After being traded to the Boston Red Sox in 1923, Flagstead became one of the leading center fielders in the sport, with a combination of speed, a strong arm and a reliable glove.
He also set an American League record by starting three double plays as an outfielder in a single game, including two runners thrown out at home plate.
[3][2] With arms and shoulders strengthened from his work as a steam fitter, Flagstead also competed briefly as a lightweight boxer while living in Washington.
[5] Flagstead did not begin playing professional baseball until age 24 when he signed with a team from Tacoma of the Northwest League.
[1] Late in the 1919 season, teammate Ty Cobb predicted that Flagstead was "destined to be one of the greatest hitters in the business.
[1] In 1921, the Tigers were loaded with outfielders, including 1921 batting champion Harry Heilmann, Ty Cobb, and Bobby Veach.
[16] In 1922, the Tigers added shortstop Topper Rigney and outfielder Bob Fothergill, resulting in a further loss of playing time for Flagstead.
However, the Tigers roster of hard-hitting outfielders by then included Cobb, Heilmann, Veach, Heinie Manush and Bob Fothergill.
Finally, on April 28, 1923, the Tigers traded Flagstead to the Boston Red Sox in exchange for Ed Goebel.
[18] Flagstead appeared in 109 games for the 1923 Red Sox, 98 of them as the team's starting right fielder, and led all American League outfielders with 31 assists and eight double plays turned.
[1] After the 1923 season, Flagstead received national press coverage for an automobile trip with his wife and brother after picking up a new Buick sedan at the factory in Flint, Michigan, and driving on unpaved, muddy roads to their home in Olympia, Washington.
That year, he compiled a .307 batting average and .401 on-base percentage and ranked among the American League leaders with 106 runs scored (sixth), 77 bases on balls (eighth), and 11 times hit by a pitch (third).
For several years, he has been flanked by rookie or crude gardeners at Fenway field and it has been Ira's voluntary task to try to instill in them some idea of how to play the outfield without wearing a mask and protector to avoid being hit by misjudged fly balls.
In a ceremony before 17,000 fans at Fenway Park, the lieutenant governor of Massachusetts presented Flagstead with $1,000 in gold, a new automobile and other gifts for him and his wife.
[32] After his release by Portland, he signed with the Seattle Indians, also of the PCL, where he concluded his professional baseball career in the last portion of the 1931 season.
[4] After his professional career ended, Flagstead continued to live in Olympia, where he managed a local baseball team that advanced to the Timber League championship playoffs for three consecutive years.