[1][2][3] The Enterprise, or Enterprize, with an engine and power train designed and built by Daniel French, was launched before June 1814 at Brownsville for her owners: the shareholders of the Monongahela and Ohio Steam Boat Company.

On December 2, General Andrew Jackson had marched from Mobile, Alabama, to New Orleans with orders to oppose an imminent military invasion by an overwhelming British force.

[8][12][13] Command was transferred to Henry Miller Shreve, a Brownsville resident and experienced keelboat captain, who had firsthand knowledge of the hazards to navigation of the Ohio and Mississippi Rivers.

[14] On December 21, 1814, the Enterprise departed Pittsburgh bound for New Orleans with a cargo of "Cannon-balls, Gun-Carriages, Smith's Tools, Boxes of Harness, &c".

[19][20] However, the Enterprise was protected from the monopolists and free to navigate the state's waters by the martial law imposed by General Andrew Jackson on December 16.

[34] Sheriff John H. Holland, acting on orders issued by the court, quickly arrested Henry Shreve and seized the Enterprise.

On May 2, attorney Abner L. Duncan, representing the shareholders of the Monongahela and Ohio Steam Boat Company, posted bail and made arrangements for Shreve and the Enterprise to be released.

[43] On January 25, the Enterprise "with a full cargo of flour, whiskey, apples, &c. and a number of passengers" departed Shippingport bound for New Orleans.

[57] Duncan argued that this federal patent protected all of the defendants – French, Shreve and the shareholders of the Monongahela and Ohio Steam Boat Co. – from the charges by the monopolists.

[58] On May 20, Judge Hall, stating that the Territorial Legislature had exceeded its authority in granting the steamboat monopoly, dismissed the petition of the plaintiffs.

A letter announcing the news of Judge Hall's decision and proclaiming its significance to the growth of steamboat commerce and the economy of the West was published in a Louisville newspaper.

[62][63] Historian Thomas Shourds utilized firsthand information provided by Elisha Hunt, the principal founder and shareholder of the Monongahela and Ohio Steam Boat Company, to chronicle the final days of the Enterprise: "The Enterprise finally reached Shippins Port, below the Falls of the Ohio river, and the river being low above, and freights dull, the Captain anchored the boat in deep water, and hiring two men to take care of her, went by land to Pittsburg.

One of the men went ashore and the other got drunk and neglected the pumps, the weather was hot, the seams of the boat opened, and the Enterprise filled and sank to the bottom, where, as Elisha Hunt, in a letter written in the year 1851, says 'she still is.'

"[64]During August or early autumn of 1816, the Enterprise, while safely anchored in Rock Harbor, "filled and sank to the bottom" where, in the words of Elisha Hunt, "she still is."