He has previously played in MLB for the Cincinnati Reds, Seattle Mariners, Milwaukee Brewers, and Washington Nationals.

Winker was born in Buffalo, New York, and lived nearby in Niagara Falls before moving to Orlando, Florida, at the age of seven.

[6] He played the 2013 season with the Dayton Dragons[7][8] where he became a Midwest League All-Star and Home Run Derby champion.

[12][13] His season came to an end in July after suffering a partially torn tendon in his right wrist in a car accident.

Winker began 2018 with Cincinnati, and was a starting outfielder before a right shoulder injury in July ended his season.

[21] In 2019 for Cincinnati, Winker played in 113 games with a batting line of .269/.357/.473 to go along with a career-high 16 home runs as well as 38 RBI.

[24] On June 6, 2021, Winker hit three home runs in a narrow 8–7 victory against the St. Louis Cardinals, helping the Reds complete a four-game sweep with his second three-homer game of the year.

[26] On March 14, 2022, the Reds traded Winker and Eugenio Suárez to the Seattle Mariners in exchange for Justin Dunn, Jake Fraley, Brandon Williamson,[27] and a player to be named later, which turned out to be Connor Phillips.

Winker was later seen arguing with Angels interim manager Phil Nevin shortly before another skirmish broke out near them.

[33] Upon leaving the field, Winker flipped off the Angel Stadium crowd sitting behind the visitors' dugout, a gesture for which he later apologized.

Asked why Winker wasn't with the team during an American League Division Series, Divish said: I think he was home....

[39]On December 2, 2022, the Mariners traded Winker and Abraham Toro to the Milwaukee Brewers for Kolten Wong.

On July 28, 2024, the Nationals traded Winker to the New York Mets in exchange for minor league pitcher Tyler Stuart.

[47] On October 8 in the 2024 National League Division Series against the Philadelphia Phillies, Winker hit his first career postseason home run, a solo blast to right field off of pitcher Aaron Nola.