Pierce graduated from St. John’s High School in Shrewsbury, Massachusetts and from Marquette University with a journalism major in 1975.

Pierce’s first job was as a forest ranger for the Commonwealth of Massachusetts. He wrote for Worcester Magazine in the 1970s, where he covered the Blizzard of 1978. In the 1980s and ’90, he was a staff reporter for the Boston Phoenix and, later, a sports columnist for the Boston Herald.

Pierce is currently the lead political blogger for Esquire, a position he has held since September 2011. He also writes for ESPN’s Grantland. He has also written for The New York Times, the Los Angeles Times, the Chicago Tribune, the Boston Globe Sunday magazine, the Milwaukee Journal-Sentinel, Sports Illustrated, The National Sports Daily, GQ, and the e-zine Slate as well as the Media Matters blog Altercation, hosted by historian/pundit Eric Alterman.

Pierce makes appearances on radio as a regular contributor to NPR programs Only A Game and Wait Wait…Don’t Tell Me!. Recently Pierce has begun making weekly appearances on the Stephanie Miller Show. He represented the Globe on several occasions on ESPN‘s Around the Horn and often co-hosts with Bob Ryan on NESN‘s Globe 10.0.