"Close Before Striking: Act 1"Edit
When Batman comes to the low-life bar The Ales of Justice looking for information on armour-piercing bullets that are being imported to Gotham, Matches Malone is the only person there who stands up to him, even spitting in his face. Previously he had a reputation for possibly being a stool-pigeon, but this act earns him an audience with Scarface, who recruits him to his gang.
Of course, Malone is really another of Batman's identities (Nightwing disguised himself as Batman to flush Scarface out) and armed with the information given to Malone, Batman is able to halt the shipment of bullets. However, this means that Scarface wants Matches Malone dead. Later, Oracle contacts Batman and Nightwing with the disturbing news that Matches Malone has been shot.