President Roosevelt issued the most executive orders, according to records at the National Archives. He issued 3,728 orders between 1933 and 1945, as the country dealt with the Great Depression and World War II.President Truman issued a robust 896 executive orders over almost eight years in office.President Obama has issued 184 orders so far in his presidency. His predecessor, President George W. Bush, issued 291 orders over eight years, while President Bill Clinton had 364 executive orders during his two terms in office.resident Truman issued a robust 896 executive orders over almost eight years in office. President Obama has issued 184 orders so far in his presidency. His predecessor, President George W. Bush, issued 291 orders over eight years, while President Bill Clinton had 364 executive orders during his two terms in office.