I'll go legit. 
Batman: Penguin Triumphant is a one-shot with a cover date of July, 1992.
Synopsis for "Penguin Triumphant"
Inspired by a recent talk-show, the Penguin reinvents himself as a white-collar criminal, masquerading as a reformed businessman while actually using a new invention to manipulate Wall Street computers. To fully exploit these manipulations, he colludes with Randall Holmes, a childhood rival who has grown into one of Gotham's most powerful financiers; though Holmes still detests his heavy-handed "partner", his greed spurs him to honor the partnership until he can secure Penguin's methods for himself.
Within weeks, Penguin and Holmes sweep record profits on the stock market - a development that Batman closely monitors, especially as Penguin begins entering Bruce Wayne's social circles. Eventually, the Penguin attends a charity ball at Wayne Manor, where he develops a jealous fixation with Bruce. Hoping to distract and eventually trap Penguin, Bruce agrees - much to Alfred's horror - to sell Penguin the manor.
Meanwhile, Holmes' own investigation of Penguin encounters Bethany Wilcox, a ruthless social-climber whom Penguin had humiliated in high school. As part of her own vendetta, Bethany agrees to help Holmes unearth Penguin's methods, unaware that Penguin is beginning to tire of "legitimate" life and taking deliberate steps to expose his own operation. In time, his secrets are deduced by both Holmes and Batman; the police, meanwhile, receive a full confession as part of a state's-evidence deal against Holmes.
True to Penguin's predictions, Holmes almost immediately sends an assassin to eliminate any and all loose ends. When Batman intervenes, the situation becomes a three-way brawl, which Penguin narrowly escapes - but not without sustaining a bullet to the shoulder. As the wound overtakes him, he finds himself cornered by Bethany, who threatens to finish Holmes' assignment, but changes her mind when he encourages her, likening her spite and ego to his own.
Soon after, both the Penguin and Holmes are convicted of insider trading, and Wayne Manor returns to its proper owner.
Appearing in "Penguin Triumphant"
Featured Characters:
Supporting Characters:
Antagonists:
- Penguin
- Randall Holmes
- Cale
Other Characters:
- Mulroney
- Dr. Sterling
- Bethany Wilcox
Locations:
- Gotham City
- Argus Financial Center
- Wayne Manor
Items:
Vehicles:
Notes
- A Prestige-format graphic novel released, alongside Catwoman: Defiant, to coincide with the film Batman Returns.
- This one-shot is reprinted in Batman Arkham: Penguin.
Trivia
- Real-life white-collar criminals Robert Milken and Ivan Boesky are mentioned as inspirations for Penguin's plan.
See Also
Recommended Reading
- Batman Recommended Reading
- Batman (Volume 1)
- Batman (Volume 2)
- Batman (Volume 3)
- Batman and Robin (Volume 1)
- Batman and Robin (Volume 2)
- Batman and Robin (Volume 3)
- Batman Confidential (Volume 1)
- Batman: Gotham Knights (Volume 1)
- Batman: Legends of the Dark Knight (Volume 1)
- Batman: Shadow of the Bat (Volume 1)
- Batman: Streets of Gotham (Volume 1)
- Batman Incorporated (Volume 1)
- Batman Incorporated (Volume 2)
- Batman/Superman (Volume 1)
- Batman/Superman (Volume 2)
- Batman/Superman: World's Finest (Volume 1)
- Batman: The Dark Knight (Volume 1)
- Batman: The Dark Knight (Volume 2)
- The Brave and the Bold (Volume 1)
- Detective Comics (Volume 1)
- Detective Comics (Volume 2)
- Superman/Batman (Volume 1)
- World's Finest (Volume 1)