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Chapter 9

William Carter Sr.

Boston, March 1957

For years, William Carter Sr. toiled as an overnight janitor at a municipal building in City Hall Plaza. He began his shifts at 9:00 p.m., well after the offices had closed, since having a Black man scrubbing the floors would have been unseemly in the daylight. After two years, he was promoted and assigned to clean the mayor’s office, also at night. The mayoral staff spent longer hours in the office than he’d initially anticipated, so occasionally there were moments of awkward interaction.

His goal was to remain as invisible as possible and pass through the night with minimal disturbance. He was aware that the more recognizable he became to these people, the greater the threat that he might say or do something that could be interpreted as offensive and might put him out of work. It wasn’t uncommon for a Black civil service employee to disappear after complaints over behavior that included “too much chatter,” or “takes breaks that are too long,” or “general laziness,” or “delayed responses to questions.” He kept to silent, standard routines as much as possible to diminish his presence and therefore avoid conflict. This was a highly successful arrangement for William Sr., but one evening he was taken by surprise. The lights in an office were off, but someone remained seated at the desk.

When William Sr. went in to clean and change the trash, he flipped the light switch on and was jolted by the sight of a white man sitting perfectly still with closed eyes. John Sullivan, the deputy mayor.

“I’m sorry, sir. I didn’t know anyone was in here,” William Sr. said, his apology laced with fear.

“That’s quite all right,” the man said, rubbing his eyes. “I was in here just trying to pray on a solution to a problem. But please come in; I know you have to do your job. Don’t mind me.”

“Yes, sir,” William Sr. replied from the doorway before slowly stepping inside the office. He tried to sound happy, hoped his ebullience was clear.

Over the next two months, John Sullivan continued to work late but left his light on so that it was clear he was in there. When William Sr. came to clean, John sought out conversations with him, which of course made him uneasy. William did his best to appear unrattled and relaxed, as if this were the most normal thing in the world for the white deputy mayor of Boston to befriend a Black janitor.

One evening, John Sullivan, smiling and appearing evermore curious about his nocturnal companion, asked William Sr. about his ambitions.

“Well,” William Sr. said in a slow, drawn-out way to buy himself some time, “I’m fortunate to do this job right here.” He nodded.

“But what if you could do something else?” John Sullivan pressed.

“I’m not sure what else I could do, sir. I’ve been doing this since I first started working.”

“Okay, let me ask you this: Is there anything in life you want to accomplish?”

William fell quiet again and was unsure whether or not to reveal his aspiration to become a homeowner. He was sure John Sullivan, and all the Sullivans, for that matter, were already homeowners. He was reluctant to share something so personal and small with this person who had so much power.

“I’m looking to become a homeowner, sir,” William Sr. finally said since he couldn’t think of a believable lie.

“Is that so?” John smiled. “I hope you mean to do so here, in our fair city.”

“Yes, sir,” William Sr. replied and reached for the small trash can next to John Sullivan’s desk to give his nervous energy a productive direction.

“My eldest son is a student at The Galston School. Do you know anything about Galston?” John asked.

“No, sir,” William Sr. replied, scanning his knowledge for anything relating to a school named Galston. What he didn’t know at the time was that Galston was one of the oldest boarding schools in the greater Boston area, counting among its graduates the thirty-second president of the United States, Franklin Delano Roosevelt. William Sr. also didn’t know that in September 1951, three years before the landmark Supreme Court decision known as Brown v. Board of Education outlawed segregation in schools, Galston accepted its first Black male students. For some years, young Black men had been filtering through this elite boarding school, emerging ready to take on the top universities.

“They’re currently in the process of hiring for a groundskeeper for the campus,” John continued. “And because you have such an excellent work ethic, I thought you might be perfect for the position. It would be a much bigger job than you’re doing now, and you’d have a much bigger salary. And I’m sure your sons could also attend the school for free.”

William Sr. was surprised that John even remembered that he had sons based on their limited conversations. “That’s very generous, sir,” he said after a few seconds of stunned silence.

“I hope you’ll consider it. I would love to have you meet with the school next week.”

“Yes, sir,” William Sr. said.

The following Wednesday, William Sr. made the forty-eight-mile drive to The Galston School for his interview and, upon leaving the campus, secured a new job as the head of the groundskeeping department, where he would oversee a staff of twelve landscapers who now reported to him. William Sr.’s pleasant demeanor and a recommendation from the deputy mayor were all that were needed for the headmaster to offer him the position. The interview, a mere formality. In an instant, the 385 acres of this historic institution were under his domain. The headmaster also confirmed that as staff, William Sr. could have his youngest son, William Jr., attend Galston with tuition completely waived. Even though his first son, Walter Carter, wouldn’t be permitted to attend Galston because he was already midway through his high school education, William Sr. still felt especially energized about the opportunities that his namesake would have. He could never have predicted such a good fortune. Yes, it was as if he’d won the lottery. That smart, analytical boy of his, so damn lucky .