08/28/2026
Sylvester Whittington age 38 of the 15200 block of Lexington Avenue in Harvey, Illinois
Violent Suburban Criminal Robbing People in Chicago ... Harvey Gang Member Accused of Pulling Gun on Four People Across Two Districts in 15 Minutes
SubX.News® Crime Report Aug 28 2026
CHICAGO — Sylvester O. Whittington, 38, of south suburban Harvey, has been charged after allegedly robbing two people and threatening two others at gunpoint during three incidents across two Chicago police districts in 15 minutes.
Police say Whittington first approached a 27-year-old man at 8:34 p.m. May 14, 2026, in the 3500 block of North Central Avenue in the 16th District, produced a firearm and robbed him.
Eleven minutes later, a 48-year-old man was robbed at gunpoint in the 3000 block of North Pulaski Road in the 25th District.
Four minutes after that, two more people were allegedly threatened at gunpoint in the same block of North Pulaski Road.
In 15 minutes, Whittington allegedly pulled a gun on four people across two police districts before leaving the area.
Chicago police arrested him more than three months later, on August 26, in the 2700 block of South California Avenue.
Investigators identified Whittington as the person responsible for two armed robberies and an aggravated assault that occurred on May 14, 2026:
• 8:34pm 3500 block of N. Central Ave. (16th District); 27-year-old male victim robbed at gunpoint
• 8:45pm 3000 block of N. Pulaski Rd. (25th District); 48-year-old male victim robbed at gunpoint
• 8:49pm 3000 block of N. Pulaski Rd. (25th District); two victims threatened at gunpoint
He faces two felony counts of armed robbery with a firearm and two misdemeanor counts of aggravated assault with a deadly weapon.
Detention hearing was scheduled for August 27 at the Leighton Criminal Courthouse, 2600 South California Avenue.
History of Weapons, Gang and Violence-Related Arrests
Chicago Police Department records document at least 10 arrests involving Whittington between August 2014 and May 2026. These records reflect arrests and charges, not findings of guilt.
His most recent arrest before the current robbery case came on May 26, 2026, when officers took him into custody at 7631 S. East End Ave. That arrest lists four charges:
• Criminal sexual abuse/force
• Issuance of a warrant
• Two counts of domestic battery causing bodily harm
He was released on May 28, 2026.
Earlier arrests include allegations of armed habitual criminal conduct, possession or use of a firearm by a felon, possession of ammunition without a valid FOID card, and possession of prohibited high‑capacity magazines and metal‑piercing bullets.
Other entries include street‑gang contact while on parole, reckless conduct, controlled‑substance and cannabis possession, domestic battery causing bodily harm, multiple warrants, and traffic and licensing offenses such as driving with a suspended license, operating without insurance and having no valid vehicle registration.
Some arrests also involve soliciting unlawful business, obstructing traffic and other parole‑related violations.
Each original CPD entry is reproduced below with its statute, charge description, arrest location, release information and bond details.
His arrest history includes charges alleging armed habitual criminal conduct, possession or use of a firearm by a felon, possession of ammunition without a valid FOID card and possession of prohibited high-capacity magazines and metal-piercing bullets.
Other entries include street-gang contact while on parole, reckless conduct, controlled-substance possession, cannabis possession, domestic battery causing bodily harm and multiple warrants.
There is also a criminal sexual abuse/force charge in Whittington’s Chicago Police Department arrest history. His May 26, 2026, arrest also lists issuance of warrant and two separate entries of domestic battery/bodily harm. He was released May 28, 2026.
Earlier arrests included charges involving street-gang contact or parole violations, soliciting unlawful business, obstructing traffic, driving with a suspended license, operating without insurance and having no valid vehicle registration.
These records document arrests and charges, not findings of guilt.
Each original CPD entry is reproduced below with its statute, charge description, arrest location, release information and bond details.
