Sometime after "Stranger in a Strange Land" (3.09) and before "The Man from Tallahassee" (3.13) – presumably this is what Jack is doing while Kate, Sayid, and Locke are trying to find him at the Barracks. Maybe Locke is playing chess with the computer at the same time...
Background
Jack has made his deal with Ben, saved Sawyer and Kate, and successfully completed Ben's surgery. He has also, after treating Ben's infection, successfully negotiated Juliet's freedom by forcing Ben to commute her death sentence. All of the Others (with Jack and Juliet) have left "Alcatraz" island and the Hydra station so that Kate/Sawyer can't come back to find them. They are now at the Barracks.
Recap
Jack and Ben are playing a game of chess in Ben's living room. The game has been going on for a little while and each player has lost a few pieces. Ben is in a wheelchair. Jack is bent over the table, leaning on his right hand, concentrating hard on his next move. However, Ben is sitting upright, looking occasionally at the board but mostly at Jack. He seems very confident – as always. He knows more (about chess but more importantly about the island) and is pleased to have the upper hand. The contrast between the two is blatant.
Their conversation is very telling, but I don't want to completely quote it word for word here. Ben suggests that it must be strange for Jack. Jack first comments that it's not strange, because his dad taught him to play when he was a kid. Ben corrects this misunderstanding and says that he meant it must be strange for Jack to be with the Others. Jack seems pretty confident that he is in a good situation and will be leaving the island soon.
As their conversation continues, Ben asks if he might convince Jack to stay, while still claiming that he "intends" to honor their deal. This comment of course makes Jack suspicious. Ben promises the he won't do anything to prevent Jack from leaving. However, he continues, if the island doesn't want Jack to leave then it won't let him leave. (This distinction that Ben is making reminds me of him saying he didn't tell Michael to kill Ana-Lucia and Libby.) Jack thinks about this in concrete terms, asking if the island will sink the sub. Ben laughs this off, but then adds:
"But if you do leave this place, a day may come when you wanna return."
"Never."
"I've learned never to say never... and if that day does come, I hope you remember this conversation."
Ben then "castles" his king, thus thwarting Jack's attempt to win the game. Ben says, "It was a nice try, though," with smug satisfaction, while Jack looks at him with utter annoyance bordering on hatred.
Chess
I'm not very knowledgeable about chess, but I know a little bit and have researched a little more on Wikipedia because I'm sure the writers are trying to make a point with the game and the moves that Ben and Jack make.
First, of course, there's a general overall meaning in just playing chess. Ben leads people as if he were playing chess. He's always willing to sacrifice someone (think of poor Goodwin) for the betterment of the whole. He also prides himself on being able to manipulate situations, thus causing others to make moves he can take advantage of. (Just think of his relationship with Locke.) And, as he himself has said, he always has a plan. He makes predictions and strategizes, two important skills for any good chess player. On top of that, the writers obviously find importance in game play in general – we see Hurley, Sawyer, and Locke playing Risk on this very table in Ben's house in season four.
In this particular game, it's interesting that they are not playing with black and white pieces; instead, the set is made of stained wood, so the pieces are two shades of brown. There have been a few references to black and white in the series (i.e. backgammon and the rocks found with Adam and Eve), so it's interesting the writers didn't use them here. Nevertheless, Ben is playing the darker pieces.
Based on what I have read at Wikipedia, the player playing white is considered to have an advantage because they make the first move causing black to start from a defensive position. I'm sure Ben set it up as a generous offer to Jack, but it only makes his assumed victory sweeter. Ben also likes to have as much knowledge as possible of his opponents (think of all the files, the information gathering at the flame station, and his spy on the boat), which benefits him in most situations. Plus, Ben is often viewed as an evil character – no matter that he says he's a good guy – so black fits that as well. That's probably why the writers used the wood set, because in the end Jack and Ben are both shades of the same wood, neither is all good or all evil.
The only specific moves we see are Ben taking one of Jack's pawns with a pawn (so many of the Others and 815ers could symbolize these pawns, but Charlie seems to most fit the bill), Jack taking one of Ben's bishops (possibly Tom?) with his queen (Juliet or Kate could fit this bill), and then Ben castling his king (just like protecting the Others at the Temple or even trying to protect his daughter). I don't think that these metaphors are necessary but they do seem to fit.
Ben's moves are both quick and precise, whereas Jack spends a lot of time thinking about his move and, even after moving, continuing to stare at the board thinking/re-thinking all that he's done/will do. He's putting a lot of effort into trying to do everything perfectly, but not succeeding. Sound familiar?
Thoughts
I will not claim that everyone should watch each and every webisode, but I highly recommend this one. On top of the great acting by Michael Emerson, it's filled with so much foreshadowing – Locke sinks the sub, Ben/Jack continue their chess moves as Jack tries to get everyone off the island, Jack wants to get back to the island. And, since we know Jack is off the island, I guess that means the island really did want him to leave.
When this scene first aired, the audience already knew all of these things. But, in watching it again now, Ben's comments to Jack about him wanting to come back are even more profound – especially after having seen their conversation in the funeral parlor and Ben's sacrifice to move the island, thus never being able to return (supposedly). On top of that, if the island really did want Jack to leave, then why does it now want him back? Plus, after Hurley apparently played chess with Walking Dead Mr. Eko, I have to wonder if Ben has ever played a game with Jacob. Like the computer in the Flame Station being unbeatable, is that Ben's reputation among the Others? Also, with Jack's reference to his dad teaching him the game, I wonder about all of the other things Christian will have to teach him – whether on or off the island in the future – so Jack can ultimately win the game. I'm sure the metaphorical chess will continue all the way until the end – and I have no idea who's going to win that game or even what winning will necessarily mean, but I am looking forward to watching the game all the way to it's completion!
Random Info
I didn't mention this in my last review, but unfortunately you can no long watch these webisodes on ABC.com. The page is still there, but, at least for me, the episodes will not play. Thankfully, you can easily find them on YouTube. The one's I have been watching have Swedish subtitles, in case you need those...
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