Dryden was involved in a number of scandals during his time in office. In 1897, he appointed his brother George W. Dryden as the Registrar of Ontario County, causing dissension among fellow Liberals also interested in the job. The Conservatives also charged that Dryden had promised the position to several people in return for monetary compensation, and Dryden sued Conservative candidate William Smith for damages. Smith was unable to prove the allegations and was forced to withdraw the charges. Politically damaged, Dryden lost his seat in the 1898 Election. However, he refused to resign, challenged opponent Charles Calder in the courts and won the resulting by-election. Calder protested, necessitating another by-election, with Dryden emerging again as the victor. Rumours to the effect that Dryden bribed Calder to withdraw his protest persisted and hurt him politically. He was re-elected again in the 1902 Election but lost his seat in 1905.