With the town already preparing to execute "Tennessee Kid" Cooper, Bentley concluded that the only way they would be able to break him out of prison in time was to do so from the inside. This meant that Sly would have to, for the first time in his thieving career, get captured. However, he needed to increase his criminal reputation to "outlaw" status first, otherwise he would be placed with all the minor lawbreakers rather than with Tennessee.
Given Toothpick's large ego, Sly's first act of crime was defacing all posters of the sheriff that were around the town. When that was done, Toothpick saw the vandalized posters and became enraged at Sly, deeming him a "troublemaker". Sly officially became a criminal after he stole Toothpick's Cuban cigar lollipop, an act that Toothpick also found out about. As the final crime to light Toothpick's fuse and become an outlaw, Sly tore down the banner advertising Toothpick's self-held festival in his own honor. He was finally noticed by the sheriff and apprehended.