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Before 2020 spring training, Jennings retired from playing professional baseball.

On February 15, 2019, Jennings signed a minor league deal with the Los Angeles Angels. The Angels released him on March 26.

On April 15, 2019, Jennings signed a minor league deal with the Washington Nationals. He had his contract purchased on April 30. Jennings posted a 13.50 ERA over eight games with the Nationals before being designated for assignment on May 20. He elected free agency on May 22.

On July 8, 2019, Jennings signed a minor league deal with the New York Yankees. He was released by the Yankees on August 13, 2019.

Jennings signed with the Milwaukee Brewers on March 30, 2018. He elected free agency on November 30, 2018.

On July 27, 2017, the White Sox traded Jennings to the Tampa Bay Rays in exchange for first baseman Casey Gillaspie. He was released on March 26, 2018.

On August 7, 2014, Jennings was pitching in relief against the Pittsburgh Pirates when Jordy Mercer hit a line drive that struck Jennings in the head, inflicting a concussion in the process. Jennings was kept overnight in a Pittsburgh hospital for observations instead of accompanying the Marlins to Cincinnati for their next series against the Cincinnati Reds after the game. Jennings later thanked Pirates fans on Twitter for their support after the crowd at PNC Park gave Jennings a standing ovation when he was carted off the field and gave the crowd a thumbs-up. He returned to the Marlins shortly thereafter, passing concussion protocol and sustaining no permanent injury.

The Marlins traded Jennings to the Chicago White Sox on December 11, 2014, in exchange for André Rienzo.

He made his professional debut that season for the Jamestown Jammers of the Class A-Short Season New York–Penn League.

Jennings began the 2012 season with the New Orleans Zephyrs of the Class AAA Pacific Coast League. In nine appearances, he had a 2.08 ERA.

The Marlins promoted Jennings to MLB on April 30, 2012, and he pitched a scoreless inning in relief in his debut that day.

Across three levels of minor league baseball in 2009, Jennings had a combined 1–2 record, six saves, and 2.15 ERA in 45 games overall, allowing with 26 walks and while striking out 69 batters in 62⅔ innings pitched for the Greensboro Hornets of the Class A South Atlantic League, the Jupiter Hammerheads of the Class A-Advanced Florida State League, and the Jacksonville Suns of the Class AA Southern League. Baseball America rated Jennings as the Marlins' fourth best pitching prospect, and 13th best overall. Returning to Jacksonville in 2010, Jennings was suspended for 50 games for violating minor league baseball's policy banning the use of performance-enhancing drugs. The Marlins added Jennings to their 40-man roster after the 2011 season to protect him from the Rule 5 draft.

Jennings attended the University of Nebraska, where he played college baseball for the Cornhuskers. In 2008, he played collegiate summer baseball with the Cotuit Kettleers of the Cape Cod Baseball League. He was drafted by the Marlins in the ninth round of the 2008 MLB draft.

Though born in Berkeley, California, Jennings was raised in West Des Moines, Iowa. There, he attended Valley High School. Playing for the school's baseball team, he led the team to back-to-back state championships in 2004 and 2005. As a senior in 2005, Jennings pitched to a 9–0 win–loss record and 0.85 earned run average (ERA), earning All-State honors.

Daniel Lee Jennings (born April 17, 1987) is a former American professional baseball pitcher. He played in Major League Baseball (MLB) for the Miami Marlins, Chicago White Sox, Tampa Bay Rays, Milwaukee Brewers, and Washington Nationals. He also played college baseball for the Nebraska Cornhuskers of the University of Nebraska.