Defending The Windy City with David Drwencke
”Defending the Windy City” is your gateway to a captivating exploration of the legal landscape, hosted by seasoned criminal defense attorney David Drwencke. Join us as we delve into the intricacies of the justice system, dissecting critical topics that impact individuals and communities in Chicago and beyond.
Each episode of ”Defending the Windy City” brings you deep insights, expert analysis, and thought-provoking discussions on various legal matters. From navigating complex criminal defense cases to understanding legislative reforms, our show provides a comprehensive view of our society’s legal challenges and opportunities.
Whether you’re a legal professional, a concerned citizen, or simply curious about the workings of the legal system, ”Defending the Windy City” offers a unique blend of education and entertainment that will leave you informed and inspired.
Don’t miss an episode—subscribe now and join us on this enlightening journey of legal discovery with ”Defending the Windy City”!
Episodes

2 hours ago
2 hours ago
Episode Summary:
In this episode, David Drwencke delves into Illinois weapons charges, shedding light on common misconceptions and types of offenses. From unlawful use of a weapon to concealed carry complexities, David unravels the legal nuances and offers strategies for fighting back against overreaching prosecutors.
Key Timestamps:
00:00 – Introduction
01:30 – Types of weapon charges in Illinois
03:45 – Understanding unlawful use of a weapon (UUW)
05:20 – Common scenarios leading to weapon charges
07:10 – Importance of FOID card and concealed carry license (CCL)
09:45 – Arrests for weapons offenses despite compliance with the law
12:30 – Evidence used by prosecutors in weapons cases
14:15 – Recent shifts in public policy affecting prosecution of gun cases
16:40 – Defense strategies in weapons cases
18:55 – Success story: Mitigation leading to reduced sentence
21:10 – Closing remarks on avoiding escalation from minor offenses to serious charges
About the Show:
Defending the Windy City is a legal podcast hosted by a seasoned criminal defense attorney, focusing on navigating complex legal issues with expertise and insights. Join us to explore various legal topics and learn how to protect your rights in the legal system.

Monday Dec 01, 2025
Monday Dec 01, 2025
Episode Summary
In this episode of Defending the Windy City, criminal defense attorney David Drwencke, founding partner of DRD Law, explores how technology is transforming criminal defense. From digital discovery tools to secure client communication portals and AI-powered evidence analysis, Drwencke explains how these innovations give his firm a competitive advantage in and out of the courtroom. He also shares how technology helps clients feel informed, supported, and connected throughout their legal journey while ensuring the human, personal touch of defense remains at the forefront.
Key Timestamps
00:55 – The role of technology in criminal defense cases03:00 – How digital discovery tools optimize evidence review05:00 – The benefits of DRD Law’s client communication portal07:45 – Using technology to uncover prosecution errors and inconsistencies10:00 – How clients respond to digital transparency and fast updates12:45 – Leveraging technology inside the courtroom for impeachment and timelines15:45 – Balancing cutting-edge tools with personal client connections18:30 – Key questions clients should ask when hiring a defense attorney about technology
About the Show:
Defending the Windy City with attorney David Drwencke takes listeners inside the courtroom battles and legal strategies shaping criminal defense in Chicago and beyond. With years of experience as a judicial law clerk and criminal defense attorney, David shares real-world insight into protecting defendants’ rights, exposing flaws in prosecutions, and fighting for fairness in the justice system.

Monday Nov 10, 2025
Monday Nov 10, 2025
Episode Summary:
In this episode of Defending the Windy City, criminal defense attorney David Drwencke, founding partner of DRD Law, concludes his three-part series inspired by Simon Sinek’s Golden Circle. Having explored his “why” and “how” in earlier episodes, David now turns to the “what”—the real work DRD Law performs every day in courtrooms across Chicago and beyond.
David outlines the types of cases his firm handles, from misdemeanors to serious felonies, and shares how DRD Law builds trust, manages expectations, and guides clients through the intimidating criminal justice process. He explains why every case, no matter how small, is treated with equal seriousness, and how his team measures success not only by verdicts but also by the long-term impact on clients’ lives.
This episode provides a rare behind-the-scenes look at the scope of criminal defense work, the strategies behind effective representation, and the mission that drives DRD Law to deliver life-changing results for its clients.
Key Moments in This Episode
1:00 – The range of criminal cases DRD Law takes on3:15 – Why discovery is central to building a defense5:00 – Helping first-time offenders manage fear and expectations7:30 – Lowering anxiety for clients facing serious charges10:10 – Treating every case with equal seriousness and respect12:45 – Defining real success beyond verdicts15:20 – How plea agreements can sometimes be victories18:00 – Why clients should never fear reaching out for help19:30 – Staying connected to DRD Law’s mission and purpose
About the Show:
Defending the Windy City with attorney David Drwencke takes listeners inside the courtroom battles and legal strategies shaping criminal defense in Chicago and beyond. With years of experience as a judicial law clerk and criminal defense attorney, David shares real-world insight into protecting defendants’ rights, exposing flaws in prosecutions, and fighting for fairness in the justice system.

