The Pirate pirate character to me means something like criminal + money + ocean, so we're ideally looking for words that will tie in more than one aspect of the character and/or meaning of the word (versus something else criminal like Bandit or Robber)
Pistol - Pirates are depicted using these all the time, seems very strong
Mint - Buried treasure is one of the most common pirate tropes and represents a figurative 'mint' to the finder. Pretty strong.
File - Piracy also, of course, has a meaning in computing, and is often called filesharing. Strong assuming Charriu thought of this angle.
Ninja - Another semi-fantastical character
Platypus - Australia -> Island ->Sea
Ambulance - I feel we as a group more often clue Ambulance, Hospital, etc. with associations to violence, which Pirate gets us
Day - I know there's a National Talk Like a Pirate Day. I don't know how popular it is. I feel like it isn't that popular, but if it's more popular or well known then Pirate Day ends up being a very direct connection
Lawyer - Stereotypically they steal money like pirates do
Roulette/Dice - These evoke the combo of money + elicit which Pirate also does, but they're pretty far off from the pirate trope
I feel good about Pistol + Mint + File but am a lot less certain about the fourth word
Pirates are usually pictured wielding PISTOLs and gambling with DICE, so I'm pretty certain about those. They probably preyed on COTTON shipments and MINTed coins/bars?
PISTOL = DICE > COTTON >>> MINT for me.
India, Platypus and New York could all have a very tenous connection.
Thinking some more on this, I'm pretty sure that the digital pirate is supposed to point to FILE.
Revised order: PISTOL = DICE = FILE > COTTON >>> MINT
PISTOL, DICE, and NINJA for the popular trope pirates vs. ninja were all strong to me and I kinda saw MINT as my number 4, now seeing the digital version comments, though, I'd move FILE in and go with PISTOL, DICE, NINJA, and FILE.
I feel pretty strongly about DICE, but for me NINJA is anti-clued by PIRATE. Would prefer MINT or COTTON as the last clue, but DAY or AMBULANCE would also work.
I wanted to give sunrise an opportunity to comment, but to keep this moving (and seeing that he's been online earlier today): POINT TO DICE
POINT TO MINT