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Mike Flanagan, who won the majority of his 167 games with the Orioles, went 26-27 in a short stint with the Blue Jays in the late 1980s. He is best remembered in Toronto for serving up Jose Canseco's fifth-deck home run in the 1989 AL Championship Series. ((Will Kirk/Associated Press))

Aside from being a longtime Baltimore Oriole, a Toronto Blue Jay for a short time and a Cy Young winner,  Mike Kendall Flanagan was self deprecating, witty, intelligent, a great storyteller, and to many who knew him, the funniest man in baseball.

He was all that and more during his 18 major league seasons.

The crafty left-hander/turned pitching coach/turned broadcaster/turned front-office type died Wednesday at age 59, found dead on a pathway on his Monkton, Md., residence from a self-inflicted shotgun wound to the head, a Maryland medical examiner reported Thursday.

Flanagan, the Harvard grad and two-sport athlete at the University of Massachusetts at Amherst — he also played basketball — had a gift for one-liners and anecdotes, wrote ESPN.com's Buster Olney on Thursday.

Flanagan with Blue Jays

Longtime Baltimore Orioles left-hander Mike Flanagan pitched two full seasons and parts of two others in Toronto, recording a 26-27 overall record. Here's a season-by-season breakdown of his time in Canada.

 Year  W  L  ERA  GS  IP  SO
 1987  3  2  2.37  7    49.1  43
 1988 13  13  4.18  34  211  99
 1989  8  10  3.93  30  171.2  47
 1989 (playoffs)  0    1  10.38    1      4.1    3
 1990  2    2    5.31    5    20.1    5

While Blue Jays fans may have seen glimpses of this side of Flanagan if they caught a pre- or post-game interview during his two full seasons and parts of two others with the team, he is best remembered in Toronto for two on-field performances.

After a slow start to the 1987 season in Baltimore, Flanagan soon found new life in Toronto after the Blue Jays acquired him for the stretch drive, sending relief pitcher Jose Mesa and starter Oswaldo Peraza to the O's.

In seven regular-season starts, he went 3-2 with a 2.37 earned-run average and 43 strikeouts in 49 1/3 innings pitched. Eleven of those innings were used for the southpaw's biggest regular-season start of his career on the next-to-last day of the season.

With the Blue Jays holding a one-game lead over Detroit atop the American League East, Flanagan outlasted Tigers ace Jack Morris, limiting his opponent to two runs. Out of the game, Flanagan watched the Blue Jays bullpen yield the winning run in the 12th inning. The next day, Detroit won the game and the division.

Forgettable outing

Two years later, almost to the day, Flanagan made his last playoff appearance — a forgettable 4 1/3 innings in Game 4 of the American League Championship Series against the Oakland Athletics.

The 37 year old served up three home runs, including a 480-foot shot to Jose Canseco, the first hit to reach the upper deck at Rogers Centre, which was called Skydome then.

The prodigious blast rendered many in the crowd of 50,076 silent and helped lift the A's to a 6-5 win. Oakland went on to win the next game 4-3 and the best-of-seven series in five games.

Flanagan never recovered from that disappointment, lasting just five starts in 1990 (5.31 ERA) before Toronto released him, leaving town with an unflattering 26-27 record overall.

Re-inventing himself as a highly effective set-up man, the New Englander fashioned a 2.38 ERA and three saves in 64 games in 1991 with Baltimore before an 8.05 ERA in 42 appearances in '92 drove him to retirement.

As tough as leaving the game must have been for such a competitor, it's a good bet Flanagan found some humour in it all.

Perhaps he recalled that day in 1984 when he was getting hit all over the ballpark in Osaka, Japan.

In his blog Thursday, Richard Justice of the Houston Chronicle wrote of seeing Flanagan in the Orioles' clubhouse about an hour or so later that day, saying by that time the pitcher was polishing his lines.

Justice wondered if Flanagan could have broken out his spit ball that day. Apparently, he had perfected one but never used it in game action.

"I couldn't live with myself if I did," the pitcher said.

Sadly, years later, he couldn't live with himself, period.