He donned a silicon mask, wig, pink shit and even a bra.
He was very close to getting away with it, but officials say his nervousness gave him away as he tried to leave the prison in the western part of Rio de Janeiro, Brazil.
He planned to leave his 19-year-old daughter inside the prison while he escaped. Po-po are investigating her role as a possible accomplice.
Rio's State Secretary of Prison Administration released video footage of da Silva, in which he can be seen removing the mask and some of the clothes and saying his full name.
Authorities said da Silva was part of the leadership of the Red Command, one of the most powerful criminal groups in Brazil that controlled drug trafficking in a large part of Rio.
After the failed escape, da Silva was transferred to a maximum-security prison and will face disciplinary sanctions.