Don't let the subtitle fool you: we're talking about President Grover Cleveland, not the adorable monster on Sesame Street. They do share a few things in common, but for now we're going to stick to the Grover who wasn't blue.
As one of nine children of a Presbyterian minister, the future POTUS had to forgo college to help support the family. He clerked for a family friend who was a lawyer and took to it like a golden retriever takes to rolling in mud puddles. He passed the bar and went to work, and he quickly developed quite the reputation for being a morally upstanding young man.
Fun fact: Cleveland didn't fight in the Civil War. He paid an immigrant from Poland to take his place (source). The things you can get away with and still be president—sheesh.
In 1871, there was a new sheriff in town in Erie County, NY. It was the first office Cleveland held. Although he made an astonishingly rapid accession into the upper tiers of American government, he wasn't really a go-getter by nature. Rather than put his name forward and stubbornly trudge through political campaigns, most of his successes came from nominations by friends and by being in the right place at the right time, with the right views on various political issues.
A bipartisan group of citizens approached Cleveland in the early 1880s offering to support him as the next Mayor of Buffalo, at the time one of the most corrupt cities in the country. His reputation as an honest fellow who worked against the political machine made it an easy win (source). Getting rid of the kickbacks and general corruption in the city government made an impression on all those fine New Yorkers, and when he ran for governor as a reformer, he won again.
The people loved Cleveland for standing up to Tammany Hall, the political machine that ran New York City politics with an iron fist. The Democratic party (and even reformist Republicans like Teddy Roosevelt) took note of this activist, graft-busting governor. At a time when the U.S. government was facing accusations of being rife with immorality and depravity, they needed an honest man as a presidential candidate. The Democrats chose Cleveland.
But guess what? They had oppo research even in 1884.
A newspaper in Buffalo dug up a story that Cleveland was the father of a child as a result of an affair with a certain Maria Halpin ten years prior. She wasn't the most monogamous woman on the planet, so Cleveland said he couldn't be sure that he was the boy's father. But the story is that he claimed paternity because he was the only bachelor among Halpin's gentleman friends, and he didn't want to have his married pals humiliated by the publicity. Nice guy that he was, he found a compassionate foster family for the boy and offered financial support (source).
Of course, every story has two sides at least, and Maria Halpin had hers: Cleveland had forced himself upon her, and when she became pregnant, paid her off to give up her son and got her committed to a mental hospital (source).
In a story we're all too familiar with, these allegations of sexual misconduct didn't keep Cleveland out of the White House. Voters thought his opponent, James Blaine, was even more corrupt. The Republican campaign slogan of "Ma, Ma, where's my Pa?" had its Democratic response: "Gone to the White House, ha ha ha" (source)!
President Cleveland saw the Native Americans as "wards of the state," saying in his first inaugural address that "[t]his guardianship involves, on our part, efforts for the improvement of their condition and enforcement of their rights" (source).
As a reformer, Cleveland thought that the Dawes Act would be a step forward from the reservation system that had resulted in so much poverty and suffering for the tribes. He signed the Act into law and the rest is (tragic) history.
Cleveland was less sympathetic to the enforcement of the rights of African Americans that had been guaranteed in the 14th and 15th Amendments. He thought the whole Reconstruction business was a disaster and he didn't enforce the voting rights of Black Americans with any enthusiasm.
In the 1888 election, Cleveland won the popular vote but lost the Electoral College, and therefore the presidency, to Benjamin Harrison because of the unpopularity of his stance on lowering tariffs, which hurt the industrial states and lost him even the support of New York voters. He went back to lawyering for four years and ran again in 1892.
This time, Tammany Hall supported him, and Cleveland became the only president to serve two non-consecutive terms in office.
He may have wished he'd lost.
In 1893, the nation was hit by a financial panic, cleverly called the Panic of 1893, that involved railroad bankruptcies, bank, failures, striking miners, a tanking stock market, and 19% unemployment (source).
Cleveland had had it. He refused to run for a third term (no term limits then), and retired to Princeton, NJ, where he died in 1908.
His views on Native Americans was consistent with his views on African Americans and women: he didn't support equal rights for any of them, and even opposed the vote for women. Cleveland's last words were ""I have tried so hard to do right" (source).
Maybe "right" meant something different in those days.