Mr. Cintron is in charge at Progress, and Reese seems to genuinely look up to him. "He was cool," Reese tells us; "He was the only one at Progress who I believed most of the time" (2.6). In general, Mr. Cintron is in Reese's corner, but he gets frustrated when Reese gets in fights. "Anderson, do you have to work on being stupid or does it just come naturally to you?" (5.28) he asks at one point. In case it's not obvious, Mr. Cintron doesn't mince words.
While he's realistic enough to know that many inmates won't be reachable, Mr. Cintron seems genuinely interested in the possibility of reforming both his kids and his facility. He wants to implement an individual tutoring program, but he knows it will never get funded. "I'm supposed to fly up to Albany tonight and plead the case tomorrow, but I know the legislature won't spend the money for it," he says. "They're not smart enough. I'll be back by the afternoon with the bad news" (4.44). And yet he goes anyway, fighting the good fight even if he knows it's for naught.
That said, Mr. Cintron is up against a lot of people who aren't progressive thinkers like him, and it's clearly starting to take a toll—there's a weariness about him. "They're going to look into my face and talk about recidivism rates and emotional instability and social understanding—but in their hearts they're going to keep it a lot simpler. They're going to be thinking that people like you don't deserve a chance" (6.41), he tells Reese. Ugh, right? But the important thing is that he thinks Reese deserves it, at least most of the time. It's enough to change Reese's life.