Jake graduated from Highland High School in 2008. His senior year he led his HS baseball team to the 2008 state championship. As a pitcher, he was 14-0 with a .08 ERA. His senior year he batted .422 with 15 homeruns. He holds numerous Highland High School baseball records.

In 2008 Jake was Gatorade Player of the Year, USA Today National Player of the Year, Louisville Slugger Award, All State Pitcher and Shortstop, Prep Baseball Player of the Year, and All State Football.

Jake was selected by the Milwaukee Brewers in the 1st round of the 2008 Major League Baseball draft (32nd overall). He made his major league debut in 2012 with the Kansas City Royals. His MLB stats as of 2015 are ERA 3.77, Wins-20, Losses-24, Strikeouts-350, Walks plus hits per inning-1-22. Jake is currently a starting pitcher with the Tampa Bay Rays.