Field at Mile High. Mobolade took a more formal approach with a stint as small business development manager for the city of Colorado Springs.

The two elections were for open seats, with Webb finishing the third term permitted for Denver mayors and Suthers finishing his allotted second term. Before their elections as mayors, Webb was city auditor and a former state lawmaker and federal appointee, while Suthers was a former Colorado attorney general, district attorney and U.S. attorney for Colorado.

Like many of their first-round rivals, Hickenlooper and Mobolade campaigned on using their business smarts to rev up the local economy in the wake of fiscal slumps, with Denver still recovering in 2003 from the dot-com bust and Colorado Springs still getting past the effects of the global pandemic in 2023, as a historic drought put a spotlight on water issues in both elections.

Hickenlooper and Mobolade emerged from crowded first-round fields and headed into their runoffs with big leads over Mares and Williams, the respective second-place finishers, according to numerous public polls in the Denver race and internal polling made available to Colorado Politics in the Colorado Springs race.

The dynamics in both first rounds were similar, as the candidates perceived as the early leaders trained fire on each other while Hickenlooper and Mobolade quietly gathered steam, until it was too late for their surviving opponents to change voters’ favorable attitudes toward the likable outsiders.

In Denver’s 2003 race, the seven mayoral hopefuls in the general election – six Democrats and one former Democrat – also included early frontrunner Ari Zavaras, a former Denver police chief and one-time director of the state’s prison system, as well as former state Sen. Penfield Tate III, former City Councilwoman Sue Casey, businesswoman Elizabeth Schlosser and former state Democratic Chairman Phil Perington, who had later dropped his party affiliation.

Mares and Zavaras duked it out, with Tate lobbing some attacks of his own in the months leading up to the initial vote. Meanwhile, Hickenlooper captivated voters with a pair of humorous TV ads that began airing while the city was buried by a snowstorm, in one spot trying on different outfits at an iconic Denver Western wear retailer in order to “look more mayoral” before declaring that he wasn’t a politician and then riding away on a scooter.

By the time the first vote rolled around, Hickenlooper had won endorsements from both of Denver’s daily newspapers and nearly avoided a runoff.

The packed roster of 2023 Colorado Springs mayoral candidates numbered a dozen, also including Williams’ fellow early frontrunner Sallie Clark, a former city council member, county commissioner and federal appointee, plus former county commissioner and 2016 GOP U.S. Senate nominee Darryl Glenn, El Paso County Commissioner Longinos Gonzalez Jr. and outgoing at-large City Councilman Tom Strand. Those without backgrounds in elected office were Andrew Dalby, Lawrence Joseph Martinez, Christopher Mitchell, Jim Miller, Kallan Reece Rodebaugh and John “Tig” Tiegen.

Leading up to the general election, Williams and Clark piled on each other, aided by deep-pocketed developers who took sides based on a water ordinance supported by Williams that his critics believed favored one developer, leaving the others high and dry. The no-holds-barred battle exploited sharp divisions within the county GOP, which Williams chaired a generation ago but has been riven with infighting for years, leaving Williams on the losing side of a recent power struggle.

While he’s hardly the progressive liberal portrayed in ads Williams ran throughout the runoff, the unaffiliated Mobolade stood out as an independent in a field otherwise entirely populated by Republicans in a city that has recently begun shifting toward the center after decades as the deepest red Republican stronghold in the state.

Following the bitter first round, Clark, who finished just behind Williams in third place, was joined by other prominent Republicans throwing their support behind Mobolade, helping neutralize Williams’ attacks and, from the looks of the results, giving a green light to a share of GOP voters that it was OK to take a chance on the political novice.

In the final, unofficial vote, Mobolade scored a decisive win with 57% of the vote, not too shy of Hickenlooper’s 65% landslide.

Hickenlooper was reelected to a second term in 2007. In 2010, he won the first of his two terms as governor and mounted a brief presidential campaign in 2019 before winning election to the U.S. Senate in 2020.

At that point, the two Coloradans’ stories diverge, because Mobolade’s remains to be written.

Ernest Luning has covered politics for Colorado Politics and its predecessor publication, The Colorado Statesman, since 2009. He’s analyzed the exploits, foibles and history of state campaigns and politicians since 2018 in the weekly Trail Mix column.