Palazzo Drago Airoldi di Santa Colomba may be considered for its position and development among the most interesting historical Sicilian residences of the Cassaro, the current Via Vittorio Emanuele. The building, which stands on existing Arab and Roman foundations, is located at the corner of the San Giuseppe D’Arimatea alley, in the Palazzo Reale district. Via Vittorio Emanuele corresponds to the ancient Cassaro, the main road axis of Palermo from the time of the Phoenician foundation of the city, and the fundamental cornerstone of all the city streets until the opening of Via Maqueda.

The Cassaro continues to be the privileged site of the aristocratic settlement in the Baroque period because it represents the link between the center of temporal power, the Royal Palace, and that of religious power, the Cathedral.

For the inhabitants of Palermo, this street has always been the center of all public activities. The Cassaro was the central axis of the Phoenician and Roman city, and was further transformed during the 16th century. Initially, the pre-existing road was modified by making it longer and wider, with an aim of modernization and embellishment. For those who walked the Cassaro from the highest point towards the sea, the Palace, the Largo Aragona, the Piazza Pretoria and the Marina square appeared on the right; on the left the Cathedral and, just protected by a side scene of houses, the Cala.

Palazzo Drago is located in the upper section of the Cassaro, between the Quattro Canti and the Royal Palace, the most prestigious section of the entire street, corresponding to the ancient Neapolis, where many of the most important palaces of Palermo stand. The location on the street axis must have been a conditioning factor for the architectural definition of the building, capable of setting itself in a highly qualified context.

The exact date of construction of the building is unknown, as well as the name of the author or of the family who commissioned the baseline structure and the current complete morphology of the building: in fact, innumerable buildings have existed in the same location since the age of the Phoenician. 

In 1714 the building is safely owned by Casimiro Drago, president of the Consistory. The coat of arms on the portal unquestionably witnesses the belonging of the building to the Drago family. A further proof of the ownership of the building is also a famous engraving by Francesco Cichè, depicting the main facade of the building and the magnificent late Baroque portal surmounted by a mixtilinear tympanum, filled with volutes, with an emblem depicting a dragon.

When the Palace became the property of Biagio Il Drago, son of Casimiro I, some changes were made to embellish and qualify the building both architecturally, with the renovation of the courtyard terrace in 1744, and decoratively, with the frescoes in the main hall performed in 1745 by Olivio Sozzi, a figure of absolute importance in the Sicilian painting scene of the eighteenth century, and others in the adjoining room. In the nineteenth century, when the building passed ducally to the Airoldi family, marquises of Santa Colomba, substantial changes were made to the external facade on Via Vittorio Emanuele and to the internal court. 

Among the most illustrious personalities of the family it is worth mentioning Gian Battista Airoldi, Duke of Cruillas, Praetor of the city of Palermo in 1808, whose marble bust may be seen along the access stairs to the noble floor.

The restoration project of the façade of the building on Corso Vittorio Emanuele as well as the inner courtyard, dated 1872, are by Giovanni Battista Filippo Basile, who distorts the original baroque character of the building to intone to the eclectic-classical taste of that time. The neo-sixteenth and neo-Pompeian features of the frescoes in the salons overlooking Corso Vittorio Emanuele suggest  that they were performed similarly to the restoration of the facades; conversely, the pergola in wrought iron outside the noble floor displays an art nouveau appearence.