Between "Funeral for a Fiend" and "Wedding For Disaster".
Francesca Terwilliger stared blankly at the docks of Springfield as the boat moved farther and farther away. The sniffling of her sleeping little boy was the thing that made her snap out of it. Gino was curled up in his mother's lap, tears still streaming down his face from an earlier tantrum. Having grown attached to his grandparents and uncle during their brief stay in the same cell, he'd been reluctant to leave them. That was putting it lightly. Francesca wasn't sure where they would go once they were back in Italy; they probably weren't welcome in Salsiccia anymore. Still, it was better than 87 years in prison.
"Papa," Gino mumbled. "Vendetta."
Francesca ruffled the wild hair that he'd inherited from his father, and decided that the first thing she would do back in Italy would be to get her son a haircut. She didn't want any reminders of the husband who would rather kill a little boy than spend time with his own. She wasn't even going to cry for him. He wasn't worth it, and she had to be strong for Gino. Gino was the future, and Roberto was the past.
Unlike Bob, Francesca could let go of the past.
Well away from the penitentiary, Sideshow Bob stopped to rest. Escaping had been too easy; he'd been planning it from the moment his head cleared and he was freed from the straitjacket. He'd found the cell empty, save for himself, and was greeted with the news that his mother had been released, his father and brother transferred, and his wife and son deported. His family had apparently begged to get away from him and his unbearable, mad laughter.
This had hardly been the first time that Bob had been betrayed or abandoned like this. His own brother had tried to murder him, and then asked to be confined elsewhere when sharing a cell with Bob proved too much for him. Bob's parents had broken off most contact with him after his first arrest, claiming to be deeply ashamed of him, but Robert Senior and Dame Judith were far from saintly themselves. Bob had in fact blackmailed them into going along with the funeral plot. Not only had his mother been unscrupulous in getting many of her acting jobs, but his father had done some shady things that might have threatened his reputation as a respected doctor.
Sighing, Bob took out something from his pocket: a message from Francesca, written in Italian, about how by the time he read it, she and Gino would be back in Italy, and that he shouldn't bother to look for them if he ever escaped or was paroled, because pursuit of the vendetta came close to ruining Gino's future. His wife had also written a few other things that were unfit to be translated. To make sure that Bob understood her, Francesca had written her farewell letter on a photograph of them at their wedding.
A few tears splashed onto the defiled picture, and then a steadier watery stream that made the ink smudge and wreck what was left of it. So much for their wedding vows. The woman had a lot of nerve for blaming him for destroying their relationship. He'd been willing to give up pursuing the Simpsons, but no, she'd insisted that he go through with his vendetta!
With a soft growl, Bob crumpled the ruined photograph and wiped his tears away. He didn't need them! He didn't need any of his so-called family. No more tears would be shed for them, not ever.