A gunman, whom officials said had a vendetta against the newspaper, stormed into the Annapolis, MD newsroom with a pump-action shotgun and opened fire.
Police identified the dead as John McNamara, 56; Robert Hiaasen, 59; Wendi Winters, 65; Rebecca Smith, 34; and Gerald Fischman, 61.
Copies of the letter were mailed to the Baltimore Circuit Court house, the state court of special appeals and the law firm, according to Ann Arundel County Police, who are investigating the mailings.
In 2016, for example, it was flown at half-staff 53 times, including after mass killings in Orlando and Brussels.
On Friday, a judge ordered that Ramos, 38, remain in custody and be held without bond on five counts of murder as Ramos appeared via a video feed from a detention center.
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Phil Davis, a Capital Gazette crime reporter, recounted how he was hiding under his desk along with other newspaper employees when the shooter stopped firing, the Capital Gazette reported on its website.
Mr Trump had ordered flags lowered for recent mass-shootings at Florida and Texas high schools and Mr Buckley said the newspaper massacre "was an attack on freedom of speech".
But during the flight he also criticised reporters, saying some are "bad", and told us: "The press has treated me very badly". "Is there a cutoff for tragedy?"
Hours later, an overflow crowd gathered to remember journalist Rob Hiaasen and his four colleagues who were shot to death by a gunman who blasted his way into the Capital Gazette's newsroom. "I guess they didn't treat me badly enough", Trump said, calling the shooting rampage a "disgrace".
Tronc is the parent company of The Baltimore Sun Media Group, which includes the Capital. The way Trump sees it if people are mad at the press they're less likely to believe he's as terrible as everyone says he is.
The Sun said the letters were dated June 28, the day of the shootings.
The correspondence sent to the newspaper's former attorney also included an attachment, the Sun reported, addressed to the judge who had written a sharp opinion against Ramos as part of the defamation case.
Ramos' conflict with the newspaper stems from a complaint a former high school classmate he barely knew filed against him in 2011.