Tenure with the Baltimore Orioles
|Baltimore Orioles – No. 3|
|Infielder, Designated hitter|
July 27, 1986 |
|Bats: Left||Throws: Right|
|April 7, 2012 for the Baltimore Orioles|
(through August 16, 2014)
|Runs batted in||67|
Flaherty was held back one year at Lyman Moore Middle School at the insistence of his family to perform better at the High School level. Flaherty graduated from Deering High School in 2005. In 2004, he led Nova Seafood to the American Legion World Series Championship, as well as winning the Telegram League batting title. He was a 2005 American Baseball Coaches Association Preseason All-American, also winning Maine's Mr. Baseball award. He was also named Maine Gatorade High School Player of the Year as a senior at Deering High School.
Ranked the 141st-best professional prospect by Baseball America, he chose to attend Vanderbilt University, where he played college baseball for the Commodores in the Southeastern Conference (SEC) of the National Collegiate Athletic Association's Division I.
As a freshman, Flaherty was named an honorable mention Freshman All-American. In sixty-two games, Flaherty had a .339 batting average with 49 RBIs, 19 doubles, two homers and an on-base percentage of .421, leading the team with 22 multi-hit and 15 multi-RBI games.
As a sophomore, Flaherty had a .381 batting average with 57 RBIs, 23 doubles, four homers and an on-base percentage of .438 in 67 games. He was named Second-team All-American selection by Rivals.com and the American Baseball Coaches Association (ABCA). He was also selected to the ABCA All-South Region Team as well as Second-Team All-SEC.
The Chicago Cubs selected Flaherty in the first round (41st overall) of the 2008 Major League Baseball Draft. In four seasons in both A and AA. Flaherty played 322 games with a .279 batting average, on-base percentage of .347, slugging percentage of .455, 182 RBIs, 38 homers and 79 doubles. He had his two best professional seasons in 2009 and 2010.
The Baltimore Orioles selected Flaherty from the Cubs in the Rule 5 Draft on December 8, 2011. He made the Orioles' Opening Day roster. He scored his first run in the Major Leagues on April 14th against the Blue Jays in Toronto.  He hit his first MLB home run as part of three consecutive home runs off Colby Lewis of the Texas Rangers to start the first inning of the first game of a May 10, 2012 doubleheader at Camden Yards. Teammates J. J. Hardy and Nick Markakis followed with home runs.
On September 28, 2012, he hit his first career grand slam off Boston Red Sox pitcher Aaron Cook. On October 10, 2012, Flaherty hit a home run in Game 3 of the 2012 American League Division Series. Flaherty had his first multi-home run game on June 23, 2013 against the Toronto Blue Jays.