Government investigations of crimes has been transformed by modern technology.  Viewers of HBO’s original series “The Wire” will recall how Detective McNulty of the Baltimore Police Department salivated in amazement at the sleek wiretap equipment employed by federal law enforcement. Yet wiretapping phones like that seen in The Wire are archaic relics of the past, with law enforcement now having the capability to wiretap email transmitters, social networking sites, and peer-to-peer communications. As the NYTimes reported in 2010, federal law enforcement officials were pushing for Congress to pass regulations that would make it easier to wiretap the Internet.

Wiretaps are now being used in investigations beyond the scope of illegal drug transactions.  The Securities and Exchange Commission (“SEC”) is cracking down hard on illegal insider trading cases, all with the aid of confidential witnesses and wiretaps.  In December, U.S. District Judge Richard J. Holwell sentenced Raj Rajaratnam to the “longest-ever term imposed in an insider trading case,” at a whopping eleven years in prison.  Mr. Rajaratnam’s sentencing will likely be the first of many success stories for the government as federal prosecutors employ wiretaps that accumulate evidence in ways lawyers of yore fantasized about.

Lawyers and lawmakers are scrambling to make sure that regulations keep up with the fast pace of technology advancement. However, a failure to understand the complexity of the wiretap technology and pertinent regulations may bring harsh repercussions.