Once admired in baseball for his toughness on the pitching mound and his droll wit off of it, Flanagan seemed to disappear after he lost his job as Orioles executive vice president in 2008.
McGregor thought his friend had taken a turn for the better this year. Flanagan seemed rejuvenated when calling Orioles games on television or swapping baseball tales with the club's manager, Buck Showalter.
That made it all the more difficult for McGregor and other friends to process the news of Flanagan's suicide. "I am just shocked," McGregor said. "I thought he was through all that."
Flanagan's body was found Wednesday afternoon at his home in Sparks. His wife, Alex, was out of town but sent a neighbor to their house in the 15000 block of York Road after she didn't hear from her husband all day Wednesday. Police said she had last spoken to an upset Flanagan about 1 a.m.
The neighbor, unable to find Flanagan, called 911. Police found Flanagan's body on a trail about 250 feet behind his home about 4:30 p.m.
Police said that Flanagan, 59, appeared to have shot himself in the face, making identification difficult and causing official confirmation of his death to be delayed. Flanagan did not leave a note, police said, but they added that he had apparently been upset about financial issues. Police said that Alex Flanagan had also called 911 in June, asking officers to check on her husband.
Flanagan's family issued a brief statement on Thursday, saying: "We thank you for your support and kind words at this difficult time. Thank you for respecting our privacy as we grieve. A private memorial will be held at a later date."
Friends said they had no inkling that Flanagan might be facing financial difficulties and, recently, had seen little indication that he was depressed.
"Not at all," said former Orioles executive Joe Foss, who began a close friendship with Flanagan when he came to the club from the business world in 1993.
Foss works about a mile from the Flanagan home and noticed his friend sitting at a stoplight recently. He began tailgating Flanagan, prompting the former pitcher to open his sunroof and waggle a middle finger. A few seconds later, Foss' cellphone vibrated with a call from Flanagan, and the two talked merrily for the rest of a 30-minute drive downtown.
Foss said he saw the joy in Flanagan's face as he announced Orioles games with Gary Thorne and heard the excitement in his voice over a growing bond with Showalter. The two were working on lunch plans for this weekend with Jim Duquette, who shared leadership of baseball operations with Flanagan from 2005 to 2008.
"We didn't see any indication of this coming," Foss said. "Mike was just his normal self."
Foss said Flanagan was hurt by the end of his run as the club's top baseball executive, after his contract wasn't renewed. He spent more than 30 years with the Orioles as a Cy Young Award-winning pitcher, an announcer and a coach, and he yearned to restore the franchise to its past glory.
"The circumstances around a suicide are very complex," Foss said. "No doubt he had multiple reasons. Could the situation with the Orioles have been one of the factors? It could well have been."
Foss said Flanagan had made no mention of financial troubles. A search of court records found no evidence of bankruptcy, foreclosures or other financial issues.
Duquette spoke to Flanagan on Tuesday night and said he detected no hint of what was to come. He rushed to his friend's house the next afternoon after a reporter's call alerted him that a body had been found there. Duquette's heart sank when he saw police cars.
"He cared so much and that was most times a good thing, but oftentimes, it was tough on him because he tended to pay attention to that criticism a little more," Duquette said in reflecting on Flanagan's time as a baseball executive.