Several surviving records suggest he periodically could not or would not pay his bills, and so he attempted to borrow money from wealthier acquaintances or, more often, simply defaulted on the obligation.

[7][a] In 1826, when Henry Clay was serving as U.S. Secretary of State, Pettis wrote him three different times asking for a patronage job; none was granted.

[1] In 1828 he and a partner named J. H. Lee were soliciting subscriptions for a 500-page biography of Founding Father Thomas Jefferson, who had died two years earlier at the age of 83.

He is an accomplished swindler; the subscriber is ready to prove him such, and therefore cautions the public against paying him any money, in advance, for the Herald which he represents he intends to publish.

[11]In December 1830, Pettis wrote to Henry Clay again, seemingly asking for help getting a newspaper editorship in a pro-Clay media market, volunteering his thoughts on the upcoming election, and describing Francis Blair's newly launched Washington Globe as a pro-Andrew Jackson periodical that sought to replace Duff Green as the official printer to the U.S. Congress: "A Jackson Member (supposing me to be with my Brother & the administration) stated to me that its object is to supplant Duff—that he is to be killed, and they mean to have the honor of doing it themselves.

After failed efforts to reach agreement with Cromwell on the debt and recover his property, Pettis swore an oath before justice of the peace William Hebb (c. 1789–1848) on October 24 that his possessions had been stolen.

In reply, the Globe on December 3 recapitulated the grounds of the pardon stated in this order, quoting from William Hebb's and Thomas Swann's letters to [Jackson] on November 14 and 15.

Cromwell wrote Globe editor F. P. Blair on December 17 that [Jackson] had 'been grossly imposed upon' concerning the facts of the case, and that Pettis was 'an imposter' and 'a most abandoned character' who had never intended to pay his board and whose presence had driven out his other boarders.

As a rule, Pettis would advertise in Southern papers, instructing "masters who desired his services...to forward him power of attorney, a description of the runaway, 'and also a fee of $20'.

[26] The group, nominally headed by New York City Recorder Richard Riker and Third Ward constable Tobias Boudinot, also included Daniel D. Nash (whom abolitionists identified as a "pimp for slave holders"),[25] John Lyon, and another Virginian, Edward R.

[27] As explained by historian Leslie M. Harris:[27] Nash, Lyon, Waddy, and Pettis acted individually or in concert as agents for slave owners, advertising their services in southern newspapers and seizing suspected fugitives on the streets of New York.

They then appeared before any federal or state judge, or more likely the local magistrate and known southern sympathizer Riker, to offer oral or written proof that the person was a slave.

In the words of historian Calvin Schermerhorn, "To most white Southerners, abolitionists were the witches and terrorists of their age: malignant, ubiquitous, and utterly real.

"[28] Pettis seems to have been acutely aware of this and by the 1840s was headlining his ads "ABOLITION" and advising his readers in the District of Columbia, "There are thousands of fugitive slaves in this city and its environs, and they continue to multiply rapidly.

[22] An 1842 article in the Green Bay Republican of Wisconsin suggested that Pettis was exploiting the anxieties of southern slave owners for his own gain, encouraging them to believe slave-stealing abolitionists were at work everywhere, but he promising could solve their problems if they would only send him US$20 (equivalent to $631.45 in 2023) in cash, from which he "has already raised a pretty handsome sum".

[31][25] Throughout 1843, Pettis was marketing something called the "Nassau Principle of Water-Proving Cloth," offering a local license for the waterproofing process to all comers.