This is as brutal as it is funny. For weeks, Milwaukee County Executive and Democrat gubernatorial candidate David Crowley ignored the California-esque scandal caused by his inmate tablet program. At least four inmates that we know of have used the tablets — a program authorized by Crowley — to intimidate witnesses, harass their victims, and threaten law enforcement.
This includes Thomas Zollicoffer, who is charged with the murder of his ex-girlfriend and two others; Zollicoffer was using his tablet to intimidate witnesses. Milwaukee County Judge David Borowski slammed the program and revoked Zollicoffer's privileges. Damien Luis Cosme-Torres and Amier Jones both abused the tablet program. Cosme-Torres sent threatening messages to his victim and Jones did the same to his victim. Jones also put a Milwaukee police officer on a hit list. Last week, Kahney Ali-Powells was discovered using his tablet to send more than 160 messages to his victim.
On September 29, Crowley refused to pause or rescind the program and said in several interviews over the last couple of weeks that the tablet program was actually a "best practice."
It's clear the scandal was damaging his campaign, because Crowley finally suspended the program on October 10. The drama didn't stop there, however. Crowley's campaign tried to get his Republican opponent, Tom Tiffany, to stop talking about the scandal — going so far as to send a cease-and-desist letter to the Tiffany campaign.
But things got even worse for the Crowley campaign. That cease-and-desist letter — a joke in and of itself — was full of basic and embarrassing errors, too. Including misidentifying Judge David Borowski as "Daniel Borokowski."
David Crowley's campaign was so scared of his 'iPads for Inmates's scandal that it sent a panicked cease-and-desist letter to the Tiffany campaign filled with basic errors such as identifying Judge David Borowski as "Daniel Borokowski."
— The Heartland Post (@HeartlandPostWI) October 13, 2026
Get the full story from @DanODonnellShow in… pic.twitter.com/0ZrIDWIKcZ
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The letter, originally published by The Heartland Post, reads in part (emphasis added):
This firm represents Crowley for Wisconsin. I have investigated the advertisement put out by Tiffany for Wisconsin (the “Tiffany Campaign”) entitled, “Preposterous.”¹ This ad not only violates Wisconsin Supreme Court Rules and potentially Wisconsin campaign finance law, but also contains numerous statements that are actionable as defamation and violations of Wisconsin election law.
Accordingly, by this letter, the Tiffany Campaign is hereby demanded to immediately pull down this advertisement and cease and forever desist airing this advertisement. Should Tiffany Campaign ignore this warning, it does so at its own legal peril.
First, the ad is almost certainly in violation of Wisconsin’s Cameras in the Courts rules, in at least two ways. See Wis. Stat. ch. SCR 61. The ad contains video of a court proceeding and depicts Milwaukee County Circuit Court Judge Daniel Borokowski speaking during the proceeding. The Cameras in the Courts rules prohibit recording court proceedings without prior permission of the court being filmed, and they do not distinguish between proceedings that are in person or on streaming platforms, such as those offered by the courts.² E.g., id. §§ SCR 61.02(2), 61.03. Revealingly, the video of Judge Borowski is not sourced at all, and there is no indication on the applicable court docket that permission was received to record the proceedings. This leads to the inevitable inference that the Tiffany Campaign or a proxy impermissibly recorded the proceedings to use in a baseless political attack ad.
Moreover, Wis. Stat. § SCR 61.12 explicitly reserves the right to “photograph, televise, and record court proceedings” to only persons or organizations that are part of the news media, and prohibits any “film, videotape, photography and audio reproductions” from being used for “unrelated advertising purposes.” The “Preposterous” ad is clearly using “film,” “videotape,” and “audio reproductions” of a court proceeding for a political advertisement, in violation of these rules. Wisconsin campaign finance law provides that no person may “intentionally receive or accept anything of value … constituting a disbursement made contrary to law.” Wis. Stat. § 11.1208(1). Disbursements include “an expenditure by a committee from the committee’s depository account.” Wis. Stat. § 11.0101(10)(a)(1.).
