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Ronald Reagan's rise to prominence was built on the conservative intellectual movement and the thinking of figures like Russel Kirk, Frederick Hayek, Frank Meyer, Irving Kristol,and William F. Buckley Jr. Reagan read these figures and built his sense of conservatism and political philosophy on their thinking. For example, Regan noted “As the prophet of American conservatism, Russell Kirk has taught, nurtured, and inspired a generation.” Reagan thought seriously about ideas like conservatism and libertarianism, saying:

If you analyze it I believe the very heart and soul of conservatism is libertarianism. I think conservatism is really a misnomer just as liberalism is a misnomer for the liberals -- if we were back in the days of the Revolution, so-called conservatives today would be the Liberals and the liberals would be the Tories. The basis of conservatism is a desire for less government interference or less centralized authority or more individual freedom and this is a pretty general description also of what libertarianism is.

Donald Trump's brand of populist nationalism has really changed the shape of the American right since he rose to power. In contrast to Reagan, I haven't been able to find many quotes from Trump talking about what being a conservative means beyond simple statements like:

"I really am a conservative, but I'm also a commonsense person. I'm a commonsense conservative," Trump said Tuesday. "We have to be commonsense conservatives, we have to be smart."

or:

“When you get down to it, I am a conservative person. I am by nature a somewhat conservative person,” he added. “I never looked at putting a label on myself, because frankly putting a label on myself, it didn’t matter — I wasn’t in politics … It was something that absolutely had no bearing on me.”

Now Trump is very much in Politics. I'm wondering how he describes himself in the ideological landscape and who his influences are. What does conservatism mean to Donald Trump, in his words?

Alternatively, Trump may have indicated that he doesn't think terms like conservative have real meaning and aren't particularly useful in his quest to make America great again. He might eschew previous political thinkers as old fashioned and unhelpful. If this is the case, speeches or quotes where he indicates these views would answer this question.

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    Donald Trump didn't run on a platform per se. More of an anti-platform: he ran on not being an elite, a member of the establishment, etc. etc. and he made sure to say enough things that the kind of person he was trying to contrast himself with would never say to ensure we knew he meant it. I'm still waiting for the meta game to come full circle and have a serious candidate run in 2020 on a platform of not being Donald Trump. Dec 21 '18 at 19:14
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    There's always the possibility that he doesn't know himself. This is very close to being closed as an "internal motivation" question, but I don't think it crosses that line.
    – Bobson
    Dec 21 '18 at 19:15
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    Lots of Trump supporters ONLY care about labels. Try telling them about a politician who wants to improve their healthcare coverage and raise their wages but happens to be labelled 'Liberal' and see what reaction you get. Dec 21 '18 at 21:35
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    @DJClayworth Lots of Trump haters ONLY care about labels. They oppose anything Trump does, even if Obama did the same.
    – Sjoerd
    Dec 22 '18 at 9:11
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    I'd take Reagan's libertarian position more seriously if he hadn't ramped up the war on drugs and condemned gay rights. It seems that his libertarianism only went as far as economics; on social policy he wanted to control other people just as much as the rest of the Republicans. Dec 30 '18 at 13:23
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The term 'conservative' refers to the idea that there are certain values within established, status quo society that need to be conserved: protected from change, degradation, or destruction. Liberalism is generally focused on the onward march of progress, the ways that society (ostensibly) can be changed for the better. Conservatism picks out elements of that change to oppose, on the grounds that they (ostensibly) are change for the worse. Under ideal circumstances this is a healthy dynamic, allowing forward movement without sacrificing the essential coherence of society.

In Reagan's era, conservatives were mainly concerned by progressive social and economic policies that were the result of liberal activism in the 60s and 70s: parity for women, gays, and minorities in the workplace, environmental and worker's safety regulations, the secularization and racial/gender integration of school systems and governance, etc. They focused on maintaining the traditional hegemony of white men in the workplace — which was viewed as the historical foundation of economic success in the US — and so promoted an ideal of small, laissez-faire governance that would not interfere with business practices as given.

Trumpism carries many of the same themes, but unlike Reaganism, Trumpism is a nationalist movement — drawn from elements of white ethnonationalism and Christian nationalism — fueled by four decades of resentment over the failure of conventional conservatism to stem progressive advances. Nationalism in this sense is a corruption of conservatism: where conservatism seeks to preserve what it perceives as good in society, nationalism only wants to destroy what it sees as bad; where conservatism tries to slow progress to a cautious pace, nationalism actively seeks to revert society to some mythologized 'perfect' era.

Trump himself is largely apolitical — the only side he ever seems to take is his own — and he does not exemplify any of the traditional conservative virtues (moral rigor, generosity, hard work, honesty, self-discipline, and the like). But Trump has managed to capitalize on the grievances and violent ideation of the most resentful elements of US conservatism.

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This is an interesting topic to me, but it seems that Reagan was likely our last real philosophical President. Trump has often been criticized for lacking an ideological center. Perhaps he doesn't really know where he falls on the spectrum, so he just choses not to speak about it? The best we can really do is look at his actions. I would classify his recent move to reduce troops in war zones as more of a 'libertarian' move, but it's hard to judge his motives at this time. He does a lot of stuff that doesn't fall into the realm of what typical Republicans would do. This is why the establishment hates him. I remember him saying "that the Constitution, doesn't apply to all things", which tells me that in the broad scheme of things, he's not very 'libertarian'. I would love to see someone neutral person, outside the MSM interview him on this topic. In fact an unprepared interview conducted by Ron Paul would be excellent to see.

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    "This is why the establishment hates him". Which establishment did you have in mind? Dec 30 '18 at 13:33
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    The Republican/Democrat duopoly
    – Aporter
    Dec 30 '18 at 14:49

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