[2] Also, the Evening Express of Portland was published by Guy Gannett until it was phased out in favor of the Press Herald.

[8] The Bollard described the Switch in 2008 as a "free pile of cheap wrapping paper", describing the paper as "following fads, exploring yoga and toiling away at an endless list of home improvement projects between marathon bouts of Art Walking and pandering to potential advertisers.

[1] PressHerald.com, on top of the Press Herald itself, hosts the Times Record and the Forecasters, American Journal, Lakes Region Weekly, and the Mainely Media papers.

It sold its television stations to Sinclair Broadcasting, and the newspapers to The Seattle Times Company,[11] for a price later reported at around 213 million dollars.

[19] On 15 June 2009, MaineToday Media was formed with the sale finalization of the Blethen papers; the new company was headed by Maine native Richard L. Connor, publisher of the Times Leader in Wilkes-Barre, Pennsylvania.

[25] Financial details of the sale were not released, though a Seattle Times report estimated them at less than half the $213 million paid in 1998.

"[12] MaineToday promised that it could put its newspapers on a sound financial footing, but over the next two and a half years there were more than 160 job cuts at the Portland Press Herald, the company was sued for failing to pay a paper bill, and the local guild president said his members "feel their investment in Rich Connor was squandered and they're angry about it.

In April 2013, Connor was accused of misappropriation of about $530,000 of the newspapers' funds for personal expenses and unauthorized salary increases for himself.

"[27] In January 2012, Massachusetts businessman Aaron Kusher, who had previously made an unsuccessful 200 million dollar bid to buy The Boston Globe, led a group that bought a controlling interest in MaineToday Media for an undisclosed price.

[31] In 2015, Sussman sold MaineToday Media to Reade Brower, a Maine printer and newspaper owner.

[37] In Spring 2018,[2][38] MaineToday purchased the Biddeford Journal Tribune and the Brunswick's The Times Record,[39] which became parts of the Alliance Press media group.

[44] In 2020, Masthead announced it would stop printing Monday editions for four out of five of its daily newspapers, opting instead for digital-only Monday editions, a change affecting the Portland Press Herald, Morning Sentinel, Kennebec Journal, and Sun Journal newspapers.

[56][57] Despite the criticism, the News Guild of Maine greeted the changes with relief,[58] stating that they were grateful Brower chose to sell to a nonprofit.

Their president, Bill Neimitz stated: "Our goal going into this was for the Press Herald and all the other Masthead Maine properties to convert to nonprofit ownership," and as the deal was completed with a not-for-profit entity, Neimitz was satisfied, stating on behalf of the foundation that they were "absolutely thrilled" with the outcome.