signing under such a man

Hi everyone, please, from Peter Pan:

"Now then, bullies," he said briskly, "six of you walk the plank to-night, but I have room for two cabin boys. Which of you is it to be?"

"Don't irritate him unnecessarily," had been Wendy's instructions in the hold; so Tootles stepped forward politely. Tootles hated the idea of signing under such a man, but an instinct told him that it would be prudent to lay the responsibility on an absent person;

The kids are prisoners and Tootles later says to Hook that his mom wouldn't like it if he becomes a pirate. Please, what does signing under mean?

Thanks!

Here it means to engage himself under the command of Hook. He is volunteering to be a member of Hook’s crew. It was traditional for sailors to sign a document expressing their engagement as a member of a ship’s crew, military service, etc.

Yes, in the 21st century we might say "signing up to serve under such a man". For all I know, the version of #1 may be genuine naval/pirate jargon for that time!

Gabriel Aparta said:

Please, what does signing under mean?

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That you're dividing the sentence incorrectly. It's "[signing] [under such a man]", not "[signing under] [such a man]".

The verb in current use is not "to sign" but "to sign on": sign on - WordReference.com Dictionary of English

Collins Concise English Dictionary © HarperCollins Publishers::
sign on vb (adverb)
(transitive) to hire or employ
(intransitive) to commit oneself to a job, activity, etc
(intransitive) Brit to register as unemployed

Under = under the command of

It was common for crew members in the Merchant Marine and Navy during the 18th and 19th centuries to sign a contract agreeing to terms, and likewise those who wanted to join a pirate crew had to agree formally to the ship's "articles" regarding division of plunder, compensation for injury, punishment for infractions such as fighting with another crew member or injuring another crew member, and voting rights. That formal agreement often involved them signing their signature, or if they did not know how to write, making their mark, on a document.

blint said:

It was common for crew members in the Merchant Marine and Navy during the 18th and 19th centuries

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To sign on is still the common term for joining a vessel as a member of the crew. You name is, as you say, entered into the ship's articles.

PaulQ said:

(intransitive) Brit to register as unemployed

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Yes, in my experience you sign on every two weeks to claim unemployment benefit and you sign up for a period of military service or a comparable commitment. Though I have not done the first for decades - the procedure is probably different now!