We were so close. So very, very close. I’m sure you all remember when, back in August, the New York Times asked if the “Libertarian Moment” was finally upon us, and whether the “genuine political momentum” behind the libertarian movement would carry its Pearl Jam-like poster boy, Sen. Rand Paul, all the way to the Oval Office. After spending their political lifetime at the margins, the small-government libertarians were finally set to make a big push to get one of their own in the White House. It was all happening!

But then Alison Lundergan Grimes (remember her?) stepped in and tried to ruin all the fun:

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Six weeks after she lost her own bid for the U.S. Senate, Secretary of State Alison Lundergan Grimes (D-Kentucky) tells WHAS11 if U.S. Sen. Rand Paul (R-Kentucky) tries to appear on the same ballot for both Senate and President in 2016, she will challenge him in court. "The law is clear," Grimes said. "You can't be on the ballot twice for two offices."

The problem for Paul, as you probably gleaned from the article excerpt, is that he has ambitions to run for the presidency in 2016, but is also up for reelection to the Senate in 2016, and Kentucky law won’t let him do both. Grimes, in her capacity as Kentucky’s top election official, is of course duly bound to uphold the law and fully justified in seeing that it is followed to the letter – though Rand’s horribly tortured campaign-trail limerick about how Grimes sold her soul to Hollywood liberals probably made her decision a bit easier.

Paul has been aware of this problem for some time and had hoped that the 2014 elections would render it moot – if Republicans had taken control of the Kentucky legislature, they would have rewritten the law especially for him. But the Democrats held on to the House in the state, which guarantees the law will stay on the books as is.

What does this mean for Rand? Well, first things first – he and his advisors had to get in a few cheap digs at Grimes for old time’s sake. “Good to see her still fighting after such a huge loss,” Paul aide Doug Stafford told the Lexington Herald-Leader. “Maybe since she is talking again she can finally say whether or not she voted for President Obama.” Cutting and relevant though they may be, remarks like these do little to resolve the matter at hand.

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So what is he going to do? Well, like any good “Rule of Law” libertarian, Rand Paul is investigating every single way possible to circumvent the statute so that he can do what he wants when he wants and face no consequences for embarking on his chosen path.

The National Journal’s Shane Goldmacher wrote an excellent rundown of Team Paul’s “exhaustive political and legal battle plan to ensure he can run for both Senate reelection and the White House in 2016.” Basically, Paul wants to find a way to rearrange the machinery of government entirely for his own benefit, whether it be through the political parties or the courts. Their “top” option is to ask the Kentucky Republican Party to forgo a primary election and hold a caucus instead, which would allow Rand to get around the law on a technicality since his name won’t appear on an actual ballot. Of course, that requires approval from the party (which would also have to put up the funding) and it only solves half of the problem – he still has to appear on the ballot in the general election.

Another option is to file a lawsuit claiming the law places an unconstitutional burden on Rand Paul’s right to run for all the political offices he wants to. My colleague Jim Newell observed, correctly, that this option would provide for fantastic entertainment, as it’s tailor-made for the “dorm-room philosophical bloviation that Rand Paul’s known for.” The problems for Rand are that there’s no guarantee this will work, and he risks looking a bit petulant for filing a lawsuit because he can’t have everything he wants all at once.

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And that raises the obvious question: why can’t he just wait? Rand could coast to reelection in 2016 and then run for president in 2020 or 2024 without issue. The answer brings us back to the “Libertarian Moment.” Rand Paul has to know that his best shot at this is now. He’s got the insurgent libertarian movement behind him and a “big-government socialist” in the White House to run against. His party’s base is dissatisfied with the GOP establishment and might be open to someone slightly unorthodox. There’s no guarantee these conditions will last.

None of this is to say that he would win, of course. Rand’s yen for conspiracy theories and serial flip-flopping on just about every issue make him an exceptionally flawed candidate. But at least he has sense enough to know when the timing is right.