Tuesday Oct 21, 2025
Tuesday Oct 21, 2025
Episode Summary:
In this episode of Defending the Windy City, criminal defense attorney David Drwencke, founding partner of DRD Law, continues his three-part series inspired by Simon Sinek’s Golden Circle. After exploring his “why” in Episode 18, David now reveals the “how”—the practical strategies, tools, and values that drive his courtroom success.
From leveraging cutting-edge technology and AI to maintaining client trust through communication and empathy, David explains how DRD Law blends innovation with personal dedication to deliver results. He shares how cases are analyzed, how defenses are built, and how outcomes are pursued with precision and purpose.
Whether fighting in trial, negotiating a reduced charge, or guiding clients through the most difficult times of their lives, David shows exactly how his firm stands apart in the criminal defense field.
Key Moments in This Episode
0:45 – How technology fuels modern criminal defense3:20 – Why communication and client portals are essential5:10 – Evidence over allegations: David’s case evaluation process7:45 – The “cards in hand” metaphor for assessing state evidence10:15 – Leveraging AI and tools to strengthen defense strategies13:30 – Managing emotions and chaos in high-stakes cases15:20 – Defining real results: when trials vs. negotiations make sense18:05 – Why client trust is earned through transparency and diligence20:00 – Feedback from juries and clients as proof of impact
About the Show:
Defending the Windy City with attorney David Drwencke takes listeners inside the courtroom battles and legal strategies shaping criminal defense in Chicago and beyond. With years of experience as a judicial law clerk and criminal defense attorney, David shares real-world insight into protecting defendants’ rights, exposing flaws in prosecutions, and fighting for fairness in the justice system.

Tuesday Sep 30, 2025
Tuesday Sep 30, 2025
Episode Summary
In this first installment of a three-part series inspired by Simon Sinek’s Golden Circle, attorney David Drwencke, founding partner of DRD Law, shares the deeper purpose that drives his criminal defense practice. From childhood aspirations to a calling shaped by family values and years of courtroom experience, David explains why defending the accused is more than a profession—it’s a mission rooted in dignity, justice, and standing up against overwhelming odds.
Key Timestamps
00:00 – Why DRD Law Exists: David reflects on his lifelong calling to be an attorney and the personal values that fuel his passion for criminal defense.04:45 – The Golden Circle and Finding Purpose: How Simon Sinek’s “Start With Why” resonates with David’s vision of lawyering beyond making money.09:30 – Defining Justice in Criminal Defense: Why standing between the state and the accused is both a privilege and responsibility.14:20 – Believing Clients and Protecting Dignity: David discusses the importance of focusing on what can be proven, not just allegations.18:10 – The Human Side of Clients: How understanding clients as fathers, mothers, spouses, and children shapes his defense approach.20:00 – The Core Why of DRD Law: Every client deserves dignity, defense, and a trusted advocate to stand with them through the toughest moments of their lives.
About the Show:
Defending the Windy City with attorney David Drwencke takes listeners inside the courtroom battles and legal strategies shaping criminal defense in Chicago and beyond. With years of experience as a judicial law clerk and criminal defense attorney, David shares real-world insight into protecting defendants’ rights, exposing flaws in prosecutions, and fighting for fairness in the justice system.

Monday Sep 08, 2025
Monday Sep 08, 2025
Episode Summary
In this episode of Defending the Windy City, Chicago criminal defense attorney David Drwencke, founding partner of DRD Law, unpacks one of the most common tactics used by prosecutors: overcharging. David explains how prosecutors often stack charges beyond what the facts support in order to intimidate defendants into plea deals or create leverage in negotiations.
Drawing on years of courtroom experience, David outlines why overcharging happens, how it affects defendants facing serious felony charges in Illinois, and what defense attorneys can do to push back. He shares real-world examples, including a case where a client charged with attempted murder ultimately pled to a far lesser offense after strong advocacy and negotiation.
This episode is a must-listen for anyone facing criminal charges or supporting a loved one through the process. David provides clarity on what overcharging really looks like in practice, the role of judges, and why having a fearless defense attorney is critical to ensuring fairness when the state overreaches.
Key Timestamps
0:09 – 2:11 — Introduction to overcharging and why prosecutors use it as leverage.2:12 – 5:12 — The difference between probable cause and proof beyond a reasonable doubt.5:12 – 8:45 — Case example: breaking down an overcharged attempted murder.8:45 – 12:36 — What clients and families should understand about top-level charges.12:36 – 15:38 — Why defense reputation matters and how to pressure the state instead of the client.
Show Description
Prosecutors often charge defendants with the most serious crimes possible, not because the evidence supports it, but to create fear and leverage in negotiations. In this episode, criminal defense attorney David Drwencke explains how overcharging works in Cook County, what charges are most often inflated, and why it’s essential to have the right defense attorney to push back.
Drawing from real-life cases, David breaks down how prosecutors use aggravated charges like attempted murder or aggravated battery and why defendants shouldn’t assume their future will be determined by the initial charging document. Listeners will gain valuable insight into how strong advocacy, trial readiness, and strategic negotiation can counter prosecutorial overreach.

