When you look at “what if” scenarios in sports, it’s typically about wondering what team or player among the elite of a sport’s history is the best of that exclusive group. What Super Bowl winner is the best? What NBA legend would win a one-on-one tournament? Could Hall of Fame pitcher X strike out Hall of Fame batter Y?
On a purely Yankees level, the best argument is probably which team is better between the 1927 and 1998 squads. Both won a World Series title after historic regular seasons, and are in the conversation for best teams in all of baseball history.