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Second, the ad contains statements that are misleading and false. The ad flashes a graphic which states that “David Crowley Approved iPads to Inmates.” This statement is false. As the Milwaukee County Sheriff Jail Director has publicly stated, inmates are only provided access to “generic tablets,”³ not “iPads.” These tablets do not allow for video or phone calls; are not connected to the internet and can only access a closed, provider-managed network; and are commonly used in correctional settings across Wisconsin and the country.⁴ Then, after falsely claiming that inmates are provided “iPads,” the next immediate statement asserts that “one domestic abuser is accused of contacting a victim 1,500 times.” Given the context of the preceding graphic, the ad implies that the inmate contacted the victim 1,500 times using an iPad or tablet. Once again, this is false. Court records show that the inmate attempted 1,535 phone calls using the jailhouse phone and video-calling system, not through the tablet program.⁵ Finally, the ad cites an unverified claim that an inmate purportedly accessed child pornography through the tablet program in jail. In fact, the Milwaukee County Sheriff has said that would be “impossible.”⁶
On this basis, the Tiffany Campaign is likely liable for defamation. The elements of a claim for defamation include: 1) a false statement; 2) communicated by speech, conduct or in writing to one other than the one defamed; and 3) the communication is unprivileged and tends to harm one’s reputation, lowering him in the estimation of the community or deterring third persons from associating or dealing with him. Laughland v. Beckett, 2015 WI App 70, ¶ 22, 365 Wis. 2d 148. These elements apply to implication and insinuation, not just direct statements, including juxtaposition of audio and video statements of the ad together. Mach v. Allison, 2003 WI App 11, ¶ 31, 259 Wis. 2d 686.
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Similarly, the advertisement is likely a violation of Wis. Stat. § 12.05, which provides that “[n]o person may knowingly make or publish, or cause to be made or published, a false representation pertaining to a candidate or referendum which is intended or tends to affect voting at an election.” Wis. Stat. § 12.05 (“False Representations Affecting Elections”). The Wisconsin Elections Commission may investigate any such violation and pursue civil remedies against the Tiffany Campaign, including seeking fines and injunctive relief. Wis. Stat. § 5.05(1)(c);(d). What’s more, upon a finding of probable cause that a violation occurred, the Commission may refer any violation of Wis. Stat. § 12.05 for criminal prosecution to the District Attorney in the county where the matter arises. Wis. Stat. § 5.05(2m)(11).
Ultimately, this advertisement unlawfully politicizes and weaponizes the Wisconsin criminal justice system and likely contains several defamatory and false statements. Accordingly, by this letter, the Tiffany Campaign is hereby demanded to pull down this advertisement and cease and forever desist airing this advertisement.
Dan O'Donnell breaks down the — forgive the pun — preposterous arguments in this letter.
"The letter further argues the ad violates Wisconsin Supreme Court Rules on cameras in the courts, which prohibit recording proceedings without prior permission and restrict such recordings to news media," O'Donnell wrote. "However, the proceeding was recorded by the news media and then used in a political advertisement. Courts have long allowed this practice."
As to the use of the term iPad, O'Donnell notes, the "term 'iPad' is often used to refer to any sort of tablet device and is commonly understood as a genericized trademark. Like 'Kleenex' is commonly used to refer to tissue paper, so too is 'iPad' commonly used synonymously with 'tablet.'"
We know the iPads scandal is a massive liability for the Crowley campaign because he:
— RightWI (@RightWI1776) October 13, 2026
1. Abruptly changed his position on it mere weeks before election day
2. Sent a sloppy Cease and Desist letter asking the Tom Tiffanu campaign to stop talking about it https://t.co/tz6QHk9QR1
This reeks of desperation from a failing campaign.
— Jason Szemborski (@JasonSzemborski) October 14, 2026Continuing to put ineptness on full display... failure to renew health insurance, cease-and-desist full of errors, no actual plan or platform to campaign on.
And this guy wants to be Governor of Wisconsin?!
No thanks! https://t.co/ozPnysZc0O
Everything in that ad was factual and accurate. As County Executive, David Crowley signed off on the program in 2022 and reauthorized it last year. He gave interviews where he called it a "best practice." The only reason — the only reason — he changed is tune is because this was hurting him politically.
Outside of Milwaukee and Dane, there are 70 counties that don't look kindly on Milwaukee. They see it as a crime-ridden cesspool that sucks state tax dollars. Crowley has done nothing to disprove that, and now his campaign has made an even bigger fool of him.
Editor’s Note: The 2026 Midterms will determine the fate of President Trump’s America First agenda. Republicans must maintain control of both chambers of Congress.
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