Okay, history question here: What, if any, legacy for liberty did Grover Cleveland leave? Does it help the cause of liberty, long-term, to elect good presidents?
In my opinion even grover cleveland was a statist. For instance, he helped annex hawaii and provided subsidies to big business. His election as a laissez-faire liberal had no effect on US imperialism which rocketed into prominence just after his term and it really wasn’t until the excesses of wilson did people actually think back with longing to the days of less regulation. The same could be said of federalism and it’s excesses in the early 19th century which encouraged the people to vote for small government republicans. So if anything it is the failures of collectivism which inspires people to elect (actually or not) free-trade presidents and not free-trade presidents which inspire the people.
Grover Cleveland actually did not let the US government annex Hawaii during his presidency.
Is this Cleveland’s fault, or the fault of his sucessors - I say its, without a doubt, the latter.
In my humbe opinion, Grover Cleveland was most likely the most ibertarian president other than Jefferson. Amongst his accomplishments include him loosening the grip the spoils system had upon the American bureaucracy, reducing tariffs, his refusal to meddle with the gold standard, and his opposition to imperialism, and expansionism abroad.
May as well look at the end of Cleveland’s presidency as the death of classical liberalism. Sure, after he left office there was some last hurrahs from classical liberals such as the Palmer/Buckner (Gold Democrats) ticket in 1896 and the Alton Parker run in 1904. But they never were able to gain power again or hold back the state. It was a good fight for over 100 years but the Democrats devolved into populism and eventually social democracy.