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Ryder was founded in Miami, Florida, in 1933 by James Ryder as a concrete hauling company with one truck, a 1931 Model "A" Ford. In 1938, Ryder signed a five-truck lease deal with Champagne Velvet Beer, increasing Ryder's fleet to 20 trucks. By the following year, the fleet had more than 50 trucks. This led to Ryder changing its focus from distribution to leasing.
Ryder bought Great Southern Trucking Company in 1952. In 1955, Ryder System, Inc. was formed to combine Great Southern and Ryder Truck Rental. Ryder System went public in 1955. In the 1960s and 1970s, Ryder expanded into distribution and supply chain. James Ryder retired in 1978.
Ryder trucks rented by terrorists and filled with explosives were used as weapons in both the 1993 World Trade Center bombing and the 1995 Oklahoma City bombing, as well as vehicle-ramming attacks such as the 2018 Toronto van attack.
In 1996, Ryder decided to focus on commercial truck rental and leasing, and exited the "one-way" consumer truck rental business; which was purchased by equity firm Questor Partners Fund LP, who later sold it to Budget Truck Rental in June 1998.
In December 2011, the non-partisan organization Public Campaign criticized Ryder for spending $960,000 on lobbying and not paying any taxes during 2008 to 2010, instead getting $46 million in tax rebates, despite making a profit of $627 million.
In 2017 Ryder launched electric truck rentals in California, and Chicago, Illinois. The trucks were equipped with 70 kWh batteries, which had an estimated range of 100 miles. Ryder is the exclusive maintenance provider for Workhorse 's electric fleet in North America, first launched in the San Francisco Bay area in 2018.