Arrest History Chicago Police Deapartment
https://publicsearch1.chicagopolice.org/Arrests/History/16990794
Current Charges August 26 2026
Offender: Sylvester Whittington, 38
Address: 15200 block of S Lexington Ave Harvey Illinois
Arrested: August 26, 2026
Arrest location: 2700 block of S California Ave Chicago Illinois
Current Charges
Two (2) felony counts – Robbery – Armed with Firearm
Two (2) misdemeanor counts – Aggravated Assault/Use Deadly Weapon
Court: Detention Hearing – 2600 S California – August 27, 2026
https://x.com/TAhern_/status/2092999862740455804
May 26 2026
Name: SYLVESTER O WHITTINGTON Age: 37
CB Number: 30586557
Arrested: Tuesday, May 26, 2026 10:17 AM
Arrest Location: 7631 S EAST END AVE
Arresting Agency: CHICAGO POLICE DEPARTMENT
Released: Thursday, May 28, 2026 5:55 AM
Area: 2 - South District: 004 Beat: 0414
Charges
720 ILCS 5.0/11-1.50-A-1 CRIMINAL SEXUAL ABUSE/FORCE
725 ILCS 5.0/110-3 ISSUANCE OF WARRANT
720 ILCS 5.0/12-3.2-A-1 DOMESTIC BATTERY/BODILY HARM
720 ILCS 5.0/12-3.2-A-1 DOMESTIC BATTERY/BODILY HARM
https://publicsearch1.chicagopolice.org/Arrests/Details/18536379
March 16 2022
Name: SYLVESTER O WHITTINGTON Age: 33
CB Number: 30126682
Arrested: Wednesday, March 16, 2022 11:23 PM
Arrest Location: 3943 W 47TH ST
Arresting Agency: CHICAGO POLICE DEPARTMENT
Released: Thursday, March 17, 2022 7:00 AM
Area: 1 - Central District: 008 Beat: 0821
Charges
720 ILCS 5.0/24-1.7-A ARMED HABITUAL CRIMINAL
720 ILCS 570.0/402-C POSSESSION POSS AMT CON SUB EXCEPT
7-24-099(C)(6) USE CANNABIS IN PUBLIC PLACE
8-20-085(A) HIGH CAP MAG AND METAL PIERCING BULLETS
430 ILCS 65.0/2-A-2 POSS AMMUNITION - W/O VALID FOID
725 ILCS 5.0/110-3 ISSUANCE OF WARRANT
https://publicsearch1.chicagopolice.org/Arrests/Details/18073607
May 7 2018
Name: SYLVESTER O WHITTINGTON Age: 29
CB Number: 19640917
Arrested: Monday, May 7, 2018 11:47 PM
Arrest Location: 534 N AVERS AVE
Arresting Agency: CHICAGO POLICE DEPARTMENT
Released: Tuesday, May 8, 2018 8:20 AM
Area: 3 - North District: 011 Beat: 1122
Charges
720 ILCS 5.0/24-1.1-A UUW FELON, POSSESS/USE FIREARM
9-24-010(B) STOP AT STOP SIGN
625 ILCS 5.0/6-303-A DRIVING ON SUSPENDED LICENSE
https://publicsearch1.chicagopolice.org/Arrests/Details/17578216
October 30 2015
Name: SYLVESTER O WHITTINGTON Age: 27
CB Number: 19214031
Arrested: Friday, October 30, 2015 6:37 PM
Arrest Location: 116 N PULASKI RD
Arresting Agency: CHICAGO POLICE DEPARTMENT
Released: Friday, October 30, 2015 11:26 PM
Bond Type: DBOND Bond Amount: $2,000 Bond Date: 2015 Oct 30
Area: 3 - North District: 011 Beat: 1114
Charges
625 ILCS 5.0/6-303-A DRIVING ON SUSPENDED LICENSE
430 ILCS 85.0/2-14 OPERATE WITHOUT INSURANCE
625 ILCS 5.0/3-701-1 NO VALID REGISTRATION
https://publicsearch1.chicagopolice.org/Arrests/Details/17148539
