> On 25 Sep 2021, at 21:45, Thangalin via ntg-context <ntg-context@ntg.nl> 
> wrote:
> 
> 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?
> 

Not really generic, and maybe not what you want, but there is this:

\chapter{Eleanor Roosevelt}
\setupinitial[text={"G}]
reat minds discuss ideas; average minds discuss events; small minds
discuss people.

—
Bruce Horrocks
Hampshire, UK

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