Less than a month ago, the Chicago Transit Authority — whose leaders are appointed by the mayor — announced a lucrative new contract with a company founded by prominent real-estate magnate Elzie Higginbottom.

Just a few weeks later, another company tied to Higginbottom gave a $50,000 contribution to a new political fund created by a close ally of Mayor Lori Lightfoot.

And on Wednesday, that so-called “independent expenditure” committee finally sprung into action, shelling out more than $70,000 to attack Cook County Commissioner Brandon Johnson, who’s one of Lightfoot’s main challengers in the Feb. 28 election.

A chain of events like this was supposed to have become a thing of the city’s notoriously corrupt, pay-to-play past more than a decade ago. Lightfoot and her immediate predecessor, Rahm Emanuel, vowed to follow ethics rules ostensibly designed to prevent incumbents from getting re-election help from companies that are gorging at City Hall’s massive trough of taxpayer-funded contracts.

But both Emanuel and Lightfoot have benefitted from gaping loopholes in the rules, which were intended to dispel the perception that mayors used their power to try to extend their stays on the fifth floor of City Hall.

The 77 Committee is the name of the fledgling effort by Lightfoot allies to bolster the embattled first-term mayor in the Feb. 28 election — often in ways she may not legally be able to do it herself.

The committee was created in October by Sean Harden, a developer and supporter of Lightfoot. He is the chair and treasurer of the 77 Committee, according to state election board records.

According to the fund’s filings with elections officials, the committee was “established to support strong, equitable and thoughtful leadership for Chicago in the municipal elections.”

The 77 Committee’s executive director, Dave Mellet, was a senior advisor on Lightfoot’s 2019 campaign but said his group in this election cycle did “not communicate or coordinate with any of the campaigns for mayor” and was solely responsible for how it’s raising and spending money.

As for the contributions detailed on the committee’s campaign finance reports, Mellet said, “Publicly disclosed campaign contributions are only reflective of the dates of deposit and are often weeks or months removed from the actual dates of receipt.

In a statement Friday, the Lightfoot campaign said she “is focused on her own campaign apparatus and has no control over any outside groups or organizations. Further, she and her team are legally prohibited from communicating directly with the entity in question on any strategic issue. If people want to join in any other efforts to support her agenda of making Chicago safer, fairer and more equitable for all – they are free to do so.”

But Lightfoot could disavow the group and publicly call on potential contributors not to give money to it, said Alisa Kaplan, executive director of Reform for Illinois.

“It’s not illegal, but it should be,” Kaplan said. “It’s unfortunate because obviously candidates know who’s donating to these independent expenditure committees.”

As a result, she said, “It can look like there’s a quid pro quo” when companies who do business with the city are funding the committee.

The money that’s gone to the pro-Lightfoot 77 Committee has been put to use a few weeks before the election, for an effort to oppose Johnson, one of the candidates who poses the biggest potential threat to the mayor’s re-election bid, according to a recent poll for WBEZ, the Chicago Sun-Times, NBC5 and Telemundo Chicago.

Johnson is supported by the Chicago Teachers Union, which frequently has clashed with Lightfoot since she took office four years ago.

The ads against Johnson cost the committee $71,332.50 and that money was paid to Beacon Media LLC of Washington, D.C. Although independent expenditure funds like the 77 Committee are supposed to operate separately from campaigns, records show Beacon Media played an important role in Lightfoot’s victorious run for mayor in 2019.

On the company’s website, that campaign touts the “iconic ads” it did for that landslide victory among its proudest “case studies.” The company took credit for Lightfoot’s “Bring in the light” campaign slogan and for TV spots touting her as the reform candidate among rivals with ties to the infamous Chicago political machine.

The 77 Committee has reported collecting a total of $210,000 — much of that money from contributors who do business with the city and could otherwise be prohibited from giving directly to Lightfoot’s re-election campaign.

The Chicago Tribune reported last year that the first two contributions to the committee, for a total of $100,000, came from donors with business ties to the city of Chicago.

The 77 Committee has collected another $110,000 since the start of the year, with the largest of the recent contributions coming from the company with ties to Higginbottom.

The contract approved on Jan. 13 allowed for the business, East Lake Management Inc., to cash in on the 5.6-mile extension of the CTA’s Red Line, where the agency plans to add four new stations between 95th and 130th Streets. East Lake Management could be paid more than $23.5 million to secure properties along the route of the extension, records show.

Less than three weeks later, on Jan. 31, another company at the same address as East Lake Management, a business called ELH Partners LLC, made the $50,000 contribution to the 77 Committee.

For Higginbottom — a former Illinois Gaming Board chairman who has been a major city contractor for decades — it’s not the first time that he has contributed significantly to a committee set up by allies of an incumbent mayor shortly before a crucial election.

In 2007, Higginbottom led a political fund to support City Council allies of then-Mayor Richard M. Daley who faced strong challenges from candidates funded heavily by organized labor. ELH Partners was a contributor to that committee also, according to campaign finance disclosure records.

ELH Partners had been a contributor to Lightfoot’s rival Toni Preckwinkle in the 2019 election, the records show.

Higginbottom did not respond to a message seeking comment Friday.

Another $5,000 was contributed to the 77 Committee on Jan. 31 by Christy Webber Landscapes, another politically connected company, which is based on the North Side.

That company appears on the city’s own list of companies that have been paid enough in the past four years by the municipal government and are consequently limited in their ability to contribute directly to Chicago’s elected officials under the city’s ethics ordinance.

Dan Mihalopoulos is an investigative reporter on WBEZ’s Government & Politics Team. Follow him on Twitter @dmihalopoulos.