(Kenosha County Sheriff’s Office)
PLEASANT PRAIRIE, Wis. — A Markham, Illinois man accused in a smash-and-grab burglary at the Pleasant Prairie JCPenney walked out of jail Wednesday after Liberal Activist Supplemental Court Commissioner David Hughes cut his cash bail from $15,000 to $2,000.
(File Photo by Kevin Mathewson, Kenosha County Eye)
Nathaniel A. Montgomery, 51, was arrested and brought into court on Wednesday, Nov. 5, 2025, where Hughes reduced the previously ordered $15,000 cash warrant to $2,000. Montgomery posted the lower amount and was released pending further proceedings. His co-defendant, Jaqueil T. Smith, 22, of Madison, remains wanted on the original warrant and has not yet appeared.
The case stems from a Feb. 29, 2024 pre-dawn break-in at the Pleasant Prairie JCPenney in which four masked suspects used a mallet to shatter the front doors, sprinted to the jewelry department, smashed display cases, and fled within minutes in a white SUV with obscured plates. Investigators documented blood drops, clothing fibers and latent prints, and later received crime-lab and cross-agency leads tying the Pleasant Prairie burglary to a broader Chicago-area crew hitting stores across multiple Wisconsin jurisdictions. In one linked case, investigators recovered photos of JCPenney jewelry hours after the Pleasant Prairie break-in, and a store manager identified UPC codes as matching merchandise taken from the damaged clearance case.
Kenosha County opened two linked files on October 14, 2025: 2025CF001472 for Montgomery and 2025CF001470 for Smith. On that date, Court Commissioner Michael issued a $15,000 cash arrest warrant. According to Wednesday’s in-court proceedings, Hughes reduced Montgomery’s cash requirement to $2,000, enabling his release the same day. Smith’s warrant remains active.
Montgomery is charged with Burglary of a Building or Dwelling (Class F felony). If convicted, he faces a maximum of 12 years, 6 months in prison and a $25,000 fine.
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11 Responses
I’m so sick of these liberal DA’s and judges. This guy needs the maximum bail! He is never going to learn if these DA’s and judges are soft on crime!
Check out the 8th Amendment, bro. Constitutional protection against excessive bail.
Giving insufficient bail poses no danger to the 8th amendment, I’m sure most of us would be quite pleased to just see sufficient bail based on the charges and past history.
So Bond is supposed to be given to assure the defendants will appear. The co-defendant in this case has a warrant and hasn’t been arrested yet. I would think this would be a good case for the higher bond given the fact the other guy is still at large. The bond in this town is a joke and all the reasoning behind it, never makes sense. The defendant is out of state, is part of a crew doing this to stores, but at least he wasn’t given a signature bond. WTF
Black Friday sale ?
What possible reason would he lower his bond?loser.
Bond that was originally set on a warrant is always (by law) reviewed at the initial appearance. It could stay the same, be raised or lowered but a new bond is always set.
Walking through this, Commissioner Michel usually doesn’t have any information about a defendant’s background when setting bond on a warrant. He just gets a copy of the criminal complaint and proposed warrant (in fact, not even a hard copy but it shows up on his computer). Rarely will a DA be present to make a bond argument.
By contrast, Commissioner Hughes had a prosecutor in court to make a bail argument (What did the prosecutor ask for bail?) and hopefully the prosecutor informed him of the defendant’s prior record, if any. Given the base line circumstances here, including that the defendant is from out-of-state $2,000 cash was very low. $5,000 would be on the low end, normally, and $10,000-$15,000 in the mid-to-upper range and that could go higher if there were missed court appearances, a significant record or something special about the case (like stealing guns or residential burglary).
Hughes looks like a light bulb that’s not to bright.
We can all piss and moan about bail that we feel is set too low but at least our Wisconsin judges still get to set cash bail. There are states where that’s not the case.