The Pinkerton Thugs formed in July 1994 in Kennebunkport, Maine, under a number of different names but officially became the Pinkerton Thugs in March 1996 (taking their name from the infamous Pinkerton National Detective Agency). The band, which initially consisted of drummer/vocalist Paul Russo, guitarist/vocalist Micah Smaldone and bassist James Whitten drew influence from punk bands such as Sham 69, the Clash, Conflict, and Crass as well as Woody Guthrie's political ballads. They were known for their spirited live performances as well as their radical anarchist political views. Attempting to put their ideas to action, members of the band formed a now-defunct collective called the Anarchist Liberty Union which set out to distribute anarchist literature for free and establish better communication between activists. During most of the band's existence, Paul Russo was also a member of Boston band The Unseen, whom the Thugs often played shows with.

Their recorded debut was a 7 E.P. titled Life, Liberty, and the Pursuit Of Shit that was self-released on the band's own Police Records in the U.S. in August 1996 and re-released by Nefer Records in Canada in 1997. In addition to that record, The Pinkerton Thugs released two full albums (The Pain and The Pinkerton Thugs on V.M.L. Records in 1997 and End Of an Era on Go Kart Records in 2000) a split 7 record with the Ducky Boys on Police Records, and a 7 on Go Kart Records titled The Times. The bands later recordings saw Paul Russo playing both drums and additional guitars on the songs he composed and sang, while Tommy Von who joined the band in 1998, played drums live. Shortly after the recording of End Of An Era in early 1999 Smaldone left the band, and Paul Russo became the band's sole lead vocalist. The band played a handful of live gigs with Scott from The Unseen and Bill Brown of Crash and Burn filling in on lead guitar before James Lynch of The Ducky Boys joined as a permanent member. He only played one show with the band before he left to join the Dropkick Murphys.

Break-up and subsequent projects

Pinkerton Thugs played its last show in February 2000 at the Karma Club in Boston, Massachusetts. End of an Era was released posthumously in June 2000, some 18 months after it was recorded. The band officially disbanded in October of that year, announcing their break-up via their website.

Following the band's demise Micah Smaldone and Tommy Von formed a hardcore band called Cops and Robbers which broke up in 2001. Smaldone has subsequently released numerous solo albums under his full name Micah Blue Smaldone and played guitar with Out Cold, the Shods, The Racketeers, and Fire on Fire. Tommy Von went on to play in Cut the Shit, The Prowl, and Ironsides. Paul Russo continued to play with The Unseen before leaving in 2003 and writing and recording his own music under a number of names including Paul and The Strings, The Strings, and Americana Romantic. He also played guitar with Boston punk band The Vigilantes from mid-2000 until their breakup in early 2002. James Lynch has continued to play with Dropkick Murphys since 2000.

Reunion

The Pinkerton Thugs officially got back together in 2008 and are currently active. Busy with their other projects, neither Micah Blue Smaldone nor James Lynch were available to participate in the reunion, so Mike Rufio Kadomiya joined the band as second guitarist. It was announced in December 2011 that The Pinkerton Thugs had signed with Jailhouse Records. Founding member James Whitten along with longtime drummer Tommy Von left the band in early 2012. , Mike Kadomiya who had been involved with the reunion lineup left as well. Paul Russo recruited Johnny Noise, Tommy Collins, and Vlad Wormwood as their replacements for a U.S. tour in the summer of 2012. A second split 7 with the Ducky Boys, recorded before Tommy Von and Mike Kadomiya left the band, was released in August 2012. The band has been inactive since.