Friday Aug 22, 2025
Friday Aug 22, 2025
Episode Summary:
In this episode of Defending the Windy City, criminal defense attorney David Drwencke, founding partner of DRD Law, discusses the hidden problems in police investigations. David explains what a thorough and unbiased investigation should look like, and contrasts it with the reality of investigative shortcuts, blinders, and confirmation bias that often lead to wrongful charges. He discusses how defense attorneys identify flaws in police work, from ignored witnesses to missing video evidence, and why body cams, surveillance footage, and even Ring doorbells can make or break a case. David also addresses the trust juries place in police testimony, how that perception has shifted in recent years, and shares real-world cases where pointing out investigative weaknesses turned the tide in favor of his clients.
Key Timestamps:
00:01 – Show introduction01:15 – What a complete and unbiased police investigation should look like04:20 – The most common investigative flaw: blinders and confirmation bias08:05 – How defense attorneys spot red flags in discovery and reports12:10 – The role of body cams, pod cameras, and license plate readers16:30 – When missing or unpreserved video becomes a powerful defense argument20:15 – Do juries automatically trust police testimony? The reality today25:40 – Case example: a flawed sexual assault investigation and missing verification31:10 – Case example: body cam footage contradicts officer testimony in a gun case36:20 – Why defense attorneys must challenge investigative shortcuts at trial39:00 – Closing thoughts and where to connect with David Drwencke
About the Show:
Defending the Windy City with attorney David Drwencke takes listeners inside the courtroom battles and legal strategies shaping criminal defense in Chicago and beyond. With years of experience as a judicial law clerk and criminal defense attorney, David shares real-world insight into protecting defendants’ rights, exposing flaws in prosecutions, and fighting for fairness in the justice system.

Monday Jun 16, 2025
Monday Jun 16, 2025
Episode Summary:
Attorney David R. Drwencke discusses common misconceptions about marijuana legalization in Illinois, covering possession restrictions, transportation requirements, DUI implications, and expungement opportunities. He provides practical advice for avoiding legal issues and insights into how law enforcement handles marijuana-related cases.
Key Timestamps:
00:09 - Introduction and episode overview
01:02 - Common misconceptions about marijuana legality
06:09 - Marijuana-related convictions and expungement opportunities
09:18 - Mistaken arrests and how to avoid legal pitfalls
12:57 - Law enforcement handling of marijuana-impaired driving
15:34 - Future of marijuana legislation and testing methods
About the Show:
Defending the Windy City features experienced criminal defense attorney David R. Drwencke, who is committed to defending individuals accused of crimes in a passionate and non-judgmental way. Hosted by Abigail Vaca, the show provides valuable legal insights and practical advice for navigating the criminal justice system.

Monday May 26, 2025
Monday May 26, 2025
Episode Summary:
In this episode, experienced criminal defense attorney David R. Drwencke discusses the complexities of drug charges in Illinois, from misdemeanors to serious felonies. He explains defense strategies, recent changes in drug laws, and how the legal system approaches different types of drug cases.
Key Timestamps:
00:09 - Introduction and episode overview
00:36 - Types of drug charges and their severity levels in Illinois
03:20 - How prosecution builds drug cases and defense strategies
08:40 - Impact of changing local and state laws on drug defense
12:17 - Approach to drug trafficking and distribution cases
16:08 - Effects of evolving drug laws and marijuana legalization
About the Show:
"Defending the Windy City" features experienced attorney David R. Drwencke, who has dedicated his career to criminal defense. The show explores various aspects of criminal defense law, with David sharing his expertise and insights in a passionate and non-judgmental way. Hosted by Abigail Vaca.

Monday May 05, 2025
Monday May 05, 2025
Episode Summary:
In this episode of Defending the Windy City, host Abigail Vaca and criminal defense attorney David R. Drwencke discuss Chicago's new program allowing police to directly file gun charges without prosecutor approval. They explore the implications for due process, community relations, and civil rights protection.
Key Timestamps:
00:09 - Introduction and show overview
00:50 - Explanation of the new police charging program
03:10 - Discussion of risks to due process and accountability
05:20 - Impact on police-community relationships
08:02 - Legal implications and potential for biased charges
12:07 - Balancing efficiency with civil rights protection
15:40 - Role of prosecutor oversight
20:39 - Recommended checks and balances
About the Show:
Defending the Windy City features experienced attorney David R. Drwencke, who has dedicated his career to criminal defense. The show explores various legal topics affecting Chicago residents, with David providing insights from his extensive experience representing clients in a passionate and non-judgmental way.







