Mike Lindell's Chaska-based pillow company MyPillow made just two of 24 payments on an $800,000 debt to the delivery company DHL, according to a lawsuit filed in Hennepin County this week.

Documents attached to the lawsuit show that DHL signed an initial customer account agreement with MyPillow in 2015 for an estimated yearly spend of $4 million on delivery of their pillows with all payments being made within 15 days of delivery. The companies entered into a new agreement last year for MyPillow to pay off a debt of $818,493 with monthly installments of $32,291.67 starting in April 2024.

MyPillow made the first two payments of that settlement for $64,583.34, with the most recent payment on June 6. Lawyers for DHL alerted MyPillow in early July that they would begin legal proceedings if a payment was not received within five business days.

The suit is seeking the principal debt amount of $799,925.59, plus 18% annual interest and attorney fees.

MyPillow and Lindell have been at the center of several lawsuits in recent years that have impacted the financial viability of the company, including three federal defamation lawsuits related to Lindell's disproved claims of a stolen 2020 presidential election. The largest lawsuit, brought by Denver-based voting machine company Dominion, is seeking $1.3 billion in damages.

In 2023, Lindell told the Star Tribune, "I would never settle in any lawsuit. You don't settle for something where you've done nothing wrong."

MyPillow was facing eviction from its Shakopee outlet store, warehouse and primary manufacturing plant earlier this year, but the landlord dropped the case after MyPillow paid nearly half a million dollars in overdue rent in July.

A federal judge in St. Paul ruled in February that Lindell owed $5 million to a man who entered a contest Lindell created called the "Prove Mike Wrong Challenge" in which he challenged anyone to prove that his data regarding election fraud was not valid. Robert Zeidman, a computer expert from Nevada, entered the challenge. While Lindell and a panel of judges denied his entry, a panel of three arbitrators ruled he had satisfied the contest rules and had to be paid the prize money. Lindell plans to appeal.

This is not the first lawsuit against MyPillow alleging breach of contract over delivery-related expenses. Extend Inc., a California company that provides shipping and product protection services, sued MyPillow this year in U.S. District Court for the Northern District of California alleging that the company owes them $564,151.39.

Lindell has been diversifying his business portfolio and recently took his FrankSpeech media platform public through a merger with a holding company. Lindell founded FrankSpeech and later its social media counterpart, FrankSocial, in 2021 after Twitter kicked him off the platform for repeating unproven election fraud claims.

Star Tribune staff writers Brooks Johnson and Briana Bierschbach contributed to this story.