[3] On December 30, 2019, Kessler signed a Generation Adidas contract with Major League Soccer and entered the 2020 MLS SuperDraft.

[8] On August 3, 2024, Kessler was traded to St. Louis City SC, in exchange for Tim Parker plus $600,000 in General Allocation Money.

[10] Kessler was named to the final 20-player United States U23 roster for the 2020 CONCACAF Men's Olympic Qualifying Championship in March 2021.

[12] Kessler was added to the United States national team for the quarterfinal round of the 2021 Gold Cup, pending CONCACAF approval, replacing an injured Walker Zimmerman.

[13] Kessler was cap-tied to the United States by making his senior debut as an extra-time substitute to close out their 2021 CONCACAF Gold Cup Final victory over Mexico.