He is first seen in "The Happy Wanderer" dealing for Tony Soprano's executive card game, and subsequently in "Amour Fou" dealing for Eugene Pontecorvo's poker game when it was robbed by Jackie Aprille Jr. and his crew. During the robbery, the players are shocked by what has transpired, but Sunshine simply remarks "Only thing we got here is practice", suggesting to the gunmen it was not even worth it to hold up the card game. Unknown to Sunshine, Gene Pontecorvo, or the others, the real reason for the robbery was a fruitless attempt for Jackie Jr. to prove himself as a gangster, mimicking a stunt Tony Soprano, Silvio Dante and his father did at a card game run by Feech La Manna years ago. Sunshine is reluctant to surrender his watch, only doing so when ordered by Christopher Moltisanti to cooperate with the thieves as they would likely get violent. Christopher's warning came true, albeit not over the watch. One of the gunmen then demanded Sunshine not to make eye contact with them, but when he noticed this was an unorganized nervous effort, Sunshine quotes one of his "old adages" akin to "victory has a thousand fathers but defeat is an orphan". In a moment of panic, one of the gunmen opens fire on Sunshine, mortally wounding him. This act leads to Carlo Renzi and eventually Dino Zerilli and Jackie Aprile, Jr's murder. When Ralph learns Jackie Junior masterminded the stickup, he is conferring with Tony Soprano about what to do. Both men regret that Sunshine is now dead, and his murder has escalated the gravity of the incident.