CHICAGO — Last summer, former U.S. Rep. Luis Gutierrez said Mayor Rahm Emanuel offered up a political plum for Gutierrez’s daughter — he would appoint her alderman in the 30th Ward and find a new job for the sitting alderman.

Jessica Gutierrez, if appointed to the $120,383-a-year job in advance of the 2019 election, would then have a leg up on anyone else who might run for the seat in February.

Under the deal, Ald. Ariel Reboyras, the current 30th Ward alderman, would resign and get a top job in the city’s Aviation Department, the former congressman told Block Club Chicago.

But Jessica Gutierrez said she rejected the deal, which she said made her cringe. She wanted to win the seat herself, and decided to challenge Reboyras in the 2019 election, she said. Instead of walking away victorious, however, she managed to push him into a runoff election, only to lose to the veteran alderman Tuesday.

Jessica Gutierrez brought up the alleged plan to a reporter in the wake of her Tuesday night defeat to Reyboras. Her father, a former alderman who went on to serve 26 years in the U.S. House of Representatives, backed up her claim, saying Emanuel pitched the idea to him last summer.

A spokesperson for Emanuel, however, said the conversation never took place.

“I can categorically deny this conversation took place, or that any such deal was offered,” Emanuel spokesman Matthew McGrath said.

The elder Gutierrez, an on-again, off-again ally of Emanuel’s (they’re currently off), claims the promise was made during a riverside lunch meeting at River Roast, on a warm Sunday last summer.

In an effort to protect Reboyras — one of his most loyal and ardent supporters, who voted with him more than 96 percent of the time — and to quell potential conflict between himself and the Gutierrez family, Emanuel said he wanted to give Jessica Gutierrez the seat, Luis Gutierrez said.

But his daughter said she wasn’t interested.

“To be appointed by a mayor that has left the city in such distress? No, thank you,” she said. “That would be me aligning myself with everything that I am ideologically and fundamentally against.”

Jessica Gutierrez campaigned to unseat Ald. Ariel Reboyras (30th). Facebook/Provided

Reboyras went on to beat Jessica Gutierrez with 51.9 percent of the vote in Tuesday’s runoff election. The longtime alderman did not return messages left at his office and did not return phone calls or text messages to his phone about this story.

Luis Gutierrez said he wasn’t surprised Emanuel denied the allegations.

“This is the guy who paid $5 million to Laquan McDonald’s family,” Gutierrez said. “This is from Emanuel. This is what he does.”

Fear of a ‘changing electorate’

The allegations from the Gutierrez family are just the latest in a series of ups and downs between the two political powerhouses.

In October, the Sun-Times laid out the timeline of the Emanuel-Gutierrez saga:

Before he became mayor, Emanuel served as President Barack Obama’s chief of staff. Then-U.S. Rep. Luis Gutierrez blamed Emanuel for standing in the way of immigration reform. In retaliation, when Emanuel left the White House to run for mayor in 2011, Gutierrez endorsed Gery Chico — not Emanuel.

Four years later, however, Gutierrez co-chaired Emanuel’s re-election campaign. The patched-up relationship followed the mayor’s decision to join Gutierrez as a champion of immigration reform.

The two men even traveled to Puerto Rico together in 2018 to see the damage caused by Hurricane Maria.

But the tides turned again as Emanuel went all in on re-electing Reboyras, who has helped push the mayor’s agenda on police reform.

‘Must see u this weekend’

The case of the 30th Ward seat began on April 11, 2018, when Luis Gutierrez texted the mayor that he had important news to share.



“Must see u this weekend.” he wrote.

That Saturday, Luis Gutierrez said he met the mayor for lunch in the West Loop, and the then-congressman broke the news that his daughter planned to run for office in the 30th Ward — where Reboyras had ruled since 2003.

Jessica Gutierrez had moved back to Chicago from New Orleans after the 2016 presidential election.

“I was just kind of giving him a heads up,” Luis Gutierrez said. “We kind of left it at that.”

A few months went by, and on Sunday, July 22, Emanuel and Gutierrez met for lunch at River Roast on North LaSalle Street, the former congressman said.

They sat outside, by the river, Luis Gutierrez said. He remembered ordering calamari.

The mayor began their meeting by confiding in Gutierrez an increasing anxiety about the country’s “changing electorate” celebrating a “new kind of left,” Luis Gutierrez recalled.

For example, he said: in New York, longtime Rep. Joe Crowley (D-NY) lost his primary to a young, progressive Latina woman named Alexandria Ocasio-Cortez.

Then, the mayor launched into his plan to protect Reboyras, who was finishing out his fourth term and had closely aligned himself with Emanuel, Luis Gutierrez said.

Ald. Ariel Reboyras (30th) was first elected in 2003. Ariel Reboyras/Provided

First, the mayor said, he would move out Aviation Commissioner Ginger Evans, who had made aldermen “very unhappy,” Luis Gutierrez recalled.

