Judge Ann Clare Oakar - The Person Behind the Robe

By Ed “Flash” Ferenc

Not too many children know what they want to be when they grow up.  Judge Ann Clare Oakar was an exception and her journey to become a judge is clearly one worth noting.

Judge Ann Clare Oakar

Growing up, what’s your favorite memory? 

I think my favorite memory growing up is Christmas mornings.  I have five siblings and for much of my childhood, my siblings were away at school but Christmas morning, we were all home together.  Us younger siblings would drag them out of bed and we would all head downstairs to see what Santa brought.  We usually would make some sort of breakfast and then in the afternoon, my extended family always came over to celebrate.  Of course we look back at life with rose colored glasses but it always seemed to be so joyful.

You realized you wanted to be a lawyer at a very early age—five years old.   What prompted that and did you share your goal with others, including the kids your age?

My father is an attorney and I spent a lot of time working or just tagging along to his law office.  I remember one particular time he was in the middle of a several week long civil jury trial.  My mom brought us down to watch.  The judge literally hopped off the bench to meet us, he was so down to earth and personable.  I fell in love with the whole experience. 

At 10 years of age, you spent time at your Dad’s law office.  What did you do?

Sometimes my sisters and I would just hang out while my dad went over files or met with clients and as I got older, I would fill in for when his secretary was out of town or sick.  I would answer the phones, type up letters or motions and sort mail.  We would go out to lunch, sometimes with my oldest siblings who now worked downtown.  I loved tagging along to court and seeing him in action. 

Can we talk about your Aunt, Mary Rose Oakar?  Her days on City Council, State Legislature and then the halls of Congress.   Can you reflect on that time?   Did you travel to Washington to see her and if so, did that experience change you in any way?  What struck you the most about DC?

My aunt won her seat in Congress literally the year I was born.  It was all I ever knew.  I remember going to rallies and fundraisers for literally my entire life.  I always felt like she was making a difference and how important that was to do with your life.  I didn’t realize when I was young what an amazing jetsetter she was, I didn’t know she was the first at so many things.  To me, she was just my Aunt Mary Rose.  When she would come in town, my whole extended family would meet at the Brown Derby by the airport.  I remember my little sister and cousins sitting under the table sneaking the half and half cups while the adults chatted above us.  We always were allowed to get Shirley Temples as our drink for these special occasions. 

We did visit her in Washington D.C. and she took us all around onto the house floor and into her office.  My dad had gone to law school in D.C. so it was familiar to him as well. 

As I have gotten older, I am shocked and amazed at not only what my aunt has accomplished but also my dad and their other brothers.  My grandfather was from Syria, he barely spoke English.  My grandmother was first generation from Syria.  They were very poor.  But their values and faith were the foundation of their family and they instilled the importance of education and community involvement in their children.  My grandmother was a precinct committee member for her neighborhood.  My grandfather walked to work from Ohio City to Euclid some days to provide for his family.  I try to instill these same values in my own children and to live them every day.  I want to make a difference in my community and to better the lives of others which is why I ran for Judge in Cleveland.  I never let myself lose this mindset even on the toughest of days when I feel like I am not making a difference.  I hope that I better the lives of all those that live in Cleveland and beyond. 

You went to CWRU to study law.  Talk to me about that time—how difficult was it?    And when you found out you passed the bar, what did you do?

CWRU is a difficult school.  When I graduated it was within the top 50 law schools in the United States.  I was actually enrolled at Cleveland Marshall all the way until the beginning of August before my first year.  I was working at a summer camp and received a call from the Dean offering me a scholarship opportunity if I came to CWRU.  I decided to make the switch.  I had some hard days.  I remember calling my college advisor from the payphone in the lobby telling him I didn’t belong there.  Luckily he reassured me and I pushed through.  I feel fortunate to be a graduate of CWRU, I had amazing professors and was pushed to my intellectual limit.  I feel that I learned critical thinking and reasoning skills in law school and also it truly taught me how to write well. 

Passing the bar was such a relief.  I literally did nearly nothing besides studying for three straight months.  I was convinced if I didn’t pass that I couldn’t take the bar again because there was truly nothing more that I felt I could do.  At that time, you had to call in to get your results.  I remember living in an apartment with Deirdre on W. 110th Street and making the call.  I asked the operator to please repeat herself a few times to be sure it was real and then I am pretty sure I cried.

