Cleveland left a mixed legacy and is not considered one of the country's great leaders. His actions, however, solidified the Deep South around the Democratic Party, largely because he signaled to white Southerners that he was a racist. While dishonorable, his actions provided a strong voting base the Democrats could count on during much of the 20th century (until Johnson). The implications, however, were the continuation of Jim Crow laws and segregation among other racist policies in the South.
Cleveland strengthened the executive branch of the government through the heavy use of vetoes and his refusal to allow Congress to see documents held by the executive branch. He also used his authority as president to singlehandedly deploy federal troops to break up the Pullman strike and to send United States naval vessels to Panama. This use of executive privilege is perhaps his most lasting legacy: he is credited with paving the way for presidents like Franklin Roosevelt who would act independently of Congress.
It is also worth noting that Cleveland is the only president to win an election, then lose an election, then come back to win an election. He is, in other words, the only president to serve two non-consecutive terms.
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