The first legal challenge to the indenture was filed in July, 1865 by a Black business man named Tabbs Gross, during an engagement Tom had in Indiana, claiming that he had a bill-of-sale for Tom's services. James Bethune and his two sons quickly left the state with Wiggins, but Gross followed them to Cincinnati and filed a Writ of Habeus Corpus against them. Professor Southall continues the story:
As was revealed in my first book of the Blind Tom series (Minneapolis: Challenge Productions, Inc., 1979), this historic "guardianship trial," which was held before Judge Woodruff of the Hamilton County Probate Court, had both political and racial overtones, and ended with the judge's decision to allow Bethune, an ex-slave owner, to keep Tom in a "neo-chattel" relationship. Inasmuch as the guardianship agreement permitted the Bethunes to receive ninety percent of Tom's earnings with nothing to guarantee that they would not expropriate the ten percent promised to Tom and his parents, the trial offered one more example of how ex-slave owners were able to re-enslave their slaves, the Emancipation Proclamation notwithstanding.
In the July 25th, 1865, Cincinnati Enquirer, the editor, speaking to the humane aspects of the decision, asked: "why is Tom compelled to support Bethune and his two able-bodied sons who, fresh from the ranks of treason, are making the tour of the North with abundant leisure and purses well filled by the talents of what they would have us believe, an idiot? Why don't they go to work?'