Later he was chosen by the Milwaukee Brewers team in the 26th round of the 2005 Major League Baseball draft, but he decided to move to the Texas Christian University, where he studied sport psychology and played for the Horned Frogs baseball team.

He led college baseball with 14 wins during his sophomore year and later won the title of the Mountain West Conference Pitcher of the Year award. Afterwards, he was named a Second-Team College Baseball All-American. In the 2006 he joined the United States national baseball team In Cuba he showed a very good result and thanks to his skills the team win the World University Baseball Championship.

He joined by the Baltimore Orioles team in the 2007 and got $1.1 million signing bonus during the fifth round of the Major League Baseball draft. He made his first appearances in the Arizona Fall League during the match against the Phoenix Desert Dogs in the same year. He made 16 scoreless innings, as well as striked out 16 over 14 appearances, and in the end he helped lead the Desert Dogs team to the Arizona League championship and reached a good stats result.

He made his main league appearance in the 2010, playing against the New York Yankees team at the Camden Yards. Both games in the end resulted in victories for the Baltimore Orioles team. In the 2013 he began the season with s starts for the Orioles, posting a 1–1 record and a 6.63 ERA.

In the same year he was traded along with another player Pedro Strop to the Chicago Cubs team. Chicago debut, started with one run in six innings, earning a no-decision in the 3–2 loss. He took no-hitters into the 7th or 8th innings, three times in the next season.

During the game against the Red Sox team in the 2014, he took a no-hitter again into the 8th until Stephen Drew singled to lead off the inning. He pitched a complete game victory on July of the 2015 with the Chicago White Sox team at Wrigley Field. It was his the 3rd of his major league career game as well as the 2nd complete game of the season. In the same year he won the NL Cy Young Award. Recently, he signed a contract for the 2017 baseball season.

He resides in Austin, Texas along with his family. He is married to Brittany Arrieta. Jake and his wife are blessed with two beautiful kids named Cooper and Palmer. He earns a massive salary of $10.7 million dollars and has a net worth of 20 million dollars. He is available on Twitter.