46 THENEWYORKER,DECEMBER2, 2019
hears the nuances in what the other per-
son is saying”). They teach the volun-
teers how to obtain court documents in
order to learn the official narrative of
the crime. There are monthly meetings,
too, for which Lewin brings in speak-
ers who have served decades in prison.
L
ee, White, and Button studied Pa-
role Prep’s training materials and
took notes at its meetings. From their
first visit, they had only five months to
help Richard Lloyd Dennis—whom they
call Lloyd—prepare for his next parole
interview. Volunteers working with peo-
ple in prisons closer to New York City,
such as Sing Sing and Fishkill, were able
to visit often, but since Auburn was so
far away, they had to rely more on letters
and calls. In a letter to Dennis in March,
2018, a few months after they first visited
him, they wrote, “With your next parole
hearing quickly approaching, there is
much work to do, and an important part
of this work is the process of writing and
reflecting.” Parole Prep had distributed a
memo with writing prompts, and the vol-
unteers began including a few of them
in each letter they sent. At first, the ques-
tions were innocuous: “How would you
describe yourself as a young man?” “How
do you think you’ve changed since being
in prison?” But soon they became more
challenging: “What happened that night?”
“What do you remember of the victim?”
In his letters, Dennis began to tackle their
questions. “Temper is an attitude, a dis-
position and over the years I have learned
to control it,” he wrote. “I felt real bad
about my situation ... but you should
know that I felt real hurt inside also for
the officer and his family.”
Many people who have been in prison
for thirty or forty years lose contact with
their families, but, in an early letter, Den-
nis enclosed phone numbers for eight
relatives. One Saturday in February of
2018, the volunteers got together at a
coffee shop in Brooklyn to work on his
parole packet. Button called Dennis’s
sister, Velma, in Virginia. Velma, who
had been sending letters to the parole
board for years, asking for her brother
to be freed, was delighted to hear that
someone was trying to help him get out.
Dennis was the sixth of seven siblings
who had grown up in New Castle, Penn-
sylvania. After high school, he spent a
year in the Marine Corps, then moved
to New York City, where he got a job
as a cook at a nursing home in Queens.
Button asked Velma to write another
letter on his behalf, and she sent it the
following week. She wrote, “Richard has
been in prison almost forty-six years
now (he turned twenty-one in prison),
no previous criminal record, high school
graduate, employed prior to entering
the system, raised in a two parent home,
has four brothers and one sister (none
in the system), and all of us ready to
step in and help upon his release!”
By many standards, Dennis was a
strong candidate for parole. He’d had no
disciplinary infractions for several years;
he had a place to live, with Velma; and
he had lined up a job as a laborer with
a contracting company run by Velma’s
son-in-law. The volunteers made the
drive to Auburn in February and again
in April, 2018, when they conducted a
mock parole interview with Dennis in
the visiting room. They had studied the
transcripts of his last two interviews, and
had noticed that many of his answers
were very short. “Just saying yes or no
unfortunately paints a picture of some-
one who really doesn’t want to be there,”
White explained. They tried to teach
him a strategy that any good job inter-
viewee knows: the art of the pivot. White
told Dennis, “Even if they are asking yes-
or-no questions, take every opportunity
to be, like, ‘Yes, and ...’” He recom-
mended that Dennis then mention some-
thing positive, like the fact that he had
many relatives willing to take him in.
In May, two weeks before the parole
interview, White mailed copies of Den-
Dennis with a family photo taken at Comstock prison in the nineteen-seventies.
