Power struggle delays filling one of Chicago’s most important and highest paid jobs — Choose Chicago CEO

Aside from Chicago’s mayor, there is no job more important to the city’s economic future than the head of the convention and tourism agency known as Choose Chicago.

Yet the permanent job that has commanded an annual salary of $520,000 has been vacant for more than a year amid a behind-the-scenes power struggle that pitted allies of Mayor Brandon Johnson against the city’s business and labor leadership.

Now Johnson’s allies have abandoned their months-long push for Deputy Mayor Kenya Merritt to get what is believed to be the highest paid public job in Chicago.

Johnson has met with and signed off on the hiring of Kristen Reynolds, who has spent the last decade as CEO of Discover Long Island. Choose Chicago has yet to formally announce Reynolds’ hiring.

Discover Long Island has a budget that pales by comparison to Choose Chicago’s. But Reynolds is a 27-year veteran tourism professional with experience to fend off hard-charging competitors like Las Vegas, Orlando and New York.

Her resume includes stints at the Arizona Lodging & Tourism Association, the Arizona Office of Tourism and the Sheraton Wild Horse Pass Resort & Spa.

In a statement to the Sun-Times, the mayor’s office insisted that Johnson “never lobbied on behalf of any candidates for Choose CEO or instructed anyone to lobby on his behalf for anyone.”

“Mayor Johnson fully appreciates the critical role that tourism and conferences play in Chicago’s economy, which is why he wanted to make sure that the search committee found the best possible candidate to run Choose Chicago,” the mayor’s office said in a statement.

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Several sources familiar with the marathon search said there’s more to it than that.

They asserted that Johnson allies spent months lobbying behind-the-scenes for Merritt, deputy mayor for economic and community development.

The search process dragged on because there was heavy resistance to Merritt on the smaller search committee and on the full, 34-member Choose Chicago board that includes heavyweights from business, labor and government and appointees of both the mayor and Gov. JB Pritzker.

The resistance stemmed from the fact that Merritt is a career city bureaucrat with no background in the insular convention and tourism industry.

“He wanted to force the board to hire Kenya Merritt,” said a Choose Chicago board member. “This position requires a professional who knows tourism and travel. We have been a rudderless ship out in the ocean for many years.”

The board member said Johnson’s lobbying was “disrespectful to the city and completely disregards the board’s hiring process.”

Another source familiar with the search said Johnson “wanted an African-American CEO, but that’s not what you do with that job,” said a source familiar with the power struggle.

“You think you’re gonna keep conventions with somebody who has no experience running a huge, $50 billion convention business? No,” the source said.

Several insiders said Johnson’s campaign on Merritt’s behalf was led by a close ally in the business community, Charles Smith, CEO of CS Insurance Strategies. Smith also is vice chairman of World Business Chicago, which promotes the region for business growth.

Smith declined to discuss Merritt, emphasizing his respect for the Choose Chicago board and its process for choosing a CEO.

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In an email to the Sun-Times, Reynolds confirmed that she’s being considered for Choose Chicago but denied additional comment. Crain’s Chicago Business first reported that Reynolds is likely to get the job.

Reynolds would replace Rich Gamble, who has been holding down the fort since the January 2024 resignation of Lynn Osmond, a former president and CEO of the Chicago Architecture Center who resigned less than halfway through her four-year contract. Gamble is a former Brookfield Zoo executive. Prior CEOs at Choose Chicago came straight from the tourism sector.

The impending changing of the guard comes at a critical juncture.

Choose Chicago has been laying the groundwork to create a so-called Tourism Improvement District that would more than double the marketing agency’s annual budget by increasing the tax on room in Chicago hotels with 100 or more rooms by 1.5 percentage points — to 18.9%.

The Las Vegas Convention and Visitors Authority has an annual operating budget of $457 million, according to a comparison prepared by Choose Chicago. That’s followed by Visit Orlando ($116 million), Discover Los Angeles ($62 million), the San Diego Tourism Authority ($57 million) and New York’s NYC & Company ($45 million).

Choose Chicago is dead last among major convention cities with a projected budget for $33 million for 2024.

The COVID-19 pandemic shut down most of its tourism economy and smashed the five-day-a-week commuting habit of office workers. The city’s recovery since then has been gradual, with leisure and business travel bouncing back but many office workers still opting for remote work at least part of the time.

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Choose Chicago, which has yet to release data for 2024, said Chicago had 52 million domestic and international visitors in 2023. The number has increased steadily in recent years, but Chicago has struggled to match the 61 million visitors of 2019, the last full year before the pandemic. Worries about high taxes and crime hurt perceptions about Chicago as a place to visit or do business.

However, the city has scored many positive reviews — and drawn more visitors from the suburbs and the Midwest — by hosting such big events as Lollapalooza, NASCAR races, Taylor Swift concerts and last year’s Democratic National Convention.

The activity has helped the hotel industry, which has steadily raised average rates despite overall room demand that still trails 2019 figures, according to research firm STR.

Similarly, federal hiring data shows Chicago’s 372,000 leisure and hospitality jobs in 2024 are still less than the 2019 count.

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