Spanning nearly three miles, the Gandy is one of three bridges connecting Hillsborough and Pinellas counties (the other two are the Howard Frankland Bridge and the Courtney Campbell Causeway). In 1910, H. Walter Fuller partnered with George S. Gandy, Sr. to construct a bridge over Upper Tampa Bay. When WWI began, Fuller was required to submit his plans for approval by the War Industries Board, who reviewed all infrastructure projects exceeding $250,000. When the Board effectively canceled the bridge construction by refusing financial support, George Gandy bought out Fuller's interests and proceeded alone. The bridge formally opened in November of 1924. Drivers paid a toll to cross the bridge Until it was seized by Franklin D. Roosevelt's administration in 1944. By the mid 1950s, some believed that the bridge was outdated and dangerous for travel. A second Gandy was built in 1956 and used for vehicular traffic until 1997, when the Florida Department of Transportation sought to demolish it. Residents lobbied to keep the bridge for pedestrians and cyclists, after which it became known as the Friendship Trail Bridge. When an inspection team discovered significant structural deficiencies, the Friendship Trail Bridge was closed in 2008. In 1996, a fourth version of the Gandy Bridge was constructed that remains open to vehicular traffic today. It carries U.S. Highway 92/Interstate 275. Driving across the Gandy affords a splendid view of Old Tampa Bay.
Florida postcards from Hillsborough Country trace the bridge's transformation over time, beginning with the first version. Many 1920s and 1930s-era cards boast about the bridge's status as the longest in the world. Others capture the toll booths and the Friendship Trail Bridge. More recent postcards present the Gandy as seen from above in full color, much like a contemporary photograph.