March 30 2015
Name: SLYVESTER WHITTINGTON Age: 26
CB Number: 19088214
Arrested: Monday, March 30, 2015 6:56 PM
Arrest Location: 1537 S KOMENSKY AVE
Arresting Agency: CHICAGO POLICE DEPARTMENT
Released: Tuesday, March 31, 2015 7:12 AM
Area: 1 - Central District: 010 Beat: 1012
Charges
720 ILCS 5.0/25-5-A-4 STREETGANG CONTACT/PAROLE
720 ILCS 5.0/12-5-A RECKLESS CONDUCT
725 ILCS 5.0/110-3 ISSUANCE OF WARRANT
https://publicsearch1.chicagopolice.org/Arrests/Details/17021957
February 6 2015
Name: SYLVESTER WHITTINGTON
Age: 26
CB Number: 19057243
Arrested: Friday, February 6, 2015 11:00 AM
Arrest Location: 520 N SPRINGFIELD AVE
Arresting Agency: CHICAGO POLICE DEPARTMENT
Released: Saturday, February 7, 2015 1:54 AM
Bond Type: DBOND Bond Amount: $1,500 Bond Date: 2015 Feb 07
Area: 3 - North District: 011 Beat: 1122
Charges
720 ILCS 5.0/25-5-A-4 STREETGANG CONTACT/PAROLE
https://publicsearch1.chicagopolice.org/Arrests/Details/16990794
January 27 2015
Name: SLYVESTER WHITTINGTON Age: 26
CB Number: 19052052
Arrested: Tuesday, January 27, 2015 2:10 PM
Arrest Location: 501 N HARDING AVE
Arresting Agency: CHICAGO POLICE DEPARTMENT
Released: Wednesday, January 28, 2015 5:35 AM
Area: 3 - North District: 011 Beat: 1122
Charges
720 ILCS 550.0/4-C CANNABIS - POSSESS 10-30 GRMS
https://publicsearch1.chicagopolice.org/Arrests/Details/16985547
January 22 2015
Name: SLYVESTER WHITTINGTON Age: 26
CB Number: 19049015
Arrested: Thursday, January 22, 2015 4:01 PM
Arrest Location: 449 N HARDING AVE
Arresting Agency: CHICAGO POLICE DEPARTMENT
Released: Thursday, January 22, 2015 10:03 PM
Bond Type: IBOND Bond Amount: $120 Bond Date: 2015 Jan 22
Area: 3 - North District: 011 Beat: 1122
Charges
10-8-515 SOLICITING UNLAWFUL BUSINESS
https://publicsearch1.chicagopolice.org/Arrests/Details/16982490
December 19 2014
Name: SYLVESTER OMAR WHITTINGTON Age: 26
CB Number: 19031377
Arrested: Friday, December 19, 2014 11:40 AM
Arrest Location: 3927 W FERDINAND ST
Arresting Agency: CHICAGO POLICE DEPARTMENT
Released: Friday, December 19, 2014 5:20 PM
Bond Type: IBOND Bond Amount: $120 Bond Date: 2014 Dec 19
Area: 3 - North District: 011 Beat: 1122
Charges
10-8-515 SOLICITING UNLAWFUL BUSINESS
https://publicsearch1.chicagopolice.org/Arrests/Details/16964717
August 27 2014
Name: SYLVESTER OMAR WHITTINGTON Age: 26
CB Number: 18963503
Arrested: Wednesday, August 27, 2014 10:10 AM
Arrest Location: 465 N HARDING AVE
Arresting Agency: CHICAGO POLICE DEPARTMENT
Released: Wednesday, August 27, 2014 5:50 PM
Bond Type: IBOND Bond Amount: $120 Bond Date: 2014 Aug 27
Area: 3 - North District: 011 Beat: 1122
Charges
9-80-180 OBSTRUCTION OF TRAFFIC BY NON-MOTORIST
https://publicsearch1.chicagopolice.org/Arrests/Details/16896396
Sources: Chicago Police Department | Chicago Crime Chaser
