"Dole out the beatings" & "a pinky back into this pond"

Question

John Wick: Hello, Winston.

Winston: Jonathan. Now, as I recall... weren't you the one tasked to dole out the beatings, not receive them?

John Wick: Rusty, I guess.

Winston: To what do we owe the pleasure?

John Wick: Iosef Tarasov.

Winston: What about him?

John Wick: I'd like to talk with him.

Winston: A talk, you say. I'm familiar with the parlance, Jonathan. I want to ask you this. Have you returned to the fold?

John Wick: Just visiting.

Winston: Have you thought this through? I mean, chewed down to the bone? You got out once. You dip so much as a pinky back into this pond... you may well find something reaches out... and drags you back into its depths.

The dialogue above is excerpted from the movie John Wick. The scene happens when Wick goes down to the secret club and talks with Winston, owner of the Continental Hotel, who also runs a hitman organization under the table.

I don't quite grasp the meaning of the two bold sentences.

I take the first to mean punishing the opponents while not taking too much hit, but I don't know what the beatings refer to.

The second sounds non-standard to me, though I understand Winston is trying to warn Wick about the seriousness and dangers of this issue. What is "a pinky back into this pond", a turn of phrase? Besides, I would say it this way, "You dip so much like a pinky back into this pond". I don't see the usage of "as" here. Please help to clarify this.

Answer 1

They're both very colloquial - as you probably guessed…

dole out the beatings, not receive them

Bearing in mind he's some kind of supposedly-retired tough guy, visiting his old boss, if I recall correctly, his 'job' would normally be to damage people for a living. To dole out is 'to give', rather informally, to usually more than one recipient. It has a hint of 'giving by the rich to the poor'. It's also used in the UK as an informal name for Social Security/Welfare payments, 'the dole', implying a meagre hand-out to all who need it.
The beatings, I presume, is rather more obvious - something more than a punch in the nose.

So overall, he's surprised at the apparent bruising John Wick has. He would always expect the other guy to have the bruises.

dip so much as a pinky back into this pond

This one is simpler.
It's a slightly mixed metaphor though, so I'll break it down...

A 'pinky' would normally just be a colloquial term for your littlest finger.
To 'dip your toe in the pool/pond' would be to 'test out the water' putting the smallest part in to see if it's not too hot or cold.
Another colloquial term for toe would be 'piggy' [from the nursery rhyme, This little piggy went to market…]

So much as is a fairly standard, though probably archaic, term. It could be replaced by 'as much as' or 'even as much as' but not by 'so much like'. Think of it as being more 'the smallest amount possible, or even less'.
In this context it means 'don't do it at all, not even one toe/finger'

So he's just mixing the two metaphors pinky/pond rather than piggy/toe/pond.
He's implying that if John was even to think about returning to his old life, it may just drag him back into that life more than he would wish.
He's using 'reach out' & 'depths' at the end to reinforce the water analogy, implying there may be metaphorical crocodiles or sharks in the water/his old job.