I don't know what any of that tells us, other than that the coins Mateo just lost seem to have been withdrawn from DB and redeposited without being used for anything in between.
Edit: I should point out that each of these transactions is a child of the one before it; they form a chain. Each (other than the first) has just one input, so you can follow the chain back from the last to the first.
The fact that the entire withdraw was untouched and sent back in its entirety should be a flag imho.
Flag for what? That he won 600 last time, withdrew them and then redeposited later on and lost it? :-) I don't want to defend them, they fucked up a lot of things, but some conspiracy theories are really funny.
What I mean is he went through the trouble to withdraw to 3 separate addresses, but then on a whim he decides to send it all back in 1 tx.