While there are some solid comedic beats in the script that show the writer has promise, they're too few and far between for a half hour television pilot.
It's also very unclear what the premise is that's going to fuel the comedy in this show. The script establishes that Carl is and was a jerk. Is he going to use his winnings to torment people? Spend it all trying to get his wife back through extremely elaborate means? Start a whole new life? A homeless jerk wins the lottery and...? There's a significant blank that needs filling in. It's difficult to even imagine what a second or third episode would entail.
Carl as a character is also problematic. He's a bad guy, and we see no redeeming qualities. He cheats on his wife, yells at his employees and is prone to outbursts of violence. We don't feel bad for Carl, it's the exact opposite. He's getting what he deserves. He's not a lovable jerk or a charming jerk, he's just a jerk. Carl has to be relatable and have *some* redeeming quality that makes the audience want to cheer for him and keep watching. Everything that happened was his own fault because, again, he's a bad guy. It's hard to figure out where the comedy is going to come from with Carl as the centerpiece. The script gives the sense that he's not going to do anything positive with his winnings.
I believe you can salvage the idea if Stephanie is the focal point. Restructure the script so that Stephanie is the only character he was *good* to and he treated everyone else like trash, leading to his predicament. Maybe his employees frame him for a series of crimes to get him out of their hair and Stephanie can't forgive him, leading to his homelessness when he gets out of jail. When he's homeless he learns the importance of being kind from a hobo camp he's in. Juxtapose the flashbacks of him being a jerk to other people with him being great to Stephanie. Then winning the lottery is his opportunity to win her back, through increasingly elaborate means while building his life back up and treating his fellow bums well.
The narrator is unnecessary, especially for a comedy. The flashback that starts on page 9 lasts until page 17, which amounts to 8 minutes of runtime. That feels extremely long to establish that Carl's a jerk and how he ended up where he is. Consider opening with Carl talking to Alfred, who should be a supporting character, in their hobo town explaining how it's his anniversary with Stephanie. Use the conversation to dip into flashbacks of Carl's poor behavior, then later that evening he gets drunk and visits her. That way we can empathize with Carl.
Too many scenes feel like they're reiterating things we already know. You really only need one scene to establish Carl is homeless and how he gets by and a couple of scenes to establish the type of person he was before he was homeless. The conflict that drives the story and the series could be/should be him getting his wife back. Winning the lottery is a means to that end. The dialogue is adequate, but feels like it needs punching up for more comedic beats.
