The legal troubles for the owner of the now-defunct Oberg Roofing and Remodeling came to a head when he was arrested and jailed in Missouri on July 10 related to fraud charges.

According to reports from the SC Times, Caleb Oberg was arrested after an investigation by the Stearns County Sheriff’s Office revealed Oberg allegedly defrauded 23 customers out of nearly $240,000 from July 2023 to September 2024.

New details from the investigation allege that Oberg sold a company truck to buy a Corvette and told employees to lie to customers when the company suffered from financial troubles.

Oberg faces five felony charges of theft by swindle, each carrying up to 20 years in prison and/or a $20,000 fine.

According to KNSI radio, a warrant was issued on July 9. On July 10, Oberg was arrested in Christian County, Mo., and was being held on $50,000 bond. Stearns County officials are waiting to extradite him to Minnesota.

Caleb Oberg. Photo courtesy of the Christian County Sheriff's Office. 

The investigation was spurred after Oberg Roofing collected payments from customers but didn’t complete the jobs. In St. Cloud, Minn., homeowners, a roofing distributor and a contractor collectively filed 12 lawsuits against the roofing company, requesting a combined total of at least $714,750 in damages.

The lawsuit filed by the distributor said Oberg Roofing hadn’t paid overdue balances for building materials, though this didn’t stop the company from cashing customers’ checks as late as August 2024.

A criminal complaint claims Oberg had 53 open jobs with customers in September 2024. A month later, Oberg Roofing and Remodeling shuttered its business. Investigators spoke with customers, all of whom said they signed contracts and paid Oberg but didn’t see the work completed.

Oberg filed for personal bankruptcy on May 8, according to court documents. He previously told the St. Cloud Times that a lack of new sales revenue caused the company to not keep up with the “unsustainable amount of overhead for the actual sales revenue we did get in 2024.”

The new findings, though, shed light on poor business decisions that may have led to money troubles.

The Stearns County investigation reports that a bookkeeper alleged Oberg sold a company truck in January 2024 to use as a down payment for a $160,000 Corvette. The bookkeeper told the investigators the actions came following a “slow year” on the books for Oberg Roofing.

The bookkeeper alleges that Oberg didn’t tell his business partner, Chad Whitcher, about the financial problems. Whitcher, who owned 40% of the company, told investigators that he became aware of the issue in early 2024 and learned from the bookkeeper that two of the company’s suppliers were no longer doing business with the company due to pending debts.

Whitcher said he believed the financial troubles started after Oberg bought a new office at 717 W. St. Germain St. in downtown St. Cloud, which he purchased for about $845,000, according to the Minnesota Department of Revenue.

Oberg reportedly used one account for all business transactions, according to the criminal complaint, despite the bookkeeper telling him to open a trust account for customer deposits. In May 2024, the bookkeeper told Oberg he needed to lay off employees, which he did in June 2024, though he allegedly told employees to keep selling.

It was around this time that the roofing suppliers sent lien notices to customers for unpaid bills owed by the contractor. When customers called the company asking about the notices, Oberg reportedly told employees to “make up a lie about why they were receiving them.”

This avoidance escalated when the company started locking the doors to its office in September 2024 to prevent people from confronting them in person. Court records allege Oberg told employees to “lie about why the doors were locked” as well, all while the company collected deposits from customers.

Oberg’s contractor's license was revoked on Nov. 7, 2024.