So he's been to thailand and most likely got his tatoo's there, which means he went after his wife left him, because the lack of a tattoo in those flashbacks. He learned poker theire. Hmm maybe it was a getaway after his wife left him or maybe he went for the same reason he went to Sidney, to pick up his dad.
"Dad? Is that you? It's me Walt. You're not still on the island, are you? Those nice guys in the boat took me home? If you've been sitting at a computer, why haven't you returned my email? Dad?"
Oh look, there's my favorite leaf!
Sawyer: Shot??!! We don't even get a warning??
Pickett: Shocked. I said shocked.
Shocked Shocked Shocked Shocked Shocked Shocked
Maybe Jack has a real crazy side - tattoos, hookers, drugs...
"Dad? Is that you? It's me Walt. You're not still on the island, are you? Those nice guys in the boat took me home? If you've been sitting at a computer, why haven't you returned my email? Dad?"
Oh look, there's my favorite leaf!
Sawyer: Shot??!! We don't even get a warning??
Pickett: Shocked. I said shocked.
Shocked Shocked Shocked Shocked Shocked Shocked