Thereafter, Hill did not seek elective office for a decade, although he continued to control the Democratic Party in Elmira's Chemung County, New York.  In the early 1880s, he reentered electoral politics, rising swiftly from Elmira alderman (1881) and mayor (1882) to lieutenant governor (1882), elected to the latter post on the Democratic ticket with Grover Cleveland.  In January 1885, Hill assumed the governorship when Cleveland resigned to become president.  Hill narrowly won his own race for governor that November, defeating Republican Ira Davenport by one percent.  In 1888, he was reelected by a slim margin of less than one-and-a-half percent over Republican Warner Miller.

During his gubernatorial administration (1885-1891), Hill opposed Republican efforts to enact civil service reform and liquor taxes, and he supported tenement house regulation and labor reforms, such as maximum work hours, abolishing prison labor contracts, and creating an arbitration board for labor disputes.  Through efficiency and attention to detail, Hill constructed a political machine that allowed him to dominate Democratic state politics into the early 1900s.  

In January 1891, Hill maneuvered to have the state legislature elect him to the U.S. Senate for a term commencing that March.  However, he did not take the seat until his gubernatorial term ended in January 1892, provoking critics to label him the "governor-senator."  When New York Republicans appeared to have won a majority in the state senate in November 1891, Hill orchestrated the invalidation of three Republican victories through Judge Maynard in order to retain Democratic control.  The judge is depicted in the cartoon's cesspool of corruption wearing a royal robe and emptying a ballot box.

After years of battling Cleveland for leadership of the New York Democrats, Hill unsuccessfully challenged the former president for the Democratic presidential nomination in 1892.  Hill's political machinations were too audacious for most Democrats in the rest of the country.  In the Senate, though, Hill usually defended the policies of the second Cleveland administration (1893-1897), as depicted on his wing in this cartoon.  

While Hill certainly desired to be president, he did not actively seek the gubernatorial nomination in 1894 (as the cartoon wrongly implies), although he did reluctantly accept it.  It was a year in which Democrats faired poorly, as the public reacted against an economic depression, and Hill lost badly that November to Republican Levi Morton, 53%-41%.  He never ran for office again, although he served out his term as U.S. senator (to 1897) and continued to exert influence, though waning, over the New York Democratic Party.  

Despite opposing the nomination of William Jennings Bryan and the free-silver plank in 1896 and 1900, Hill stood by his party rather than support the breakaway "Gold" Democrats.  At the 1900 Democratic National Convention, he lost the vice-presidential nomination to Adlai Stevenson.  Four years later, he managed the unsuccessful campaign of Alton B. Parker, the Democratic presidential nominee.  Thereafter, Hill concentrated on his law practice in Albany, New York, where he died in 1910.