Lynn Sweet

In 1999, when Barack Obama was running for the seat in the House of Representatives, he paid a visit to Sweet and gave her a copy of his book, Dreams from My Father, which she says she put on a bookshelf and never opened it up until June 2004, as his popularity rose and he had given his speech at the Democratic National Convention. In a 2008 interview, Sweet said, "Obama came in and had a very lucky break to come in 90-something, make some of the right connections, and have an opening."[13] Unimpressed with his rise in popularity, she went on to add:

"He returned to Chicago and worked with a law firm that gave him a lot of political network advantages, and started looking around for some office to run for, found this opening in the State Senate where he put himself in it. Now that’s not coming through the rough-and-tough of Chicago politics. And then once he knocked his opponent off the ballot, he represented a safe Democratic district, and that if he chose to, he could have represented until he stopped working. O.K.?"

Sweet would become known as one of Obama's toughest critics. In February of 2007, when he announced his Presidential bid, Sweet wrote in the Sun-Times, "Sen. Barack Obama (D-Ill.) used campaign donations generated by PACs and lobbyists to bankroll the birth of his White House bid — though he’s banning that money for his presidential 2008 race."[16] A reminder that he had accepted PAC money, when he ran for the House seat.

in 2008, Jim Romenesko wrote about Sweet,[17] in an article titled: Sun-Times’ Sweet is an “important voice,” thanks to Obama:

"Prior to this year’s political season, Lynn Sweet “was a largely unknown tabloid reporter from a regional newspaper who had never seriously covered a presidential campaign,” writes John Koblin. But with Barack Obama‘s ascent, the Sun-Times reporter/columnist has suddenly emerged as one of the most important voices in the campaign. Newsday’s Glenn Thrush says: “Of all the people who cover Obama, she’s the one who holds him most accountable."

Arianna Huffington, of the Huffington Post, descrbed how "Sweet once took a room at the Beverly Hilton hotel, where Obama was holding a big presidential fundraiser. She booked the room so she could see who was going in and out."[11]

When NorthStar news reported on President-elect Obama's first press conference, Sweets name was invoked: "Despite the serious tone of the news conference, the president-elect appeared relaxed and joked with reporters on several occasions. When he called upon a local journalist, Lynn Sweet of the Chicago Sun-Times, and noticed her arm was in a sling, he asked what had happened. When Sweet replied that she had injured her shoulder en route to Obama’s victory celebration in Grant Park, President-elect Obama smiled and said, “I think that was the only major incident during the entire Grant Park celebration."[18] She continued her tough reporting throughout his time in office and frequently speaks about her experience covering his administration.[19][20][21]