Your license to practice law finally arrived.  What was your first case?

I was working as a law clerk at the time at the Legal Aid Society, which was also the municipal public defender for our court.  My very first case was sitting second chair with an attorney, Joe Howard in a jury trial before Judge Zone.  Our client was a familiar one to most of the court.  He had 19 cases and clearly we cared much more than he did, as he barely showed up to any client meetings as we tried to prepare.  I think the jury split on a few charges but he was definitely found guilty of many.  Judge Zone took the prosecutors, the other defense attorney and myself to dinner afterwards.  I will never forget the cooperation between our office and the prosecutors and the Judge.  It again solidified my desire to be part of this community in Cleveland Municipal Court.  It took nearly 17 years but the dream was realized when I won election in 2017. 

You served as law director, prosecutor and magistrate in various communities.  Was that difficult to navigate all those roles?

I loved serving the cities that I worked for over the years.  I loved being an insider to how the cities and villages operated.  As a Prosecutor, I truly felt like I was doing good for both the victims of the crimes and even for the defendants.  I really wanted to make a difference and felt like I could impact the lives of those affected by crime.  As a law director things were sometimes tough.  Questions came up about things I had only briefly read about in law school.  Some days, I felt like a jack of all trades and a master of none.  It often was a lot of research and just going with your gut.  It was an amazing exercise in rational thinking and on the spot decision making.  Sometimes I felt too young to be in some of the roles but I usually was able to prove myself with correct analysis.  When I was lucky enough to be offered the position as Magistrate, I again felt young to be in the position.  There were many older attorneys who would come before me and it took a few months to gain confidence to keep my courtroom in order.  It was a perfect training ground for my current role as Judge.  I had extremely large dockets, 150-220 on any given afternoon.  Again, I had to think on the spot and move people through court in a timely manner.  I worked for three judges, so I also learned to navigate their different styles and preferences.  These three jobs along with managing and running my own private law office definitely prepared me for my job today.

Running for judge, was that a decision that took a lot of soul searching and what about your family, did they support you right away?

The timing was right to run for judge as there were many openings on the Court.  It took me a long time to make the decision because I had previously been able to navigate and manage my schedule while raising three young children and with a husband who was in a demanding job.  Again, my desire to make an impact on the community where I live and also my desire to get back to the Cleveland Municipal Court where I had started eventually made the decision. 

You’ve been a judge on Cleveland Municipal Court for five years now.   If there is one word (or two) to describe that experience, what would it be? 


Do you see the criminal justice system any different now after your experience on the bench? 

Not really, I always tried to analyze all sides of the criminal justice system and I was fortunate to have taken part in all three parts of the courtroom, prosecution, defense and as a magistrate. 

Raising children is not an easy task, especially if you’re working full time.   Talk to me about that adjustment in your life.

Raising my kids, is the greatest privilege in my life.  There is definitely a balance that takes place when you are working and have younger kids at home.  There is also a balance when you are a public figure and have young kids.  I try to shield them from those issues the best that I can.  At home, I am mom.  At their school, more often than not, I am called Mrs. Henry (my husband and kids last name).  In fact sometimes when I was on the ballot, I was worried people at school wouldn’t know it was me!  My kids are getting a bit bigger now and I really try to enjoy my time with them as much as possible.  I know these years are fleeting and they will be out of my house in a blink of the eye.  They will always be my greatest accomplishment. 

What do you like to do in your free time?  Any favorite vacation spot?  

My husband and I met working at a summer camp in Bath, Ohio.  I had camped there as a child and eventually began working their when I was 17.  He had friends working there and happened to apply a few years before me.  Our kids now go to resident camp there and together we attend a family camp each year as a family.  We have a network of friends that all worked together and also still continue to be involved.  It was a tough but fun job and the people we met there and the time we spend there is always special.  This is by far our favorite vacation.  It isn’t fancy, nothing crazy but good old fashion fun, outdoors, minus electronics and fun and contact with the outside world.  We are fortunate to be part of this family.

Favorite book, movie?  

I am not great at sitting still long enough to watch movies. My favorite book is the Notebook by Nicholas Sparks.  I first read it in college in a class called Perspectives on Aging.  It is a good old fashion cheesy love story with some sadness thrown in.  I think it will always be my favorite even as I age and become less of a romantic!

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