After winning the Republican primary to be the party's Kentucky Senate candidate, a series of interviews - one with NPR and another with the Rachel Maddow Show - left Rand Paul in a bit of trouble. The issue concerned his views on a section of the Civil Rights Act of 1964. In summation, his views are that the federal government does not have the constitutional right in legislating who a private business may or may not choose as patrons - if the business owner decides to refuse service to a person of another race, it was within his right as the property owner to do so. This is in keeping with the libertarian view that a key function of government is to protect the rights of property owners and the right to free speech of its citizenry.

In theory, the community at large (leveraging their collective might as consumers) could boycott the discriminatory business owners and hurt him economically as a protest against his opinions. In the libertarian viewpoint, this is a self-correcting mechanism that does not require governmental involvement and zero infringement on the property rights or freedom of speech of anyone person...in theory, at least.

The problem with Paul's (and libertarians') view on this issue is that it makes several assumptions:

Government is an entity separate from the wider society that has a set (if arbitrary) role in protecting "natural rights" - rights that include the protection of private property and free speech but not freedom from unjustifiable discrimination or injustice; essentially, government has no right to protect the welfare of a minority group due to an arbitrary demarcation of responsibility and duties libertarians adhere do.
The notion the wider society would actually be opposed to the discriminatory actions of the hypothetical business owner and be bothered to actually boycott the hypothetical business. For example, we all know that many goods on sale at your local discount store are made in sweatshops that abuse the rights of their workers - how are the boycotts against these sweatshops and Wal-Mart working out? They're still in business (and thriving) despite years of knowledge of these practices.
The notion that property rights are more important than the right of a citizen from being discriminated against.

While these views may seem reasonable to Paul and his ilk, these ideological views are completely out of touch from reality. It is easy to say that people will unite and protest against unfair business practices if these practices are known in the open; but when the situation emerges, how many people will actually partake in the boycott? And what is to be done when nearly every business in the hypothetical community are also discriminatory as well? Who will protect the minority group from this?

It is easy for an idealistic libertarian to tout how, if given the chance, he would march along side Martin Luther King Jr. and the Civil Rights movement in condemning racism...only after the fight for equal rights has been mostly won already. An idealistic libertarian does not have the burden in having an internal debate over the rampant racism and discrimination against blacks and other minority groups pervasive throughout the entire country and the rights of business owners in choosing whether or not to discriminate. When faced with a situation that causes this type of conflict between one's ideals and one's common sense, it is always troubling. Fortunately for most libertarians, they do not have to face history in their day to day lives.

Unfortunately for Rand Paul, he now needs to balance his idealism and reality. It will be interesting to see how he proceeds from here.