The nine-year stretch from 1907 to 1915 is arguably the worst period in Yankees’ franchise history. The “best” they fared in that time was a second-place finish in 1910, but even then, they finished 14.5 games back of first. In every other season in that time, they finished more than 20 games back of first. The worst was the 1912 Highlanders team, who finished last in the AL with a 50-102 record, 55 games back of first. By multiple measures, that is the worst season in franchise history.
They might’ve been able to do a bit better if they didn’t make decisions like having a future World Series winning first baseman only pitch.