Her removal would help clear the path for a well-paid position within the aviation department as head of security — a job that was “perfect” for Reboyras, given his experience serving as chair of the City Council’s Public Safety Committee, Luis Gutierrez said.

According to the mayor’s plan, Reboyras would have that high-powered job by early August — and Jessica Gutierrez would be appointed thereafter, and “in the seat” by Oct. 1, the former congressman said.

On June 19, news broke that Ginger Evans would step down as the city’s aviation commissioner, to be replaced by Jamie Rhee, who formerly served as the city’s chief procurement services officer, on Aug. 1.

Gutierrez said he reminded the mayor that while he had his support, his daughter was fervently against Emanuel.

She did not vote for him in the last election, and she pretty much stood for all the same progressive ideals that Ocasio-Cortez heralded in New York City.

“I said to the mayor, listen … she will never accept an appointment by you to the Chicago City Council,” Gutierrez said. “She didn’t vote for you four years ago. Jessica will only take the job if she’s elected.”

But what if there’s a vacancy, the mayor asked, according to the former congressman.

“I said, ‘Yes, but she’ll say no,'” Luis Gutierrez said.

Reboyras did not retire from City Council and take a job in aviation. (It is unclear whether Reboyras knew anything about Emanuel’s alleged promise to the Gutierrezes.)

Emanuel, as part of his push to get Reboyras re-elected, gave $20,000 to the Reboyras campaign in October 2018. He later gave another $25,000 to the veteran alderman’s campaign in March, which Luis Gutierrez said felt like a spiteful attack on his family and his daughter.

“We became at odds with each other when he decided he wasn’t going to be neutral,” Gutierrez said. “He can be a pretty mean and spiteful person. He took it personally.”

In the mayor’s mind, the father said, Emanuel may had thought that he offered Jessica Gutierrez a precious gift.

Jessica Gutierrez told Block Club that if she was going to lead, she had to win through the people — not the mayor.

“This is not a game,” she said. “These are the real lives of real people.”

Again, Emanuel’s office denies these conversations ever took place.

A tight race

Gutierrez launched her campaign in defiance of the mayor and drew an army of volunteers and supporters, many of whom were young people who wanted to unite the ward, she said.

Her pitch to voters was simple. As a progressive, anti-machine candidate, she promised to support a publicly-elected school board, enact a participatory budgeting strategy for the use of Tax Increment-Financing (TIF) districts and create more affordable housing.

She also promised something abstract: she told voters she could unite the rapidly gentrifying majority-Hispanic ward, which houses longtime Hispanic residents to the west and an increasing number of wealthier, white residents to the east.

After she pushed Reboyras into a runoff, relations between the two campaigns turned ugly.

Some 30th Ward voters received a text message that read: “Jessica Gutierrez’s daddy is trying to buy this election. Tell them we aren’t for sale! Re-elect Reboyras today!”

In response, Jessica Gutierrez accused Reboyras of “blatant sexism” in an interview with the Sun-Times.

Then, two days before the election, Jessica Gutierrez filed a police report against a Reboyras supporter named Esteben Burgoa, who had posted a 19-minute Facebook Live video in which he filmed himself circling the 31-year-old’s apartment.

In the video, Burgoa questioned the legality of Jessica Gutierrez’s 30th Ward residency. The Reboyras campaign shared Burgoa’s video in a Facebook post, which was later deleted.

At the end of the day, Jessica Gutierrez said the “sexist” messaging and “violent actions” toward her worked. The incumbent narrowly held onto his power.

Tears welled in Reboyras’ eyes as he declared victory in a tightly-packed Avondale bar, where a diverse crowd cited 15 years of clean streets and community-involved zoning decisions as the reason behind their support.

Some supporters, however, raised their glasses to what they saw as the real victory, yelling, “We beat Luis Gutierrez!”

Ald. Ariel Reboyras declared victory in the 30th Ward race. Hannah Alani/ Block Club Chicago

‘It’s not right’

A few days after the election, Jessica Gutierrez was trying to stay away from social media. Soon, she said, she’ll post publicly, thanking her volunteers and supporters for their efforts.

She promised them that she wasn’t going to stop fighting for a more progressive ward.

“I think we should be extremely proud,” she said. “We took on the machine and this time we didn’t win, but we definitely, definitely didn’t lose.”



Gutierrez told Block Club that she plans to unseat Reboyras as the 30th Ward’s Democratic Committeeman in 2020.

Until then, she will maintain her campaign office at 5518 W. Belmont Ave. — for as long as she can afford the rent — and use it as a space to register voters.

“If I was simply ‘daddy’s little girl,’ who was a pawn and a playing piece in the game, why would — why would I be working so hard right now?” she said. “I care deeply. It’s not right.”

Do stories like this matter to you? Subscribe to Block Club Chicago. Every dime we make funds reporting from Chicago’s neighborhoods.



