On Feb. 11, Future Tense—a partnership of Slate, the New America Foundation, and Arizona State University—will host an event on cryptocurrencies at the New America office in Washington, D.C. For more information and to watch the webcast, visit the New America website.

Charlie Shrem was an early adopter of bitcoin, a decentralized peer-to-peer virtual currency built around cryptography. By 2011 he co-founded BitInstant, a service through which users could exchange government-backed currency to bitcoin and vice versa. Considered “one of the big faces of bitcoin,” Shrem naturally became the vice president of the Bitcoin Foundation, the nonprofit organization that “standardizes, protects, and promotes the use of Bitcoin.”

Charlie Shrem was arrested on Jan. 26, but the wheels had already begun to turn on Jan. 24, when a sealed criminal complaint was filed in United States of America v. Robert M. Faiella, a/k/a “BTCKing,” and Charlie Shrem. The criminal complaint is centered around “BTCKing’s” activities on the Silk Road, a Tor-hidden online marketplace for drugs and other illicit goods that was shut down last year. Shrem, who allegedly helped BTCKing launder drug money, is no kingpin, not even if you take the government at its word. Yet the Department of Justice was oddly smug in its press release, taking pains to include the phrase “Ceo of Bitcoin Exchange Company” in the title. This arrest wasn’t just about drugs. By arresting a vice president of the Bitcoin Foundation, the Department of Justice was firing a warning shot for the entire bitcoin community.

The criminal complaint in U.S. v. Ulbricht (otherwise known as the Dread Pirate Roberts case) had included this curious line: “Bitcoins are not illegal in and of themselves and have known legitimate uses.” That line—indeed, most of the description of bitcoin—is repeated in the Shrem complaint. At the time of Ulbricht’s arrest, it could have been understood as a sign that the government recognized that bitcoin’s Wild West days were over. After all, many of the exchanges had assented to regulation by the Financial Crimes Enforcement Network (a federal agency under the Department of the Treasury), thus launching the currency into mainstream respectability.

Now it seems that the government has merely shifted its focus. It is no longer concerned about whether bitcoin in itself is illegal: It is concerned with its capacity for anonymous, hidden payments. In other words, money laundering, as defined by 18 U.S.C. 1956—a charge levied in both the Shrem and Ulbricht cases. It was also used to charge defendants in the Liberty Reserve case (which I’ll describe further down), a case that might be a blueprint for things to come.

Transactional freedom is not synonymous with money laundering, no more than bitcoin should be synonymous with anonymity. (In fact, the open-ledger design of bitcoin doesn’t guarantee privacy. In response to such concerns, innovations like Matthew Green’s Zerocoin and Cody Wilson and Amir Taaki’s Dark Wallet have focused on preserving users’ privacy.) As the U.S. government ramps up its focus on money laundering through digital means, it is worth piercing through the concept of what money laundering actually is, and re-examining why we should care about anonymous payments.

In the wake of the diplomatic cables leak in 2010, members of the United States government convinced MasterCard, Visa, PayPal, and other payment processors to voluntarily block donations to WikiLeaks. Bitcoin had barely celebrated its one-year anniversary, but many early adopters had already spotted the potential to fund WikiLeaks through the decentralized, borderless currency. But bitcoin’s pseudonymous founder, Satoshi Nakamoto, vehemently opposed this use of bitcoin, because he was concerned that WikiLeaks controversy would rebound disastrously on bitcoin. WikiLeaks refrained from accepting bitcoin donations until Satoshi Nakamoto “disappeared” in the spring of 2011. Today WikiLeaks reports that the majority of its funding comes from bitcoin and other cryptocurrencies, even though the financial blockade has since partially lifted.

Cryptocurrency is an appealing choice for prospective WikiLeaks donors. Not only does it bypass the fees, restrictions, and potential seizures that third parties might impose on these transactions; it can also help obscure the donor’s connection to an organization that her own government may be hostile toward. Of course, anonymity has never been a prominent design feature of bitcoin, but mixing services allow users to anonymize payments, and therefore offer possibilities for individuals to materially support unpopular causes without fear of government reprisal.

But these same possibilities can also enable tax evasion, the laundering of drug money, and political corruption. For some, this particular capability is reason enough to call it “evil.” Author Charles Stross writes:

BitCoin looks like it was designed as a weapon intended to damage central banking and money issuing banks, with a Libertarian political agenda in mind—to damage [states’] ability to collect tax and monitor their citizens financial transactions.

