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.
"Working at Hill Holliday was an eye-opening experience that exposed me to all the different facets of communication -- from creative advertising, to Internet marketing, to media buying and brand strategy. It was a valuable education," Fehrnstrom wrote in an email to TheStreet. Connors said Fehrnstrom did great work at Hill Holliday and was disappointed when he eventually left the agency to work for then-gubernatorial candidate Romney in 2002. Connors is an active Obama fundraiser: Records gathered by The Daily Beast show that he and wife Eileen have bundled between $50,000 and $100,000 for the president's 2012 run, and between $100,000 and $200,000 for the 2008 race. Fehrnstrom's fiercely loyal personality showed similar commitment to Connors in his fundraising for the Democratic Party. In fact, Federal Election Commission records show that the former ad agency spokesman made two $500 donations in 2001 for Kerry's 2002 Senatorial campaign. FEC records show $500 donated to the Kerry Committee on June 30, 2001. An identical contribution was sent to the Kerry campaign on Dec. 5, 2001. The FEC filing lists Fehrnstrom's employer as "Hill Holliday" under his second contribution. During Connors tenure as CEO, Hill Holliday jointly held accounts for advertising and for politics. Connors and Kerry are long-time friends. At the time Fehrnstrom made his contributions to Kerry's campaign, the former ad agency head was probably having a fundraiser for the senator and asked some of his staff to show support through a contribution, Connors recalled. A Romney campaign official said on background that the Hill Holliday CEO asked Fehrnstrom to write the check, and that he wants a refund. "Did I force him or anyone else to write a check? Never. If somebody ever said 'no' to me, I never held it against them," said Connors. "I never forced anybody to write a check, I'm very comfortable with that." Other Democratic operatives have expressed respect for Romney's trusted adviser beyond the $1,000 he gave to the party. "While Jack Connors is a well-known Democrat, they knew how to take care of their accounts ... and he was good to Eric," said Michael Goldman, a Democratic operative in Massachusetts. "Eric is a very talented kid, in fact, I was a little bit surprised when he slid out of there to go to work for Romney, but he always sort of wanted to go back into politics."
Phil Johnston, a Democratic strategist in Massachusetts who served as the state's Democratic Party chairman from 2000 through 2007, worked against Fehrnstrom as the aide worked for then-governor Romney. "He's a smart, tough political operative, and I think he's very good at what he does, and I think he's very loyal to Romney. I certainly don't agree with his politics, but I respect what he does professionally," said Johnston. When Romney returned from his post as CEO of the organizing committee for the 2002 Winter Olympic Games in Salt Lake City, Fehrnstrom left Hill Holliday to become spokesman for the Romney gubernatorial campaign. The reflections from Connors and Fehrnstrom on their time together read like a political bro-mance. Connors said that he was disappointed when Fehrnstrom came to his office to say he would be moving on. Connors called the 50-year-old senior adviser a talented young guy. In an email, Fehrnstrom reciprocated the feeling. "Jack Connors is a gifted businessman who built Hill Holliday into one of the best ad agencies in the country. He also happens to be among the nicest and most generous people that I know," said Fehrnstrom. They have kept in touch since their tenure together ended: Toward the end of then-Gov. Romney's term, Connors said Fehrnstrom sought his career council as to whether he should start his own political strategic planning firm or continue to work for campaigns directly. Fehrnstrom ended up following the governor to his failed 2008 presidential bid, and then started consulting firm The Shawmut Group with Beth Myers and Peter Flaherty -- two other close Romney aides. The Romney team has recently slogged through some of its most difficult days of the campaign, but the clever Romney operative is likely to land on his feet, regardless of whether Romney wins the election. Getting his $1,000 back from Sen. Kerry, which the Romney campaign official said remains a goal, could prove more difficult for Fehrnstrom. According to a person familiar with Federal Election Commission rules, the FEC only mandates a campaign to return a donation if a person makes an excessive contribution. In the case of Fehrnstrom's donations in 2001, he would have had to request the money back directly from Kerry and it is at the discretion of the campaign recipient. When asked if Fehrnstrom had requested Kerry to return the funds, Kerry spokeswoman Jodi Seth responded: "This is news to us." TheStreet asked Fehrnstrom in multiple emails about the $1,000 sum he gave to the Democratic heavy-weight's race, but he did not offer a response. "You don't often get compliments from Obama supporters about an Eric Fehrnstrom," Connors said with a chuckle. "I don't think people are waiting in lines to give him compliments, but I would. And the fact that he contributed -- perhaps at my request -- to Kerry shows he's also got a sense of humor." -- Written by Joe Deaux in New York. >Contact by Email. Follow @JoeDeaux