The Press Herald and Sunday Telegram editorial board was once generally viewed to have center-left political views. It endorsed the 2003 Iraq War, but has since criticized the war's execution. In Maine's 2006 campaign for governor, it endorsed John Baldacci, the incumbent Democrat, who was reelected. In the 2004 presidential election, the paper endorsed Democrat John Kerry, who won Maine but lost the national election. In 2008, it endorsed Barack Obama, who won both Maine and the general election.
However, under Richard Connor, the paper moved to the center, causing some in relatively liberal Portland to abandon the paper in favor of the city's free daily newspaper, The Portland Daily Sun, or for the Bangor Daily News, which made inroads into the Portland market. In 2010, it endorsed conservative Republican candidates (Dean Scontras and Jason Levesque) in both of Maine's congressional districts. They were both defeated by the Democratic incumbents, Chellie Pingree and Mike Michaud. For Maine's gubernatorial election that same year, it endorsed moderate independent former Democrat Eliot Cutler, a close friend of Connor, who came in second with 34% of the vote.