But even beyond some nefarious “libertarian agenda,” anonymity in payments has serious repercussions for democracy. Cryptocurrency can be used to bypass campaign contribution limits: Shunting money from a corporation to a political action committee requires some paperwork and a lawyer, while donating money to a candidate who accepts bitcoin requires only a laptop and an Internet connection. If corruption in politics seems to be a problem now, then anonymous payments through cryptocurrency—like digital briefcases full of nonconsecutive bills—are potentially a disaster.

Regardless, it’s important to recognize that anonymity as free speech is not just an empty hypothetical—it’s part of the American legal tradition. In 1956 the Alabama attorney general sued the NAACP for allegedly failing to comply with a statute that required corporations to register with the state. The attorney general claimed that the NAACP had caused “irreparable injury” to the citizens and residents of the state, because it had, among other things, “given financial support and furnished legal assistance to Negro students seeking admission to the state university; and had supported a Negro boycott of the bus lines in Montgomery to compel the seating of passengers without regard to race.”

As part of the lawsuit, Alabama filed a motion to produce many of the NAACP’s records, including its membership lists. While the NAACP produced most of the documents, it refused to hand over its membership lists.

The Supreme Court backed the NAACP, citing the First Amendment. Being associated with this locally unpopular cause could expose members to harm and thus discourage people from engaging in their political activities. Justice John Harlan II wrote for the majority, “Inviolability of privacy in group association may in many circumstances be indispensable to preservation of freedom of association, particularly where a group espouses dissident beliefs.”

Half a century later, dissident beliefs and unpopular groups remain under threat. The First Amendment tends to contract during wartime, and the pressures of the war on terror and the rise of the security state have resulted in bizarre interpretations of free speech under the Patriot Act. Among the many provisions of the Patriot Act, one in particular amended 18 U.S.C. 1960 to penalize “unlicensed money transmitting businesses”—a count included in the Shrem criminal complaint as well as the Liberty Reserve indictment. Years before the government turned its eye on libertarians and bitcoin exchanges, it prosecuted hawala money services—alternative systems of remittance, often used in Middle Eastern communities, that have existed for hundreds of years, long before modern banks or Western Union, let alone bitcoin.

As troubling as the hawala prosecutions should be for proponents of cryptocurrencies, the Liberty Reserve case is more of a reason to worry. Liberty Reserve was a centralized digital payments system—like bitcoin, but with a central operator. The defendants were indicted for money laundering and the operation of an unlicensed money-transmitting service—but the indictment itself focused less on the defendants’ actual conduct, and instead featured a bizarre obsession with the design of Liberty Reserve’s system, which “enabled” “multiple layers of anonymity.”

And as the government turns to both the money laundering and the money transmitting statutes to regulate and penalize entire systems of money transmission, both innovators and political dissidents should take notice.

The WikiLeaks financial blockade was possible because transactions were bottlenecked, with only a handful of institutions making payments to WikiLeaks possible in the first place. The proliferation of cryptocurrency has changed that—but the regulation of exchanges as money service businesses once again threatens to recreate that bottleneck. Additionally, the particulars of the money laundering statute and the requirements for money transmitting service licenses create obligations to verify the identities of customers and actively prevent them from engaging in anonymous, untraceable transactions shielded from government scrutiny.

Money is speech, as Citizens United would have us believe. And as immensely unpopular as that decision is, the court had a point—money is essential to political participation, and restrictions on the use of money in political activities can silence the cause of both the plutocrat and the dissident. Just as money can amplify the voices of the super-wealthy, starving out WikiLeaks with a financial blockade can force it to suspend publishing.

But if money is speech, and free speech can require a certain degree of privacy, even anonymity, particularly so when the speaker supports an unpopular political cause—then why don’t we have a right to anonymous payments?

There are many good reasons to reject that notion—even if the statute is being used in questionable ways, money laundering is still a real problem, and most of us are leery of giving the super-wealthy even easier ways to pour unlimited, anonymous amounts of money into the political system. But in this respect, bitcoin and other cryptocurrencies have hardly introduced a novel dilemma—they have merely forced a 50-year-old question made more complicated by more recent legal history.

As we see an uptick in prosecutions under the money laundering and money transmitting statutes, it is important not to simply dismiss anonymity as the realm of drug dealers and tax evaders. Do we really want to criminalize financial privacy, or the technologies that enable financial privacy? We will be lucky if Charlie Shrem is the last bitcoin startup CEO to be charged by the U.S. government—a hundred times luckier if we can avoid a cryptocurrency-themed redux of Liberty Reserve.

A mask in itself should not be a crime. Giving a man a mask should not be one, either. Yes, anonymity is desired by those whose activities disrupt the state—but sometimes disrupting the state looks like a bus boycott in Montgomery, Ala. There is tangible free speech potential in cryptocurrency, and it should not be easily dismissed.