Henri Menke provided a partial solution:
\defineinitial[two][method={first,auto}]
\setuphead[chapter][
after={\placeinitial[two]},
page=no,
]
\starttext
\chapter{Harriet Tubman}
"Every great dream begins with a dreamer. Always remember, you have within
you the strength, the patience, and the passion to reach for the stars to
change the world.
\chapter{Eleanor Roosevelt}
Great minds discuss ideas; average minds discuss events; small minds
discuss people.
\stoptext
However, the leading quotation mark is gobbled. Is there any generic way of
detecting a leading quotation mark while keeping initial caps on the first
character?
Thank you!
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