JB Pritzker has spent five years telling Illinois that abolishing cash bail makes communities safer.
Now a 10-time convicted felon who spent six straight nights evading his ankle monitor – while Cook County did nothing – just climbed the fence into the governor's own Gold Coast mansion.
What happened next is something Pritzker has no answer for.
The Ankle Monitor That Nobody Watched
Dwayne Cortez Milton, 46, was placed on electronic monitoring June 17 after picking up a felony retail theft charge – while already on pretrial release for a separate shoplifting case.
For six consecutive nights, Milton went dark on the Cook County monitoring system before the matter was ever reported to a judge.
Cook County Chief Judge Charles Beach had publicly pledged that "major violations" would reach a judge within 24 hours.
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That pledge was not honored.
By the time authorities located Milton again – 11 days after his disappearance began – he was scaling the rear fence of Pritzker's Gold Coast residence.
Illinois State Police troopers on the governor's security detail caught him on camera and detained him at 10 p.m. on Independence Day.
Sixty Cases, Ten Convictions, One Ankle Monitor
Milton's felony convictions include burglary, retail theft, and robbery – part of a Cook County court history spanning more than 60 cases.
That is the man Pritzker's system kept on the street with an ankle bracelet instead of behind bars.
Cook County State's Attorney Eileen O'Neill Burke had already been sounding this alarm.
After a separate repeat offender on electronic monitoring allegedly set a woman on fire aboard a Chicago Blue Line train in November 2025, Burke made the system's failure explicit.
"If you're putting a violent offender on electronic monitoring, we believe that you are endangering the public by doing so," Burke said – pointing out that monitoring personnel are not law enforcement and cannot detain anyone who disappears.
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That Blue Line suspect had violated his own monitoring conditions at least five times in the days before the attack.
Nothing happened to him either.
Pritzker Wants to Run for President on This Record
Illinois Republicans were merciless after the July 4 incident.
"A 10-time convicted felon slips his electronic monitor. The court isn't told for days. He's found in JB Pritzker's own backyard. How many more warnings does Illinois need before we admit the SAFE-T Act is failing," wrote GOP gubernatorial candidate Darren Bailey.
Illinois Review contributor Mark Weyermuller was more direct: "The Governor is a victim of his own soft on crime policy."
Pritzker, widely floated as a 2028 Democrat presidential candidate, signed the SAFE-T Act in 2021 – making Illinois the first state in America to abolish cash bail.
He has backed the law ever since – even as Chicago thefts climbed 7% year over year, even as Trump demanded he accept federal help on the city's violence, even as his own state's attorney publicly warned that electronic monitoring was putting people at risk.
Chicago has led the nation in total homicides for 13 straight years.
Trump called Pritzker out directly in June after 39 people were injured and four killed over a single weekend, posting on Truth Social: "Governor JB Pritzker should pick up the phone and call me."
Pritzker rejected the offer.
The SAFE-T Act Is Working Exactly as Designed
That is the part Pritzker will never say out loud – but the record makes it undeniable.
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The SAFE-T Act was built to keep people like Dwayne Milton out of pretrial detention.
It eliminated cash bail and made it substantially harder for prosecutors to argue that repeat offenders should be held before trial.
Beyond the Act itself, Pritzker has compounded it – opposing mandatory minimum expansions and broadening parole eligibility as a matter of policy.
The result is a monitoring system where a man with a 60-case criminal history walks free, vanishes for nearly two weeks, and nobody is legally empowered to go find him.
That is not a system that broke down.
The only difference on July 4 was that Milton picked the wrong backyard.
Every other Illinois neighborhood has no security cameras on round-the-clock watch, no state trooper detail, no trained eyes on the fence line.
The governor does.
Sources:
- Tim Hecke, "10x felon escapes from electronic monitoring – until he's found in the Governor's back yard," CWB Chicago, July 12, 2026.
- Ashley J. DiMella, "Pritzker skewered as 'victim of his own' policy after repeat offender arrested in governor's backyard," Fox News, July 14, 2026.
- "Cook County electronic monitoring system under scrutiny after woman set on fire on CTA train," CBS Chicago, November 26, 2025.
- "State reps: Pritzker turns 'blind eye' to Chicago's public safety crisis," The Center Square, November 24, 2025.
- "Trump slams Pritzker on Chicago crime as governor's reported weight loss fuels 2028 speculation," Fox News, August 31, 2025.