The Rogers Family

Three years ago, the Roxbury couple left the school system dismayed after their first-born son, Jaiyere, did not get into any of their seven choices. Instead, they enrolled him in parochial school, where he is now in the first grade.

The Rogers are hoping the lottery will bring better news for their other son, Chief Jasaad, who will turn 4 in June.

"If I don't give the school a B+ then he won't go,'' said Jeff Rogers. “I can't afford to put him in a parochial school, but maybe I'll just do that. ... We are not going to move out of Roxbury, even if we could. But I'm going to find a way to get him into a good school.''

Rogers, 29, is a senior family partner at Children Services of Roxbury, which helps disadvantaged children and their families. Kimesha, also 29, is a district manager at the retail company Expressions who sometimes log 15-hour days. The couple, who grew up attending Boston public schools, live in a spacious, neat single family on a dead-end street.

Frustrated that Jaiyere didn't get any of his picks, Kimesha Janey-Rogers turned over this year's school decisions to her husband, who is anxious to find out where the school district will send his little boy.

"I remember opening up the letter [from BPS] and thought 'We can live if we get our third choice,' '' recalled Kimesha Janey-Rogers of her disappointment three years ago. "I thought, 'How bad can we do?' ''

Now, Jeff Rogers has kept his choices to just three schools, all in Roxbury. He would love if Chief attends a school that doesn't have too many student behavioral issues and one where children are expected to excel instead of simply getting by. But, he said, he's facing reality.

Rogers is an advocate of Roxbury who grew up near there, attended schools there, and lives, loves, and works there. Deciding where to send Chief runs contrary to his passion for his neighborhood. But when it comes to their sons, he and his wife are prepared to tighten their budget even more to send Chief to join Jaiyere at Our Lady of Perpetual Help in Mission Hill. And they are considering charter schools.

"For me it’s a little bit of unrepentant hypocrisy,'' Jeff Rogers said. "I know I want the Boston Public Schools to be strong and my pride in Roxbury is very high. But if you say, 'Jeff, can we take your kids and put them in a random school in Roxbury?' I'd have to say 'no thanks.' "