[2] Originally, Shady Side was owned by the Morrisania Steamboat Company, and ran passengers to upper Manhattan and the Bronx by way of the East River.

Captain Longstreet, superintendent of the Morrisania line, took control of Shady Side in response one morning in April 1875 and swung her around in such a way as to knock the beam off Sylvan Dell.

[7][8] In 1881, it was reported in The New York Times that the police intended to buy her for the 24th precinct, and that "she cost $83,000, was sold to the steam-boat company for $58,000, and the amount now ask [sic] for her is $38,000.

The case went to the New York Supreme Court, which ruled against the boat's operators and enjoined them from running that route, an injunction that was re-ratified in July.

The two firms that ran the Chrysteneh, the Riverdale and the Caroline A. Peene began blocking docks that the Shady Side wanted to use and casting away her lines.

In the first incident, in mid-March 1875, Shady Side struck and sank a tug boat called Mary, which was backing out of a slip between piers on the East River near Corlears Hook.

George F. Townsend sued as a result and was awarded damages in May of the next year, Judge Blatchford finding that the tug was blameless and not outside the end of Jackson Street pier, whereas Shady Side was moving too fast given the fog.

Shady Side was abandoned on the mud flats at Fort Lee, New Jersey in 1922 when the Black Star Line collapsed as its owners were convicted of mail fraud.