In 1999, Gershon ruled that New York City mayor Rudolph Giuliani could not cut the Brooklyn Museum of Art's funding after it mounted an exhibit entitled "Sensation". Giuliani described the works in the exhibit as "sick" and "disgusting." 
In 2000, Gershon ruled that New York's century-old kosher food laws violated the First Amendment.
In the spring of 2006, Gershon presided over the trial of Shahawar Matin Siraj, a Pakistani immigrant who was accused of plotting to blow up New York's Herald Square subway station. After a four-week trial, a jury found Siraj guilty of four crimes, including plotting to bomb a public transportation system. On January 8, 2007, Gershon sentenced Siraj to 30 years imprisonment for his role in the plot.