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.
"Literally, I would leave him messages just angry at him," McGregor recalled Thursday after police confirmed that Flanagan had died from a self-inflicted gunshot wound. " 'Just call me. Come on. Are you all right?' I think there were some things there — I don't know what it was — but he wouldn't open up."
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.
"You know there are certain moves that aren't going to work out because it was the nature of the sport, but he expected and wanted them all to work out," Duquette added. "He expected every player acquired to have the same work ethic, the same heart and desire that he possessed as a player — and that the other guys did that were part of the great Orioles clubs that he was on. It became a frustration for him at times. It would keep him awake at night."
Former Orioles manager Dave Trembley said he had spoken with Flanagan several times over the winter and called his death a "bad dream."
"He wanted to talk about the young guys we had," Trembley said. "He loved the Orioles. I think he really, really was hurt when he felt that he wasn't involved anymore. He just wanted to help."
Thorne said he developed a bond with Flanagan while calling games with him the past two seasons on the Mid-Atlantic Sports Network. He refused to blame his friend's death on Flanagan's disappointing tenure running the club.
"While there was disappointment, I don't think he ever thought of it as failure," Thorne said. "It was an effort that didn't succeed. It wasn't for a lack of effort and work at it. That's a big difference. I don't think everything that happened to him should be put on the fact that his time in the front office didn't get the results that he wanted. He was a much bigger person, a much stronger person."
Thorne said he was struggling to accept that he would not call this weekend's Yankees series with his friend as planned.
Flanagan was a stalwart presence during the Orioles' last run of extended success, which culminated with a World Series victory in 1983. After a standout career at the University of Massachusetts, where he also played basketball with Julius Erving, Flanagan seemed the successor to a line of Orioles pitching royalty.
The lefthander used a hard sinker and big, looping curve to win 23 games and the Cy Young Award as the Orioles rolled to the World Series in 1979. But he stoically pitched through arm and knee pains that would have benched many. Perhaps as a result, he had to get through the second half of his career more on guile than on great pitches.
Win or lose, he was known as one of the funniest men in baseball. After he retired in 1992, Flanagan found success as a broadcaster and pitching coach. Foss said Orioles owner Peter Angelos told him as early as 1994 that he saw something special in Flanagan, a combination of intelligence and magnetism that could make him a great executive. Angelos did not respond to interview requests Thursday.
In six years running baseball operations, first with Jim Beattie and then with Duquette, Flanagan oversaw clubs with a combined record of 430 wins and 541 losses.
McGregor recalled how Flanagan failed to return calls in the months after he lost his job. McGregor even mentioned his concerns to other former teammates such as Jim Palmer and Rick Dempsey.
"I said, 'Guys, I'm afraid. He's in a bad spot,'" McGregor remembered Thursday. "I was concerned about this back then."
Even so, nothing prepared friends for the news that started to spread Wednesday evening. They could not reconcile it with the Flanagan they had known, the flinty New Englander whose bone-dry quips could break up any room.
"I never saw that flame flicker at all," Foss said, reflecting on Flanagan's passion for baseball. "He loved hanging around the park, the environment of Orioles baseball. I probably watched 500 games with him, and he became a special person in my life. … This is a damn tragedy."