
Jessica Jackson
Chicago-based activist with the group Chicago Flips Red, a longtime South Shore resident who speaks out against Chicago's Democratic political machine.
2
APPEARANCES
2
PODCASTS
012
DEC 30
JAN 6
JAN 13
JAN 20
JAN 27
FEB 3
FEB 10
FEB 17
FEB 24
MAR 3
MAR 10
MAR 17
MAR 24
MAR 31
APR 7
APR 14
APR 21
APR 28
MAY 5
MAY 12
MAY 19
MAY 26
JUN 2
JUN 9
JUN 16
JUN 23
JUN 30
JUL 7
JUL 14
JUL 21
JUL 28
AUG 4
AUG 11
AUG 18
AUG 25
SEP 1
SEP 8
SEP 15
SEP 22
SEP 29
OCT 6
OCT 13
OCT 20
OCT 27
NOV 3
NOV 10
NOV 17
NOV 24
DEC 1
DEC 8
DEC 15
DEC 22
DEC 29
JAN 5
JAN 12
JAN 19
JAN 26
FEB 2
FEB 9
FEB 16
FEB 23
MAR 2
MAR 9
MAR 16
MAR 23
MAR 30
APR 6
APR 13
APR 20
APR 27
MAY 4
MAY 11
MAY 18
MAY 25
JUN 1
JUN 8
JUN 15
JUN 22
JUN 29
JUL 6
JUL 13
JUL 20
JUL 27
AUG 3
AUG 10
AUG 17
AUG 24
AUG 31
SEP 7
SEP 14
SEP 21
SEP 28
OCT 5
OCT 12
OCT 19
Sep 22, 2026
We Are Not Conservatives
54:09
54:15
54:24
54:31
54:44

Jessica JacksonGUEST
Well, I feel like definitely there's room for something different in American politics.

Jessica JacksonGUEST
And even here at the local politics, I've made it clear that the only candidates that's worth voting for is Danielle Carter and Christian Maxwell.

Jessica JacksonGUEST
They're the only candidates that's not coming with all these political ties, with all this political garbage.

Jessica JacksonGUEST
We're constantly being badgered about the fact that Danielle Carter is now raising a whole lot of money because money is what makes the politics move the way that they move in Chicago.

Jessica JacksonGUEST
We're suggesting the fact that they have us in this political headlock, in this local election, where they have stuffed the ballot, even the mayoral race, with a bunch of losers, a bunch of known criminals, a bunch of crooks, and to have us in a situation where we don't even have anybody that we can vote for, that you're forcing us to vote for these same losers.
5 MINS LATER
September 19, 2026 - LIVE ON LAKE MICHIGAN
52:03
A
51:48Afro EliteGUEST
The antiquated, bureaucratic sense of doing politics from the good old boys needs to end in order for Chicago to change.

Jessica JacksonGUEST
Chicago Flips Red made the ground fertile for the Republican Party to come in.
9 MINS LATER