At a 2018 Chicago Board of Education
meeting addressing revelations of rampant
sexual assault and abuse of studentsSEPTEMBER 2019 | CHICAGO 93
shared a two-bedroom apartment in
Auburn Gresham, and she remembers
the moment. She also remembers watch-
ing Sweet Valley High on TV as a teenager,
marveling at the differences between
the fictional school and the one she
attended, Hyde Park Career Academy
(now Hyde Park Academy). Where was
the leafy campus? The comfy-looking
library? The pristine classroom? “I got a
good education, but I always felt like my
schooling was less than what it should
have been,” she says.
We are seated in Jackson’s corner
office at CPS headquarters downtown.
The room is light and airy, with white
walls and a wide bank of windows.
Dressed in a floaty white blouse, paisley
pants, and a Zara belt, Jackson had got-
ten up from her desk when I was shown
in and invited me to join her at a small
round table. The drink of the day is water.
Once our conversation gets underway,
I’m surprised to note a total absence of
interruptions — no knocks on the door
from aides, no apologies for having to
take a call or return a text. Jackson exudes
an air of control and calm precision. She
speaks in paragraphs. Her knowledge is
deep and extends well beyond public edu-
cation. She maintains eye contact as she
talks, breaking her gaze only to stare into
the middle distance as she’s finishing a
particularly complex thought.
When at one point I cast my eyes
across the smattering of family photosand awards behind her desk, the room’s
only personal touches to speak of,
Jackson admits she hasn’t had time
to make the office her own. “I did not
pick this green carpet, and I did not
paint that accent wall yellow,” she says.
Admittedly, she’s been busy. “This
hasn’t been a honeymoon.”
Indeed, Jackson has inherited major
problems: declining enrollment, schools
that are drastically over- or underpopu-
lated, the Illinois State Board of Education
imposing a monitor on the district’s spe-
cial education program after finding that
CPS had delayed and denied some ser-
vices to students, plus an investigative
report by the Chicago Tribune that showed
CPS had mishandled sexual abuse cases
for over a decade. What’s more, her twopredecessors left under a cloud of scan-
dal — one of them is in federal prison for
taking kickbacks. Jackson is the district’s
seventh CEO in 10 years.
She is also one the first in decades who
is an educator. Jackson started teaching
social studies at South Shore High School
in 1999, while earning a master’s in edu-
cation at Chicago State University. “At the
time, South Shore was one of the lowest-
performing schools in the state.” Jackson
remembers stuffing student papers in her
backpack to grade at home and being told
by a not her teacher to for get it — t hat i f she
couldn’t get something done during work
hours, not to bother.
It was as if William Bennett’s assess-
ment had become self-fulfilling. “I didn’t
like these approaches that said, ‘The kids
live poverty so we shouldn’t have stan-
dards.’ Until then, I hadn’t realized that
so many black people were having a dif-
ferent experience in education than I had
had. I started feeling I should be in CPS
[leadership], that I had gifts and the cour-
age to try to do something.”
In 2003, when she was just 26, she
helped secure a $500,000 grant from
the Bill & Melinda Gates Foundation to
underwrite the opening of Al Raby High
School in East Garfield Park. Occupying a
closed CPS building that had once housed
a girls’ high school, the new school
focused on intensive support for a small
group of fewer than 400 students, with
a n empha sis on science, tech nolog y, a nd
the environment. The school was next
to the Garfield Park Conservatory, and
Jackson was able to create a partnership
with it on various projects. The following
year, Jackson was made principal. “At the
time,” she says, “the area had the highest
murder rate in the city. But those kids in
t hat school ach ieved so much bec ause t he
teachers there believed they could and
we told them they could.”
By then, Jackson was already enrolled
at the University of Illinois at Chicago,
where she’d just earned another mas-PHOTOGRAPH: BRIAN CASSELLA/ ter’s and would go on to earn a doctorate,
CHICAGO TRIBUNE
Public
Schools
2019“I wake up in the
middle of the night
thinking about them,”
Jackson says of the
sexual misconduct
reports that
shook CPS.