Will Jim Harbaugh win a Super Bowl with the Los Angeles Chargers before April 2029?
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There will be five Super Bowls between now and then that he can win: 2025, 2026, 2027, 2028, 2029. Resolves NO if he leaves the team, they win without him, or he wins with a different team.
Resolves YES if they move back to San Diego or something and win a Super Bowl with him as the coach ie the "Los Angeles" part is optional.
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