Voters To Choose Between Bobby Richardson, Jose Villagrana For Kendall County Sheriff

KENDALL COUNTY, IL — Democrat Jose Villagrana and Republican Bobby Richardson will go head-to-head for the Kendall County sheriff role in the Nov. 3 election.

It'll be the first time since 2014 that Kendall County sees a new sheriff.

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Incumbent Sheriff Dwight Baird announced in 2025 that he would not seek another term. He endorsed Richardson, his longtime undersheriff, as his successor, WSPY News reported.

Both Villagrana and Richardson ran unopposed in the March primaries.

Richardson, whose law enforcement career began in 2007 as a patrol deputy, has served as undersheriff to Baird since November 2019. He worked in patrol, investigations, community policing, corrections, undercover operations, supervision and command throughout his career.

"Preparation is a big part of what I do every day as Undersheriff," Richardson, a United States Marine Corps veteran, wrote on his Facebook campaign page. "It happens long before a call comes in… the people we hire, the training and equipment we provide and the relationships we build with neighboring departments. I've spent nearly twenty years learning this office and the past seven helping lead it. I would be grateful for the opportunity to continue that work as Sheriff."

Richardson said he also wants more community outreach, more focus on mental health at the sheriff's office, and to share police services and staff in order to save taxpayer money, according to a report from WSPY News.

A retired Kendall County deputy and part-time attorney, Villagrana is running on a platform rooted in affordability and accountability.

His plans, if elected, include ending understaffing and prioritizing on-the-ground deputies by reducing excess upper-level positions. Cutting down on the "bloated" upper command would free up an estimated $400,000 to $500,000 to hire, train and retain deputies, according to his campaign website.

Villagrana, whose career in law enforcement lasted 25 years, said he is committed to serving Kendall County "in a just and impartial manner—keeping the community safe through professionalism, transparency, and respect for every resident, without shortcuts and without favoritism."

The polls will be open from 6 a.m. to 7 p.m. on Election Day.