GOP candidate Darren Bailey uses trespassing arrest at JB Pritzker's home for familiar attack on crime

CHICAGO - In an era of rising concern over the safety of elected officials and other political figures, Republican governor nominee Darren Bailey is using the July 4 arrest of a man who allegedly jumped a fence into the backyard of Gov. JB Pritzker's Gold Coast home as a way to score political points and solicit campaign contributions.

Bailey, a conservative southern Illinois farmer and former state lawmaker who's challenging the Democratic governor for the second straight election, highlighted the incident in a fundraising email sent Wednesday under the subject line "Pritzker gets a taste."

The message, sent hours before Bailey's campaign reported lackluster fundraising numbers for the three months that ended June 30, sounded familiar tones from the GOP candidate's tough-on-crime campaigns, linking an alleged crime to a criminal justice overhaul Pritzker signed that included the 2023 elimination of cash bail.

After giving a summary of the alleged crime that conflicts with police records, the fundraising email continues: "Because of Pritzker's SAFE-T Act, this repeat offender was allowed to offend once again!

"J.B. gets a taste of his own medicine.

"If a criminal out on electronic monitoring can break into the Governor's own home, we have a problem."

It's unclear, however, whether Dwayne Cortez Milton, 46, the man charged with trespassing at Pritzker's Astor Street home, would have been kept in jail while awaiting trial on a previous charge before passage of the Safety, Accountability, Fairness and Equity-Today law.

Police in the Near North (18th) District responded about 10 p.m. July 4 to a call to assist an Illinois State Police officer at the governor's home. According to a Chicago police arrest report contained in court records, Milton allegedly jumped the fence into the backyard.

Milton "gained access to the inside of the property," according to the report, though it wasn't clear whether he'd made it inside a building. No reason was given in the report for Milton's actions. The Illinois State Police has not yet released its report on the incident pending a request under the Freedom of Information Act.

At the time he was arrested, authorities had issued a separate warrant for Milton stemming from his failure to appear in court and alleged curfew violations in a retail theft case, court records show.

Milton had originally been caught shoplifting about $55 worth of merchandise from an Uptown Walgreens in late April and was released on electronic monitoring, court records show. After he missed a court date and pretrial officers alleged he'd been caught tampering with his ankle monitor, authorities rearrested him and kept him in custody for about six weeks, records show.

Cook County Judge Aleksandra Gillespie ordered him rereleased June 17, records show. A second pretrial monitoring report, filed June 25, said Milton had racked up a half dozen "alerts" while on electronic monitoring for violating his 8 p.m. curfew.

When he didn't show up to court June 25, Gillespie issued a warrant for his arrest. The alleged trespassing at Pritzker's mansion took place slightly more than a week later.

After the July 4 arrest, Cook County Judge Shauna Boliker ordered Milton not to go near the property or have any contact with the state trooper who reported him to authorities. But records show Milton remained in custody and pleaded guilty July 8 to the original retail theft charge. He was sentenced to a year in the Illinois Department of Corrections and currently is being held at Stateville Correctional Center near Joliet.

Milton is next set to appear in court on the trespassing charge July 27, court records show.

State prison records show Milton has previously done years behind bars for burglary, retail theft, drug possession, armed robbery and aggravated battery, among other convictions, stretching back to the late 1990s.

Pritzker campaign spokesperson Alex Gough declined to answer questions about Bailey's fundraising email or the trespassing incident itself, including whether the governor or any family members were home at the time.

A Bailey spokesperson did not respond to questions about whether it had evidence suggesting Milton would have remained detained under the cash bail system Pritzker abolished or whether it was appropriate to use an alleged crime at an opponent's home as a fundraising tool and campaign attack line.

There has been widespread concern across the political spectrum in recent years over rising political violence and broader threats to the safety of elected officials and other political figures.

In October, a man pleaded guilty to attempted murder for setting fire to and breaking into the official residence of Pennsylvania Gov. Josh Shapiro in April 2025 while the Democrat and his family slept inside.

This April, a man armed with guns and knives was charged with attempted assassination after infiltrating the Washington hotel where President Donald Trump was attending the White House Correspondents' Association dinner.

Milton's arrest isn't the first time Pritzker's Chicago home has been used as a political backdrop.

In September, a right-wing commentator for the Real America's Voice network posted a video to social media from outside the home in which he called the governor a "scumbag" and a "worthless politician," blaming political violence on "leftist Democrat policies, who took God out of society, replaced God with government."

The commentator, Ben Bergquam, was among many on the right who criticized Pritzker publicly for linking the killing of conservative activist Charlie Kirk to the broader trend of rising political violence and Trump's political rhetoric.

In his second run for governor, after losing to Pritzker by 13 percentage points in 2022, Bailey is again focusing much of his attention on crime and criticism of the SAFE-T Act, a law Pritzker signed in 2021. Part of that overhaul was the Pretrial Fairness Act, which went into effect in September 2023 after being tied up in court.

Politicians on the right, from Bailey to Trump, have frequently used Illinois' move to eliminate money bond as a cudgel against Democrats, blaming Chicago's violent crime on the change.

Supporters of the legislation, though, including some local prosecutors, point out that the law means judges consider risk to the community and propensity to flee as factors in whether to release a defendant pretrial - not their wealth or ability to pay bail. In other words, they've argued, no one can pay their way out of jail if they pose a risk to the community.

Before the passage of the Pretrial Fairness Act, judges did have more discretion to detain people. A key part of law, which has been the subject of much of the debate over public safety over the past five years, deems certain offenses "non-detainable," meaning judges do not have the option to order defendants jailed if facing those charges. They tend to be lower-level offenses and crimes of poverty, though whether judges should regain more discretion in those cases has been debated in some corners.

But before the implementation of the new law, defendants accused of such offenses were often granted release through a proportional bail amount, or even a personal recognizance bond, which meant no upfront money was required for release.

In instances where a defendant was rearrested while awaiting trial in another case, it was not uncommon for defendants to cycle through stints in jail, then be released on bail.

In fact, although Cook County Jail's population decreased after the Pretrial Fairness Act took effect, it has since increased, with about 500 more inmates there now than in the month before the law took effect.

The landmark legislation, which made Illinois the first state to outlaw money bail, also sought to remedy inequities in the pretrial system through a number of other changes. It made procedural changes to the law intended to lengthen the time judges spent reviewing the circumstances of a case, an attempt to avoid previous cattle-call-like court hearings in which decisions on whether to grant release were made in minutes.

Its effect is still being studied, but supporters have pointed out that its passage has not been accompanied by increases in violent crime.

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This story was originally published July 18, 2026 at 8:52 PM.