Direct answer: Will Smith has won six consecutive World Series championships. Context and breakdown:
- The streak started with the Los Angeles Dodgers in 2020, followed by championship wins with three different teams in 2021–2023, and then continued with Dodgers titles in 2024 and 2025, giving him six straight World Series titles as a player named Will Smith. This makes him the only player to have won the World Series in six consecutive seasons under the same or different team affiliations as part of a single ongoing streak.
