[2] After being sold back to Crosby by the lottery winner, A.H. Lee, the hall began producing more consistent performances.

In 1989 the city demolished the deteriorated properties on the site where it once stood, and took decades to subsequently formalize plans for redevelopment of the so-called Block 37.

[1][3] During the city's twenty-year discussion regarding what to do with the property, it was used as an art studio for Chicago public school students and as a skating rink through the winter season.

The area's only theater, built by John Blake Rice in 1847, had been destroyed in a fire shortly before Crosby's arrival.

James Hubert McVicker, a close friend of Crosby's who was a neighbor in the Briggs House hotel, built a playhouse.

McVicker's Theater became the cultural center of Chicago entertainment, but Crosby believed that the city was overdue for a grand opera house like the ones he knew back East.

The first floor housed businesses like music publishers Root & Cady, the piano store of W.W. Kimball, and the restaurant of H.M. Kinsley.

The conductor Jules Grau would lead the inaugural series of Italian operas, performed by a company from New York City's Academy of Music featuring Clara Louise Kellogg.

Il trovatore was the first performance, followed by a four-week season with Lucia di Lammermoor, Il Poliuto, Martha, Norma, Faust, Linda di Chamounix, La sonnambula, I puritani, Un ballo in maschera, Dom Sébastien, Lucrezia Borgia, Ernani, and Fra Diavolo.

The Crosby Opera House Art Association was formed and they organized a scheme to raise funds and dispose of property through a lottery.

[7] The prizes, and their values advertised, were:[10] The drawing was originally scheduled for October 11, 1866, but because of high ticket demand it was delayed until January 21, 1867.

Nineteen trusted public officials from around the country such as banker William F. Coolbaugh, former Lieutenant Governor of Illinois Francis Hoffmann, American Express agent J. C. Fargo, and historian David Pulsifer oversaw the drawing.

Crosby maintained possession of The Yo Semite Valley, An American Autumn, and a sculpture of Abraham Lincoln by Leonard Volk, valued at $2,500.

Subtracting the $200,000 given to A.H. Lee, Crosby paid off the construction cost and pocketed profits all while still maintaining ownership of the opera house.

Works included Médée, Adriana Lecouvreur, Marie Stuart, Deborah, Love and Intrigue, and Emilia Galotti.

Starting on December 28 and continuing for over a month, notorious businessman James Fisk leased the house for his production, The Twelve Temptations.

Lorenzo Sabine's refusal to accept the remains of actor George Holland, a charity event was held on February 16, 1871, at Crosby's, raising almost $2,000 in support of Rev.

Theodore Thomas was on tour in early October 1871 and had planned to head to the opera house for a two-week series event of orchestral concerts for the reopening.

By the evening of the next day, the Great Chicago Fire had destroyed over 3.3 square miles (8.5 km2) of the city, including Crosby's Opera House.

[12] Chief usher James S. Osgood and Crosby went back to the opera house to save some of the art gallery.

They took large pictures out of the frames and lowered them by rope out of the windows, eventually taking them to Garrisons House at 226 South Wabash Street.