Back in private life, he started two newspapers in Washington, D.C., but both ceased operations shortly after opening. Throughout the 1840s, Kendall was the subject of numerous lawsuits from postal contractors who sued him for damages over his manipulation of Post Office operations. While in office, Kendall lost one Supreme Court decision. He had refused to honor a contract for mail delivery signed by his predecessor, even though Congress had enacted legislation requiring him to do so. Kendall said the legislation was an unconstitutional infringement on the executive branch. In "Kendall v. United States ex rel. Stokes", 37 U.S. 524 (1838), the Supreme Court disagreed. But in "Kendall v. Stokes", 44 U.S. 87 (1845), the Supreme Court held that Kendall was not personally liable for the debt owed, saving him from incarceration in debtors' prison.