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Roosevelt and Churchill used an extremely sophisticated telephone encryption system, SIGSALY, to communicate during WWII. In fact, they did not use it all the time because apparently it changed the voices a lot.

At the time, teletypes with automatic encryption existed. They were much easier to build and handle than SIGSALY.

Wouldn't it have been an alternative to have a quick typist on both sides, so that Roosevelt and Churchill could communicate as in a modern-day online chat?

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During that period, both Churchill and Roosevelt were old men more used to hand written letters than "high technology" teletype writers.

Teletype writers are NOISY!

Using teletype writers can be a slow process & thus make a l-o-n-g conversation.

Telephones, despite sophisticated encryption technology, are immediate and more intimate. In addition to hearing what the other person is saying, much can be ascertained from tone of voice, pace of speech, pauses and delays of speech.

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    It is also impossible to overrate the importance of the personal relationship between Roosevelt and Churchill in the winning of the war.
    – Gort the Robot
    Aug 30, 2020 at 17:28
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    this holds true even today, if you consider how shortened smartphone messaging conversation is, how long it takes even with a keyboard to type a long statement and how prone to misunderstanding both still is. While text can be nice as a summary to agree upon, to discuss delicate complicated issues with nuances that need to be argued and cross-examined I'd always prefer something voice based compared to something typed - even given today's tech and the fact that I'm - compared to the average person - a relatively fast typist and experienced in typing longer texts.
    – Frank Hopkins
    Aug 30, 2020 at 19:40
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    And emojus and smilies weren't invented in WW2, so there was no way of knowing what mood they were in using typewriters.
    – bandybabboon
    Aug 31, 2020 at 8:24
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    indeed! could they even type?
    – Jasen
    Sep 1, 2020 at 9:39
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    @Jasen Churchill had worked as a journalist and was already a writer, so it's quite possible. But they wouldn't have needed to; they would have had plenty of skilled and trusted typists/teletype operators available anyway
    – Chris H
    Sep 1, 2020 at 14:59
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For a print work I recommend Francis L. Loewenheim, Harold D. Langley, & Manfred Jonas, Editors; Roosevelt and Churchill: Their Secret Wartime Correspondence, Dutton, 1975. Contains some 600 or so of the more than 1700 cable messages which passed between Roosevelt and Churchill from shortly after the start of the war in 1939 until April 1945.

Or if you really want to see something on the subject of Roosevelt-Churchill communications visit here at the FDR Library. Scroll down to the Series 1 messages and find the list of communiques October 1939 to April 1945 all available in digital format.

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