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Eric Fehrnstrom's Journey to The Dark Side

"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."

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