Winker was born in Buffalo, New York and grew up in Niagara Falls, New York, before moving to Orlando, Florida at the age of seven. Winker was drafted by the Cincinnati Reds in the first round of the 2012 Major League Baseball draft out of Olympia High School in Orlando, Florida. As a junior at Olympia, he had a.509 batting average. He had committed to play college baseball at the University of Florida for the Florida Gators, but chose to sign with the Reds rather than attend college. Winker made his professional debut for the Billings Mustangs in 2012. In 62 games, he hit.338/.443/.500 with five home runs in 228 at-bats. Prior to the 2013 season, Winker was ranked by Baseball America as the Reds sixth best prospect. He played the season with the Dayton Dragons where he became a Midwest League All-Star and Home Run Derby champion. He hit.281/.379/.463 with 16 home runs in 417 at bats over 112 games. Before the 2014 season, he was ranked by Baseball America as the Reds fourth best prospect. He started the season with the Bakersfield Blaze. In June he was promoted to the Double-A Pensacola Blue Wahoos. In July, Winker played in the All-Star Futures Game, going 1-2. His season came to an end in July after suffering a partially torn tendon in his right wrist in a car accident. In 74 games, he hit.287/.399/.518 with 15 home runs and 57 runs batted in. Winker returned after the season to play in the Arizona Fall League. Winker spent 2015 with Pensacola, where he posted a.282 batting average with 13 home runs and 55 RBIs. The Reds added Winker to their 40-man roster after the 2016 season. He began the 2017 season with the Louisville Bats of the Class AAAInternational League, and was promoted to the major leagues on April 14.. In 2017, Winker batted.298 with seven home runs in 47 games played. Winker began 2018 with Cincinnati, and was a starting outfielder before a right shoulder injury in July ended his season. Prior to his injury, he slashed.299/.405/.431 with seven home runs and 43 RBIs.
