NEW YORK ( TheStreet) -- The pluckiest Republican among Mitt Romney's inner circle, Eric Fehrnstrom, has had a reputation for being a thorn in the side of the Democratic Party. A senior adviser who has served Romney since his days as Massachusetts governor, Fehrnstrom was widely known among state politicos for his service to conservatives and his aggressive demeanor. It's a competitive spirit, to put it mildly, that has been on display as Romney's president run took shape and the former muckraking journalist attracted attention from the national press. Fehrnstrom spent the late 1980s and early 1990s working for The Boston Herald -- then owned by Rupert Murdoch -- where he was known as a shrewd reporter who chased down tabloid-friendly stories that ended one candidate's aspirations to run for governor and damaged a former Democratic presidential nominee's chances at victory.
Less exposed, though, is a detour Fehrnstrom took to the dark side during his rise up through the ranks of the GOP: he worked for a major Democratic Party fundraiser. He even made campaign contributions to former Democratic presidential candidate Sen. John Kerry. Fehrnstrom dropped journalism for politics in 1994 and went to work for then-Massachusetts Treasurer Joseph Malone. He stuck with Malone through a 1998 failed primary run against then-GOP governor Paul Cellucci. And that's when the detour to the dark side began. Soon after his defeat, Malone dropped out of politics and Fehrnstrom pivoted to one of the strongest Democratic backers in the state for a job. He went to work for advertising agency Hill Holliday at the beginning of 1999 as the company's new spokesman. Jack Connors, the then-CEO of Hill Holliday who calls himself a dyed-in-the-wool Democrat, said it was a reference from Ben Cammarata, the former CEO of TJX Companies ( TJX), a client of the ad agency at the time, which led him to Fehrnstrom. "I met him, liked him and hired him," said Connors. "I don't particularly care what people's politics are, I just want to know whether they can hit, you know?" It was obvious -- maybe painfully so to an influential Massachusetts Democrat -- that based on his time at the Herald and years with Malone, Fehrnstrom possessed the chops Connors desired. The well-known aphorism imprinted in the operating manual of Western civilization's political chess masters advises the powerful to keep their friends close, and their enemies closer. Fehrnstom and Connors, though, simply say they worked well together.