Signed in the summer of 2023 in what was then the largest transfer involving a USL player, the Louisville-born centre-back arrived at Benfica having come through the academy of his hometown club, Louisville City FC.

Wynder joined the LouCity academy at its founding in 2020, signed a USL Academy contract in February 2021 and turned professional four months later, going on to make more than 40 first-team appearances and score twice before his move to Portugal.

At Benfica he was integrated into the B team in Liga Portugal 2, where he continued his development as a tall, left-footed central defender, scoring four goals across two seasons. He was promoted to the senior squad and made his first-team debut in April 2025 in the Taça de Portugal, wearing the number 66 shirt.

Internationally, Wynder has represented the United States at U17, U19 and U20 level, featuring four times at the 2023 FIFA U-20 World Cup, where the Americans reached the quarter-finals.