Skip to main content

About me


Andy CherkaskyI knew I would be a trial lawyer as long as I can remember.  I was one of those kids growing up that loved to argue about everything and anything.  Parents, teachers, siblings, it didn’t matter — and the truth is, I won most of those fights.



I attended college at the University of Wisconsin in Madison.  My studies were all focused on the necessary course work to later attend law school.  During college I was the captain of the mock-trial team that won third in the nation.  I majored in political science, but I also had significant studies in computer science and film production.  My background in computers and film will give you an incredible advantage in your case.

In 2003 I began law school at Chicago-Kent College of Law.  While in law school, I focused my education on courtroom trial work.  Chicago-Kent is ranked in US News and World Report as one of the top three schools in the nation for courtroom training.  Within the first month of law school I was hand selected as the school’s top trial lawyer prospect.  I spent the next three years intensely training with one of the most highly regarded trial professors in America.  During that time I traveled nationally to compete on behalf of my school.  During law school I was put on scholarship for my role on the trial competition team (much like an NCAA blue-chip football player).  I was formally certified the top in my class in trial advocacy during my second year.  I also contributed to the authoring of a revolutionary book titled Litigation Technology.  Like I said, that computer and film background is a huge tool for us to use in your case.


Court-Martial Lawyer

I graduated law school in 2006 and immediately passed the Illinois bar exam.  I then commissioned into the United States Air Force and attended Officer Training School at Maxwell AFB in Alabama.  The Air Force didn’t pay for law school or college.  I joined for many of the same reasons as everyone else — I was inspired by my two grandfathers’ service, and then became dedicated to serving after 9/11.


After OTS, the JAG Corps sent me through a 9-week intensive tech school with over 70 other new JAGs.  I graduated from tech school and was given the award for being the number one litigator.


My first assignment was Aviano Air Base in Italy as a base level prosecutor.  Based on my skills and proven ability, I handled the base’s most serious and complex cases.  Cases ranging from drugs, to sexual assault to homicide.  My name and reputation as the best young trial lawyer started to circulate throughout the Air Force.


After only two years, I was promoted to be the local military defense counsel at Aviano.  This is the same position held by your assigned free military defense counsel — known as an Area Defense Counsel in the Air Force.  Within 3 months I handled the Air Force’s most high profile case — a previously convicted child pornographer that escaped from Air Force jail in England and went on the lamb for almost a year.  The case was front-page news in London.


Complex cases began to pour into my office, and I began to rack up impressive statistics for having cases dismissed prior to trial, acquittals at trial and for light sentences in cases where my client plead guilty.  After just over six-months on the job, I was recognized as the Air Force’s top CGO defense counsel.


Just as quickly as I started my work as a defense counsel, the Air Force decided to “promote” me again.  I was reassigned to an Air Staff position in Washington D.C. as a senior prosecutor (STC).  There are only about a dozen STC positions worldwide and I became one of the most junior captains to ever hold the position.  My job was simple; I was dispatched on a moment’s notice, worldwide, to prosecute the most complex, high profile, and serious offenses in the Air Force.  I was TDY almost 200 days per year, handled over 20 cases a year, and won almost every case I had.


I was named the first Special Victims Unit prosecutor upon the direction of the Secretary of the Air Force.  Amid growing criticism of how the Air Force handled sexual assault cases, I was specifically chosen asthe person that would handle sexual assault cases.

During my tenure, I tried cases at over 40 bases CONUS, in Europe and Asia.  I had a jury trial almost every other week.  I tried almost every kind of case, to include: drug use, white-collar larceny, child pornography, sexual assault, rape, and murder.


Brass in DC recognized my abilities as the best in the business, but I began to grow increasingly wary of the abuses I witnessed by command, investigators, and lawyers.  The military has a unique ability to unreasonably prosecute and destroy the reputation, careers and liberties of those falsely accused of crimes.  In my entire tenure in the Air Force, I didn’t witness a single policy change that increased the rights or protections to the defendant by those in power.


Over a year ago, I dropped my papers, refused a personal invitation from The Judge Advocate General of the Air Force for a position in the reserves and decided to dedicate myself to fight the abuses of the Air Force.  The Air Force may have wanted me to be their top litigator and poster-prosecutor, but Cherkasky Law is dedicated to truly Defending America’s Heroes.


Photos and videos

1095225 1391215628

1095225 1355256514

Practice areas


  1. Military Law: 41%
    9 years, 200 cases
  2. Criminal Defense: 39%
  3. Violent Crime: 15%
  4. White Collar Crime: 5%



Hourly ($225-275/hour), Fixed (sometimes), Retainer (always), Free consultation (60 minutes)

Payment types:

Cash, Check, Credit card

Attorney endorsements

7 total 

Are you an attorney? Endorse this lawyer

  • David Carl Beyersdorf

    I endorse this lawyer.


    David Beyersdorf Criminal Defense Attorney
    Relationship: Fellow lawyer in community

  • Mark V. Clay

    I highly endorse Mr. Cherkasky. Very knowledgeable and caring attorney who produces great results in representing clients! I want all people with legal problems to contact him first.


    Mark Clay Immigration Attorney
    Relationship: Fellow lawyer in community

Contact info

Cherkasky Law, LLC

2626 Lakeview Dr. #1408
Chicago, IL, 60614



ILActive And Authorized To Practice Law200611/12/2015
We have not found any instances of professional misconduct for this lawyer.
Avvo contributions
Legal answers
Award nameGrantorDate granted
CGO Defense Counsel of QuarterUnites States Air Force2010
Best LitigatorAmerican Association for Justice, New Lawyers Division2007
Work experience
TitleCompany nameDuration
OwnerCherkasky Law, LLC2012 - Present
Senior Trial CounselU.S. Air Force2007 - 2012
Association namePosition nameDuration
American Association for JusticeMember2007 - 2008
Legal cases
Case nameOutcome
US v ParrottN/A
United States v. CMSgt BowserDismissed with prejudice
United States v. SSgt MarshAcquittal of all litigated charges and minimal confinement for guilty plea charges
See all legal cases 
Publication nameTitleDate
Flex Your RightsDoes the Constitution apply to rights of military members?2013
Aspen PublishersLitigation Technology: Becoming a High-tech Trial Lawyer2006
School nameMajorDegreeGraduated
Chicago-Kent College of Law Illinois Institute of TechnologyLawJD - Juris Doctor2006
University of Wisconsin, MadisonPolitical ScienceBA - Bachelor of Arts2003
Speaking engagements
Conference nameTitleDate
Trial Advocacy ConferenceLitigation of Sexual Assault2012
Tournament of ChampionsTrial Advocacy Tournament Honored Guest Judge2012