President Clinton looks at the computer screen as he participates in the Democratic Leadership Council/Excite On Line Town Hall Meeting, November 8, 1999 (Photo Credit: Paul J. Richards/AFP via Getty Images)

By David Kurlander

Twitter, Congress, and the FBI are scrambling for answers after a hack last week compromised the accounts of 130 prominent figures—including presumptive Democratic presidential nominee Joe Biden, President Obama, and Bill Gates—with Tweets asking for Bitcoin. The severity of the cyberattack raised questions for journalists and cybersecurity experts about the prospect of a more insidious social media breach on the eve of the election. The wide-ranging Internet reckoning evokes a turn-of-the-millennium takedown by a hacker codenamed mafiaboy of sites including Yahoo!, Ebay, and the then-fledgling Amazon. MafiaBoy, who turned out to be a 15-year-old Canadian amateur, shook to their core the Clinton administration’s accelerating plans for Internet diplomacy and public relations…

On February 7th, 2000, Montreal ninth-grader Michael Calce unleashed a series of Denial-of-Service (DoS) attacks on Yahoo!, then the world’s most trafficked site. Calce explained his methods in his memoir, Mafiaboy: The Portrait of the Hacker as a Young Man: “In a DoS attack, you bombard someone with an avalanche of server requests until his or her network is paralyzed. It’s as if you’ve sent so many people rushing into a small building that no one can get in or out.” Calce set up the attack, went to school, and returned home to find Yahoo! down around the world. Calce—as MafiaBoy—was a regular on the Internet Relay Chat network, an early form of instant messaging that was popular in the hacker community. He bragged about the attack and liveblogged his seven further operations over the next two days. The FBI, picking up on the IRC chatter, began a frantic search.

President Bill Clinton had just weathered Y2K, the catch-all term for fears surrounding the ability of computer programs to roll-over from 1999 to 2000. Although now cited as perhaps the greatest overreaction of the post-War age, Y2K was deadly serious for the administration. Way back in March 1998, Clinton appointed Office of Management and Budget veteran John Koskinen as Chairman of the President’s Council on Year 2000 Conversion, which oversaw $100 billion in domestic spending on corporate software updates that would reduce risk of millennial meltdown. On January 1, 2000, Koskinen, at a D.C. press briefing, triumphantly received a package of commemorative stamps he had sent to himself from Los Angeles the previous night—an indication that the automated elements of the postal service were still intact.  

Only a month after Y2K had passed largely without incident, MafiaBoy had triggered renewed alarms. As the Royal Canadian Mounted Police closed in on the young hacker and the FBI pursued errant leads to suspect Captain Zapp (who sent an 18-page manifesto claiming responsibility to MSNBC), President Clinton focused on the fallout.

On Valentine’s Day 2000, Clinton appeared with Wolf Blitzer on the first ever interactive presidential web interview. The Q&A broke CNN chat records with 10,400 participants, who heard Clinton respond to questions submitted in real-time. Clinton took time to specifically decry the DoS attacks, and, when asked about his favorite website, praised two of the platforms MafiaBoy had struck: “I love books, so I like And I’m fascinated by eBay, because I like to swap and trade, and it reminds me of the old kind of farmer’s markets and town markets I used to visit when I started out in politics in Arkansas so many years ago.” In an ironic moment, a savvy chat attendee stole the President’s “President_Clinton” username following a brief server crash, writing, “Personally, I’d like to see more porn on the Internet…Wolf, what about you?” Blitzer, thankfully, did not take the bait.

The following day, February 15th, Clinton re-branded an existent cybersecurity roundtable at the White House to be explicitly focused on MafiaBoy’s attacks. Top tech sector representatives—including those from the targeted sites—heard Clinton’s soothing words: “We ought to approach this with determination, And we shouldn’t be surprised that these things happen. It’s just a replay of what has always happened whenever there is a new way of communicating—a new way of making money—throughout human society.” 

At the end of the press briefing, a particularly booming journalist practically screamed a question asking whether the DoS attacks were an “electronic Pearl Harbor,” a reference to a popular warning given to Congress a decade earlier by Internet scholar Winn Schwartau. Clinton, looking perturbed, responded, “I don’t think it was Pearl Harbor. We lost our Pacific fleet at Pearl Harbor — I don’t think the analogous loss was that great.” 

Yet even if this wasn’t war, the action was swift. The very day after the roundtable, February 16th, FBI Director Louis Freeh and Attorney General Janet Reno testified before the Senate Appropriations Subcommittee on Commerce, Justice, State, the Judiciary and Related Agencies, arguing for steep budget increases for cybersecurity and expounding upon Clinton’s plan for a national “clearinghouse” for companies to share defensive strategies. Many of their clarion calls would be taken up by President Bush’s cybercrime czar, Richard A. Clarke.

In April 2000, the RCMP took MafiaBoy—whose identity as Michael Calce was withheld until his 18th birthday—into custody. He served six months in a youth home and is now a successful “white hat” hacker, helping organizations detect internal vulnerabilities. “I never expected to hear my handle broadcast on CNN, or to prompt the President of the United States to convene a summit with some of the country’s top technology and computer-security leaders,” he reflected in his memoir.

MafiaBoy may have been naïve to his own power, but the reverberations of his attacks were profound, stretching beyond the realm of domestic cybersecurity to Clinton’s foreign policy. During a crucial speech about China’s planned entry into the World Trade Organization in early March, Clinton, also showing some naivete and inspired by his own cybersecurity trials of the previous months, teased Beijing: “Now there’s no question China has been trying to crack down on the Internet…Good luck!” Clinton quipped. “That’s sort of like trying to nail jello to the wall.”

As the Twitter hack sparks another round of social media regulation and conversations over election integrity—as we now try to nail our own jello to the wall, if you will—the David and Goliath impact of MafiaBoy is a reminder of the continued corruptibility and unpredictability of the Internet.

Listen to this week’s episode of Lisa Monaco and Ken Wainstein’s new CAFE Insider podcast, United Security, to hear Lisa’s reflections on being in the room—as a staffer to Attorney General Janet Reno—during Clinton’s MafiaBoy roundtable. 

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