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Jay Jackson: From Ninth-Round Pick to 20 Years in Professional Baseball

Jay Jackson was drafted by the Chicago Cubs in the ninth round of the 2008 MLB Draft. He never played a game for the Cubs.

Instead, Jay spent nearly two decades grinding through professional baseball — six MLB teams (San Diego Padres, Milwaukee Brewers, San Francisco Giants, Atlanta Braves, Toronto Blue Jays, Minnesota Twins), four years playing in Japan (Hiroshima Toyo Carp, Chiba Lotte Marines), countless minor league stops, roster cuts, releases, and the constant uncertainty of being a journeyman.

His path wasn't straight. He started as a starting pitcher, transitioned to the bullpen to…

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