Executive producer Damon Lindelof suggested in this week's Official LOST Podcast that the title of this episode might have a double meaning. Specifically, he suggested "to con again" in addition to my first thought of "reconnaissance." Reconnaissance is, of course, scouting to gain information, which is what a confidence man like James Ford would need to do prior to an effective con. However, James is revealed to be a detective in the flash-sideways, whose undercover work includes using grifter techniques (like the "pigeon drop") to catch other con artists, hence the word "re-con."
The repeated theme of this episode is "trust." Most notably manifested in his partnership with Miles in the flash-sideways, and the deals he made with Charles Widmore and the Man in Black on the Island. This is a question inherent to James' nature, though it now seems that he has the choice to use the asset of trust for good or evil. He can gain a person's trust to catch a criminal, or to pit two foes against each other and rescue his friends.
In what has become traditional flash-sideways fashion, the trust issues between him and Miles are resolved by the end of the episode when James tells him the story about "Sawyer" and the death of his parents. Unlike on-Island James, he also reveals his hope that Miles will talk him out of killing the man who is responsible for the death of his parents. Because of this moral character in Det. James Ford, it is interesting to note that in the Island timeline it was Jacob's pen that allowed young James to write the letter to "Sawyer" ("The Incident"), which he eventually reads to Anthony Cooper before killing him ("The Brig"). It seems that Jacob caused James to go down the dark path, which seems inconsistent with a character who is supposedly good.
On the Island, James goes to Hydra Island at the request of the Man in Black to gain information about Widmore's people. James tells Widmore that he will march "Locke" to him, unaware, so that Widmore can kill him. James then tells the "Locke" what he told Widmore, and that he'll be surprised when they change their plans. What is interesting to me about this, given the "re-con" title, is that we do not know for certain that Widmore wants to kill the Man in Black. If Widmore is as evil as Ben Linus claims, then James is the one who was conned.
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