Sawyer is accused of stealing Shannon Rutherford's (Maggie Grace) inhaler, and Sayid Jarrah (Naveen Andrews) tortures him in an attempt to find out where it is.

As he rushes to leave, his briefcase falls open, revealing thousands of dollars in cash he claims she was not supposed to have seen.

Later, Sawyer is revealed to be a con artist in debt with a loan shark, Kilo (Billy Mayo), who demands his money back, plus fifty percent, by the next day.

Sawyer goes to Jessica's house to finalize the deal, but reconsiders upon seeing a small boy (Jim Woitas), their son, emerge from another room.

On the beach, Sawyer catches Boone Carlyle (Ian Somerhalder) searching through his stash of items he salvaged from the crash, and Jack Shephard (Matthew Fox) attends to Sayid's head wound.

Meanwhile, Shannon begins to have trouble breathing due to her lack of medication and panic resulting from this problem.

Kate elbows Sawyer, and an enraged Sayid attacks him, stabbing him in the arm and hitting an artery.

Despite pleas from Kate, Sayid sets off to explore the island's shoreline in self-imposed isolation, needing time to come to terms with his actions in torturing Sawyer, while Sun-Hwa Kwon (Yunjin Kim) helps Shannon by making a eucalyptus salve to clear her bronchial passages.

The episode also shows the moral ambiguity of some characters by revealing more of their personalities, with the ones introduced as protagonists doing things that are generally not viewed as protagonist-like– an example being Jack beating Sawyer and eventually asking Sayid to torture him; and an antagonistic character, Sawyer, proving not to be solely antagonist-like– an example being his backstory and flashback, which show that he is not exclusively evil.

"[2] Sawyer and Jin-Soo Kwon (Daniel Dae Kim) were the least-liked characters by viewers during the first few episodes, because, according to Lindelof, "they were just really obnoxious, bad guys".

Chris Carabott of IGN gave the episode an 8.4/10 and called it "a well-written, fascinating character piece that does an excellent job of bringing Sawyer into the spotlight", later praising Josh Holloway's performance, writing that "The success of this episode begins and ends with Josh Holloway.

So far, we know that he's good at playing Sawyer: The Tough Guy, but now he has to sell a multilayered fragment of a human being who hates himself for becoming the man who destroyed his family.

Club gave "Confidence Man" a B and wrote that "Sawyer’s flashback is really well done", but adds that "Lost—at least at this point in its run—is not calibrated for one of its characters to torture another one.

The episode simply doesn’t do enough to get us to the point where we can understand why this event was necessary, and why cooler heads couldn’t have prevailed.