In May 2023, Chicago developer Scott Goodman's business Sterling Racine LLC had fallen so far behind in its rent for space in a CTA-owned West Loop building that the transit agency began pressuring the company to pay up. As that debt grew to millions of dollars — in addition to its unpaid property taxes on the taxpayer-owned building at 120 N. Racine Ave. — Goodman, the company’s top executive, still was making campaign contributions to Cook County Board President Toni Preckwinkle and other politicians.Those campaign contributions included $1,500 Goodman gave to Preckwinkle on May 16, 2023, elections records show.Around the same time, Goodman made contributions to Chicago City Council candidates running to represent the 4th Ward — the area of the South Side that’s home to the old Michael Reese Hospital, which another Goodman company wants to develop with taxpayers' financial backing, perhaps as a stadium for the Bears. The team has expressed little enthusiasm for the Michael Reese site. Goodman, a real estate developer whose Farpoint Development LLC is based at the CTA-owned West Loop building that also houses the agency’s control center, gave $1,500 to Prentice Butler’s unsuccessful City Council campaign on Feb. 13, 2023.On Feb. 14, 2023, Goodman gave $1,000 to Lamont Robinson, who ended up winning the 4th Ward seat.Goodman gave another $500 to Robinson on Feb. 27, 2023, and $5,000 more on March 30, 2023, according to Illinois State Board of Elections records that show all of that money to Robinson was refunded to Goodman within months. Related The DNC’s deadbeat Chicago landlord This year, as Sterling Racine LLC lagged in getting caught up with its overdue government bills, Goodman made campaign contributions to two Democratic state legislators who represent the area that includes the Michael Reese site. He gave $1,500 on June 30 to state Rep. Kam Buckner and $1,500 on Sept. 11 to state Sen. Robert Peters. The CTA-owned building at 120 N. Racine Ave.Tyler Pasciak LaRiviere / Sun-Times In March, Goodman gave $1,500 to Illinois Secretary of State Alexi Giannoulias and $1,000 to Ald. Pat Dowell (3rd).As of May, Sterling Racine LLC owed the CTA nearly $2 million in rent. It was caught up as of Sept. 30, according to the CTA, but the transit agency says the Goodman company still owes $25 million in late fees. It’s unclear how that’s being resolved. Goodman’s lease for the CTA property expires Aug. 31, 2025.His company stopped paying the property taxes on the CTA property two years ago and is more than $1 million in arrears, records show.Goodman says his company, which recently changed its name to Randolph Racine LLC, "has honored its agreement and per the CTA is now current and in good standing and late fees are under discussion."Randolph Racine acknowledges it has fallen behind on real estate lease taxes due to vacancies caused by the pandemic but has made arrangements to become fully current."Asked about his campaign contributions, Goodman says, "We support the communities we work with in many ways and we believe in supporting those who share our values, like inclusion, health equity, workforce development, education, minority employment, minority small business development, job creation and access to public transportation."Even while Sterling Racine LLC has been stiffing taxpayers, it was making money this year by renting part of its space at the CTA building on Racine to organizers of the Democratic National Convention, held in August at the United Center, about a mile west of the building.Convention organizers said they weren't aware that the CTA had been hounding Goodman to pay the rent. These are among recent campaign contributions from developer Scott Goodman.Illinois State Board of Elections Goodman also has been involved in other lucrative deals with government agencies.Last April, the DuPage Water Commission paid Goodman and a partner $80.5 million for the former Green Acres Golf Club in Northbrook, hoping to build a water treatment and distribution plant on the 127-acre site, records show. Goodman’s group had bought the property for $9.7 million six years ago.Another Goodman company paid $40 million last December to buy a vacant commercial building at 830 N. Michigan Ave., across from Water Tower Place. The tax bills are mailed to Farpoint’s offices on Racine — the building where it's behind on property taxes. Related Chicago’s deadbeat migrant shelter landlords get millions from City Hall despite tax troubles, government debts Goodman also owned three buildings that City Hall leased to house migrants: at 1308 N. Elston Ave., 2241 S. Halsted St. and 344 N. Ogden Ave. Those three facilities, which had a total 4,300 beds, made Goodman the city’s biggest migrant landlord.Goodman and his partners bought the Halsted warehouse for $4.5 million in August 2023, weeks before City Hall began using it to house migrants.City Hall paid Goodman and his partners $12.3 million to lease those buildings between September 2023 and May, records show. The city recently stopped housing migrants at Goodman’s properties on Halsted and Ogden.