It's a fact that drives liberals crazy, and has become a preoccupation for President Donald Trump: Hillary Clinton, the Democrats' choice, crushed Trump at the ballot box, winning the popular vote by a margin of roughly 3 million, but Trump cruised to a win in the Electoral College, sweeping up 304 of 538 votes.

It was the second time in recent history that the winning presidential candidate, a Republican, took office even though more people voted for the Democrat. It's also a system Harvard law professor Lawrence Lessig believes is a Constitutional offense – and practically guarantees another popular-vote loser will again become commander-in-chief in the very near future.

Every four years, the presidential election "focuses on 14 [swing] states, to the total exclusion of the rest of the country," says Lessig, who ran an under-the-radar campaign for president as an independent in 2016. "Those 14 states are not representative of America. They're older, whiter and their industries" like mining and farming "are representative of 19th-century industries."

That's why his organization, Equal Citizens, launched a project called Equal Votes to sue in four states last week, arguing that the winner-take-all electoral-college system violates the Constitution's equal-protection clause and undermines the democratic principle of fair representation.

Backed by a powerhouse legal team – including David Boies, who fought for gay marriage in California and represented Vice President Al Gore before the Supreme Court during the disputed 2000 presidential election – Lessig's quixotic campaign is aimed straight at the high court: He wants the justices to declare the current system unconstitutional, a ruling he believes will lead to the popular election of presidents and break the parties' hammerlock on power in so-called red states and blue states.

"This is not an attack on the Electoral College," he says. "It's an attack on how the state grants the electors."

Boies took it a step further: "Under the winner-take-all system, U.S. citizens have been denied their constitutional right to an equal vote in presidential elections," he told Bloomberg News. "This is a clear violation of the principle of one person, one vote."

There are just two states that apportion its delegates: Maine and Nebraska, small-population states with a total of nine delegates between them. Under the system, the presidential candidates get one delegate for each congressional district he or she wins (three districts in Nebraska, two in Maine), and the candidate that wins the statewide vote gets the rest.

The legal team led by Boies filed lawsuits late last week in Texas and South Carolina, two Republican strongholds, and Massachusetts and California, states where Democrats are in control; together, the states account for 113 of the total 538 electors in the U.S.

"A Republican in California, no less than a Democrat in Texas, voting for the President of the United States should have her vote for President counted equally, regardless of whether she happens to vote with the majority in her state," Lessig wrote in a Medium post announcing the lawsuits. "Yet under the system as it is now, their votes are counted unequally. If they vote with the majority, their vote matters. If they vote with the minority, their vote counts for zero."

Changing that entrenched dynamic, however, is a pretty heavy lift, according to analysts.

"Similar cases in the past in several states have not won," Ballotpedia, an elections website, wrote in a succinct post about Lessig's lawsuits. It then lists roughly a half-dozen similar cases, filed between 1966 and 1981, in Southern states from Louisiana to Virginia; they all made similar arguments as Lessig's, and they all failed.

Ballotpedia also drily noted a 1966 lawsuit in which 13 states sued the other 37 over electoral-vote distribution: "That case was filed directly in the U.S. Supreme Court, but that Court refused to hear it."

Derek T. Muller, a Pepperdine University law professor and author of the Excess of Democracy blog, doubts that Trump's election – which exposed the same flaws, more or less, that led to the historic, rancorous Bush-Gore election in 2000 – probably hasn't moved the needle towards ditching the electoral-college system.

"Since Election Day, a number of litigants – admittedly, mostly (if not all!) pro se – have attempted to file just such challenges," Muller wrote in a blog post, using legal jargon for a litigant acting as his or her own attorney. "They've lost every time (0-6 by my count)."

However, it doesn't mean Lessig's gambit is worthless, Muller wrote.

"Of course, part of litigation like this is theatrical," he said. "Another part of litigation like this is to get the Supreme Court to address the merits of the dispute, even if lower courts ought [to], under existing precedent, summarily dismiss such claims. But, time will tell whether this effort is any more successful than the many, many failed efforts that have gone before."

Lessig acknowledges that, like his independent bid for president in 2016, success is a longshot, mostly because the two major political parties don't have much of an incentive for change. "The politics are incredibly difficult," he says.

Nevertheless, the present moment – a president with historically-low approval ratings, bitter fights over hyper-partisan gerrymandered districts, evidence Russia meddled in the last election, warnings their hackers will try again if nothing's done – makes Lessing's quest to overturn the electoral-college system more urgent than previous lawsuits.

"You couldn't design a better system for Russian hacking," Lessig says. "It makes it much much, easier to target and flip an election" when just a handful of states decide the outcome; that logic, he says is a key reason he believes the Supreme Court will be "eager" to grapple with the issue.

At the same time, Lessig says, "it's pretty clear that going forward," unless the electoral system changes, the U.S. will probably get another president who takes office with a plurality of the popular vote – or less. Though Republicans have benefitted, he says, it's only a matter of time until the shoe is on the other foot and Republicans must deal with a "minority president."

For that reason, "It was important that we frame this in a way that people see it affects both Democrats and Republicans," says Lessig. If you're a Republican in Massachusetts, or a Democrat in South Carolina, he says, the system "counts your vote but throws it away."

And the time to change the system is before the next crisis presents itself, like in the 2000 presidential election – a dispute in uncharted political territory, which analysts say helped accelerate the acrimonious red state, blue-state divide.

"This is a hard constitutional question to answer. We don't think it's easy" on any side of the issue, Lessig says. "But we should resolve it as quickly as possible. That's the only time these questions get raised: In an election year, or after something like Bush v. Gore."