The next observed an act of trained birds and seized on the idea to use birds in his crime, a theme for which he became well-know.   He employed eagles, parrots, penguins and an ostrich before Batman cornered him and he escaped using his other old trick - an umbrella (Detective Comics #67).  In October of 1942, the Penguin devised a scheme to leverage his reputation by offering to plan crimes for a percentage.  In some cases, the percentage was 100% and the Penguin murders his client.  Batman thwarts the plan by setting up a counter-operation, luring The Penguin into contacting them and revealing his location.   While the Penguin deployed an arsenal of modified umbrellas, he was ultimately overcome and finally captured for the police (Batman #14).

The Penguin eventually escapes and seeing a talk by the warden at Gotham Penitentiary on famous criminals, Enraged at not being included, he launched a new career using sportsman themes but is thwarted again by Batman, this time using umbrellas (Batman #17).  By the point, the Penguin had settled into a life of crime centered on salving his ego and proving himself the better of Batman.  In the Fall of 1944, the Penguin and the Joker ended up in the same cell.  The two dueling egos determined that Gotham was not big enough for their two criminal aspirations and resolved that each would attempt to steal the Van Landorfe emerald, the loser leaving town.  Their efforts brought them into conflict with Batman and Robin and while the two temporarily worked together to fend off the heroes, they were both captured and swore to never work together again.  As far as is known, they never did (Batman #25).

The Penguin remained a thorn in the Batman's side for most of the next decade. While his early crimes were more onerous, he may have escaped the final penalty by being a different kind of bird, a stool pigeon, as when he ratted out "Squeeze" Miller leading to the latter's execution (Batman #56).  He was also notoriously vain, driven to criminal rage by perceived slights to his character or abilities.  He allowed himself to be captured when a book written about his crimes caught his fancy (Batman #27).  An effor to go legit was thwarted when a cartoon insulting penguins threw him into a rage. And when the Joker and the Catwoman were getting much more press, he went on a crime spree to make headlines until Batman put him back in prison (Batman #43).  In a final example, when he was mocked by the Birdlovers Society for advocating for penguins, he avenged his indignity by robbing them all blind (Batman #58).

However the most recurring feature of his crimes is his obsession with birds.  He once apprenticed with a famous ornithologist to use his aviary as a base of crime (Detective Comics #120).  He operated a bird shop as a way to get into homes of wealth customers (Batman #41).  He once created supposedly mythical birds as a part of a fraud racket (Batman #76) and even when he swore off birds, he somehow ended up getting them involved in his crimes and revealing himself (Batman #48). Criminals knew this and even mocked him his birthday by sending him avian reminders of his failed crimes (World's Finest #55), 

The Penguins last recorded encounter with Batman and Robin occurred in 1953. The later activities of the Penguin, whether he lived into the 21st century and whether he inspired a criminal legacy are all unknown.