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. The Enterprise, under the command of Israel Gregg, was first used to transport passengers and cargo to ports between Brownsville and Louisville, Kentucky. From June to December she completed two 600-mile (970 km) voyages from Louisville to Pittsburgh that were performed against strong river currents. With these voyages the Enterprise demonstrated for the first time that steamboat commerce was practical on the Ohio River.
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. Jackson had been making frequent requests for military supplies, especially small firearms and ammunition, which were in short supply. To this end, the shareholders made the decision to send the Enterprise. 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. 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". On December 28, the Enterprise passed the Falls of Ohio at Louisville, delivering the cargo of military supplies at the port of New Orleans on January 9, 1815.
Under normal circumstances, the voyage by the Enterprise into Louisiana's waters would have been a violation of the territorial steamboat monopoly granted to Robert R. Livingston and Robert Fulton. 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.
Despite the military supplies delivered by the Enterprise, Jackson's forces were still in dire need, particularly for small firearms, gunpowder and shot. Responding to reports that several boats laden with military supplies were near Natchez, Jackson sent the Enterprise. The boats were located and the Enterprise took them in tow, delivering them to New Orleans on January 26. Then the Enterprise made another roundtrip voyage to Natchez, followed by a trip via the Red River to Alexandria with 250 troops in tow.
On February 4, 1815, the British fleet, with all of the troops aboard, set sail for Mobile Bay. On February 16, the United States Senate ratified the Treaty of Ghent, finally putting an end to the War of 1812. However, official dispatches announcing the peace would not reach New Orleans until late February. On February 22, payment of the wharfage fee for the Enterprise was recorded.
On March 1, Shreve advertised in a Natchez newspaper that the Enterprise would "ply between Natchez and New Orleans every nine days until the first week in May" when the Enterprise would depart New Orleans for Louisville. On March 13, Andrew Jackson rescinded martial law. On April 21, payment of the wharfage fee for the Enterprise was recorded.
On May 1, John Livingston submitted a petition to the Federal Court accusing captain Henry Shreve and the shareholders of the Monongahela and Ohio Steam Boat Company of violating the territorial steamboat monopoly granted to Robert R. Livingston and Robert Fulton. John Livingston's petition requested a payment of $5,000 and the forfeiture of the Enterprise. 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.
On May 6, Shreve and the Enterprise finally departed New Orleans and, after a voyage of 1,500 miles, reached Louisville on May 31. The Enterprise was the first steamboat to reach Louisville from New Orleans. Then the Enterprise steamed to Pittsburgh and Brownsville. This voyage, a distance of 2,200 miles (3,500 km) from New Orleans, was performed against the powerful currents of the Mississippi, Ohio and Monongahela rivers. The importance of this voyage was expressed in newspapers throughout the West.
By August, the owners of the Monongahela and Ohio Steam Boat Co. had decided to expand their business by adding another larger steamboat to transport passengers and cargo between New Orleans and Louisville. To this end they planned to raise capital by selling additional shares at $500 each.
The Dispatch, owned as well as the Enterprise by the Monongahela and Ohio Steam Boat Company, steamed from Brownsville to the port of New Orleans by February 13, 1816 with important documents aboard for attorney Abner L. Duncan to use during the impending Enterprise trial. While docked at the levee, an incident occurred aboard the Dispatch that Robert Rogers, the first engineer, would record:
Accounts of this incident were published in newspapers throughout the West.
During May 1816, the Enterprise trial, judge Dominic A. Hall presiding, was held in the old Spanish courthouse, 919 Royal Street. The plaintiffs were represented by John R. Grymes, the defendants by Abner L. Duncan. First, Duncan submitted to the court Daniel French's 1809 federal patent for his improved steamboat engine, which powered the Enterprise. 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. On May 20, Judge Hall, stating that the Territorial Legislature had excedeed 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.
From the arrest and seizure of May 1, 1815, throughout the preliminary legal procedures, to the last testimony before Judge Hall during the Enterprise trial, Grymes and Duncan represented opposing positions. Out of court, however, they worked together as aides-de-camp for General Andrew Jackson during the recent siege of New Orleans and as conspirators engaged in profiteering from illegally seized Spanish property. Their accomplices included attorney Edward Livingston, Commodore Daniel Patterson, the smuggler Pierre Laffite, and the pirate Jean Laffite.
The seizures of the Enterprise and the Dispatch stimulated the Kentucky legislature to pass a resolution in January, 1817.
The Enterprise reached Shippingport on January 21, 1816. The Enterprise departed Shippingport, bound for New Orleans, on January 25, 1816. The Enterprise reached the port of New Orleans by February 27. The Enterprise reached the port of New Orleans by April 5. In 1817, the Enterprise reportedly sank at Rock Harbor, which was a popular anchorage below the Falls of the Ohio and near Shippingport.
The Enterprise demonstrated for the first time that steamboat commerce was practical on the Mississippi River and its tributaries. The Enterprise trial eliminated the ability of the monopolists to restrict competition. Furthermore, the Enterprise was relatively inexpensive to build, costing $9,000 compared to $38,000 for the New Orleans. These facts opened the way for the subsequent rapid growth of steamboat commerce on America's western rivers.