Milwaukee County Executive and Democratic gubernatorial nominee David Crowley is facing backlash from left-wing criminal justice organizations over his decision to suspend inmate tablet messaging at the county’s Community Reintegration Center. This reversal came after weeks of mounting scrutiny over inmates using the devices to threaten and intimidate crime victims and witnesses.
According to an October 13 Wisconsin Examiner report, several criminal justice advocacy organizations expressed disappointment with Crowley’s decision, arguing that he was restricting an important means of communication for incarcerated individuals in response to Republican political attacks.
Among those criticizing Crowley was Black Leaders Organizing Communities (BLOC), a Milwaukee-based progressive organization that supported his gubernatorial campaign earlier this year.
“We have to be careful in giving in to the narrative of Republicans and their methods to make incarcerated people as uncomfortable as possible,” the organization told the Wisconsin Examiner.
Marianne Oleson, co-executive director of Ex-Incarcerated People Organizing (EXPO), similarly argued that inmates and their families should not lose access to communication services because of others’ misconduct. Roy Rogers, a board member of the Wisconsin Justice Initiative and leader of Milwaukee’s Onesimus Group, also defended electronic messaging as an important tool for maintaining family relationships and preparing inmates for reentry into society.
The criticism places Crowley in an uncomfortable political position, caught between criminal justice organizations that have championed the inmate-friendly policies he has supported throughout his political career and growing scrutiny over his administration’s failure to prevent inmates from using taxpayer-funded communications services to terrorize victims.
From “Best Practice” to Political Liability
As The Heartland Post previously reported, Crowley ordered the Community Reintegration Center (CRC) to disable tablet messaging on October 9 while officials worked to implement additional safeguards. He also urged Milwaukee County Sheriff Denita Ball to take similar action at the county jail.
The announcement marked a significant reversal for Crowley, who personally signed the county’s communications contract with ICSolutions in 2022 and later approved a three-year extension through March 2028.
His administration had previously defended the program as a criminal justice “best practice,” even as repeated incidents raised serious questions about inmate communications and victim safety.
Among the most troubling cases was Thomas Zollicoffer, a defendant charged with three counts of first-degree intentional homicide in connection with an August triple murder in Milwaukee.
According to prosecutors, Zollicoffer used his jail-issued tablet to communicate threats directed at a witness, prompting Milwaukee County Circuit Court Judge David Borowski to question why violent defendants were being provided electronic communication devices.
Republican gubernatorial nominee Tom Tiffany subsequently featured Borowski’s remarks in a campaign advertisement criticizing Crowley’s handling of the program.
Other cases documented by The Heartland Post included an inmate accused of contacting a domestic violence victim 2,439 times, another who allegedly attempted to contact a victim more than 1,500 times despite a no-contact order, and a third accused of sending 164 messages to a woman he was charged with strangling.
The controversy has also extended to the program’s financial costs. A previous Heartland Post investigation found that Milwaukee County taxpayers are spending more than $1 million annually to provide free phone minutes and video visitation services to inmates under budgets signed by Crowley.
Crowley’s Campaign Tried to Silence Tiffany’s Ad
Rather than immediately addressing the concerns raised in Tiffany’s advertisement, Crowley’s campaign initially attempted to have it removed from the airwaves.
As exclusively reported by The Heartland Post, on September 23, the campaign sent Tiffany a cease-and-desist letter accusing him of making false and defamatory statements.
The letter contained several questionable arguments, including repeatedly misidentifying Judge David Borowski as “Daniel Borokowski” and objecting to the advertisement’s use of courtroom footage originally recorded by CBS 58 with judicial permission.
Perhaps most remarkably, Crowley’s campaign argued that Tiffany’s description of the devices as “iPads” was defamatory because they were technically generic tablets rather than Apple-branded devices. That distinction did little to address the underlying allegations that inmates were using the devices to intimidate victims and witnesses.
Less than three weeks after threatening legal action over Tiffany’s advertisement, Crowley reversed course and suspended messaging at the CRC.
Tiffany has accused Crowley of only standing up for crime victims when it became politically convenient.
“Since May, [Crowley] has known about reports of inmates using the tablets he approved to threaten victims,” Tiffany said in a statement. “Yet he continued to defend the program as ‘best practice,’ even as an accused triple murderer and an alleged domestic abuser used them to intimidate victims and witnesses from jail. David Crowley will only protect victims when it benefits him.”
For Crowley, who has spent much of his political career championing progressive criminal justice reforms and policies that expand services for inmates, the backlash from the left represents an unusual political predicament.
After weeks of defending the program, challenging Tiffany’s advertisement, and ultimately suspending messaging services, Crowley now faces questions about why it took repeated allegations of victim intimidation and mounting political pressure to prompt a policy change.
Crowley’s reversal may have been intended to put the controversy behind him, but instead, it has left him facing criticism from both sides—and renewed questions about whether protecting crime victims was ever his administration’s top priority.
