After the Riddler gets out on parole, Batman and Robin find him and a couple of his minions making a late-night delivery of a big question-mark-bearing box. Believing that he's up to his old tricks, they swoop in to stop him — only for Charles Baxter, president of Wacko Toys, to intercede and explain that the Riddler is his new business partner and the box is a legitimate delivery of toy prototypes for a trade show.
Still suspicious, Bruce hears a news report about a theft of antiques from Newman's Import/Export Company. He concludes that the Riddler's statements that his criminal past was "ancient history" and that he was a "new man" were typical Riddler clues putting his signature on this crime. Dick has his doubts that Riddler would throw away his new respectability and wealth, but Bruce believes that he's simply too obsessed to change.
A commercial for the Riddler's new toy line contains an eight-digit number, which Batman initially interprets as map coordinates pointing to a bank. However, nothing happens there, and he realizes an alternative interpretation pointing to a street address where, sure enough, Ridder's minions are engaged in a robbery. Unfortunately, a display case falls and injures Robin, and the crooks get away.
Batman confronts the now respectable-seeming Edward Nygma at a party. Nygma mocks Batman as paranoid, transmitting their conversation to the party guests who laugh at the Caped Crusader. Unfazed, Batman warns Nygma that he'll be watching and will catch him sooner or later.
Privately, Nygma is rattled, and decides that there's only one thing to do — get rid of Batman once and for all....
- Bat Deduction: It's another Riddler episode after all.
- Berserk Button: Being called crazy is this for The Riddler.
- Bombproof Appliance: Batman hid in a safe. Even the Riddler couldn't figure this stunt out and was nearly driven insane by it.
- Call-Back: Charles Baxter was first mentioned in Riddler's last appearance as the designer of the puzzle the Riddler had hid his Virtual Reality machine in.
- The Cameo: The Joker and Two-Face can be seen in Arkham at the end of the episode, covering their ears to block out Riddler's ranting at how Batman could have survived his Death Trap.
- Chekhov's Gun: One of Riddler's toys, which is a two-way radio, eventually used against him in an Engineered Public Confession.
- Chronic Villainy: The Riddler sells his persona for a fortune and decides to abandon crime altogether in order to avoid risking his newfound wealth and freedom. However, because he has such a compulsion, he reasons that the only way he can do so is to kill Batman. Naturally, he fails, gets found out and arrested.
- Cut Lex Luthor a Check: Riddler has sold the license to his persona to a toy developer for a completely legal fortune. However, Batman is convinced that he will continue to commit riddle-crimes, even though it will jeopardize his freedom and financial well-being. When Robin wonders why he would take such a risk, Batman explains that for him it is not about the money, it is an obsession. As it turns out, Batman's right; Riddler is uneasy with his new life, and eventually decides to try to kill Batman once and for all just to remove the temptation to backslide.
- Cutting the Knot: Batman is locked in a showroom while a bomb goes off in 10 seconds. Riddler is stumped as to how he survived. Simple, he hid in a nearby reinforced safe.
- Engineered Public Confession: When Batman shows up alive and well, the Riddler desperately asks him to explain how he got out of the Death Trap, even offering to explain how he committed his own crimes and where he'd stashed the loot in exchange. Enter Commissioner Gordon and several GCPD officers, who were listening in; exit Riddler, now caught in clear violation of parole.
- Go Mad from the Revelation: Inverted when Batman survives the Riddler's death-trap, but will not tell him how he did it. The episode ends with Riddler ranting and raving as he tries to figure out how it was done.
- Insignia Rip-Off Ritual: The title card◊ (possibly a Shout-Out to an iconic page in page in Amazing Spider-Man #50) alludes to this with respect to the Riddler's iconic costume. In the episode itself he keeps wearing it even after "reforming", only shedding and burning the pieces once (he thinks) Batman is dead.
- L33t L1ng0: The Riddler uses a variation in one of his clues. The riddle number "31753701" from his toy commercial becomes "10LESLIE" when turned upside down.
- No Such Thing as Bad Publicity: Happens In-Universe when Batman and Robin reproach Charles Baxter for associating with a known criminal like the Riddler:Batman: Do you know who you're dealing with here, Baxter?Charles Baxter: Yes, a man who's going to make my company millions. Everyone's heard of the Riddler. You can't buy that kind of market recognition. Leave him alone, or I'll swear out a complaint against you for harassment!
- Riddle for the Ages: Played with. When Batman is able to escape The Riddler's deathtrap of sealing him in a building that has high explosives in it, the Riddler is so bewildered by Batman's escape that he no longer cares about going to Arkham or losing his now legitimate business and lifestyle and only cares about finding out how Batman was able to survive a trap he clearly shouldn't have been able to. While Bruce later explains it to Dick Grayson, and the audience, back at Wayne Manor, he never explains it to the Riddler himself. Mr. Nygma ends up going even more insane due to not getting an explanation.
- Unexplained Recovery: It isn't explained just how Nygma recovered from the comatose state he was left in from "What is Reality?"
- Villainous Breakdown: Riddler has one just because Batman will not tell him how he survived a seemingly perfect deathtrap.
- Worthy Opponent: Riddler knows he'll eventually backslide, but he feels he can outwit the cops indefinitely; it's Batman that he's worried about, calling him the only one who can challenge him and be worthy of the game. In the goodbye message, he even calls Batman exactly this.