Inside Pitch: Introducing Our Newest Blogger Madison Winkler, the Fastest “Pickle” You’ll Ever See!

Madison "Pickle" Winkler has great speed and looking impressive this fall with the Lady Sluggers. She's also gone 47-for-50 in steals in her first two years of varsity high school softball.

At Extra Inning Softball, we love to give the athlete a chance to share her voice, insights, successes and even set-backs when it comes to the journey through the sport.

Today, we introduce you to a 5-foot-4 speedy outfielder named Madison “Pickle” Winkler who’s a 2022 grad at Christian County (Hopkinsville, Kentucky) where she’s been a varsity high school player since the 7th grade and has benefited by playing on the same field as one of the top 2019 grads in the country, Emmy Blane--a Univ. of Kentucky signee--who was in the Top 40 of the recently released Extra Elite 100.

The pair helped lead the Colonels to a Regional title and 5th place in state and Pickle over her first two years of varsity ball  has batted .456 with a .562 on-base percentage and gone 47-for-50 in steals while scoring 91 runs.

Pickle, who was starting to get interest from Big Ten and SEC schools before the Early Recruiting rules went into effect, also plays with Emmy on the Louisville Lady Sluggers 18U coached by Jim Huecker and works out regularly with older teammates going to D1 programs like Louisville, Kentucky, Florida State, Wisconsin, Tennessee and more.

This fall, the Kentucky freshman hit over .400 against elite competition playing the outfield and second base. She also went to the OnDeck Midwest Elite camp where she impressed with her speed, running a 2.81 (after being clocked at 2.7 in an SEC school’s camp) and recorded a 91.10 Allister Index score.

More than just numbers, however, is her impressive drive and passion to improve her game and do what it takes to make it in the sport she loves. We’re excited to chronicle Pickle’s upcoming season in high school and club and where the recruiting ride takes her.

So let’s cut to the chase and learn just where this talented athlete got her unique name and became the promising player she is today!


“Your name is what? You mean like the food?”

Yes, my name is Pickle. Well, technically, my name is Madison Winkler, but no one calls me that except my grandparents.

Now, I know you’re thinking… why Pickle? The day I was born, my clavicle broke and I swelled up and had all these little dimples all over me. My dad looked at me and started calling me Pickle and I have been Pickle ever since.

Pickle and top 2019 shortstop Emmy Blane helped the Christian Co. (Kentucky) Colonels take 5th at state in 2018.

I like it, it’s different, and most people will remember a girl named Pickle.  I am from Crofton, Kentucky, which is near nowhere you may have heard of, but it’s about an hour and a half from Nashville, Tennessee.

I play for Christian County High School and the Louisville Lady Sluggers-Huecker, but more about that later.  I want to tell you about my journey through this sport we love: softball.

From the time I was a baby, my older siblings played softball and baseball. I can’t remember a time when I wasn’t at a ballpark. I loved watching them play and would cheer from the bleachers as they would hit and run the bases. I couldn’t wait to play on the field like them, so as soon as I was old enough, my parents signed me up.

To be honest… I wasn’t very good, but I was fast so I was quickly picked up when I was six-years-old by a local travel ball team. The coach told my parents “I can teach her how to throw and catch, but you can’t teach speed.”

And so, my story began.

I played with that team--the Little Lady Colonels--until I was 12. I can’t tell you how much I learned from my first coaches, they were very supportive and taught me the fundamentals that led to me learning to slap and be able to play many different positions.

By around 12, I knew I wanted to play college ball so I had to make the decision to leave my first team and move to the A circuit. My first A team was the L’il Saints from Clarksville, Tennessee. Moving to the A circuit was a real eye-opener for me; I hadn’t seen pitching like that before, but it was so much fun that it was easy to not be discouraged.

That year, we played in the Sparkler, Jr, Inaugural USA Elite Select WFC, and ASA Nationals, where we placed 7th. I could not have been more proud of the way our team came together at the end of the season. Due to school ball that fall, I had to find a new travel team.

The 2022 grad has played with several local and national club teams, each helping improve her skills and add experience to her game.

At the Packaged Deal camp, my dad met someone from the Comets organization out of Alabama, and I went to a tryout and made the team.  Although I was an ‘03, and the team was an 02, I felt completely comfortable with the girls and especially the coaches.

My coach, Glenn Bradley (who is no longer with us), left me with a lot of knowledge that helped me on an off the field. One of my favorite things that he said was “Finish stronger than you started.” Every day, every practice, I try to keep his memory alive by living those words.

In August of this year, I tried out for the Louisville Lady Sluggers. In the tournaments I have played in, the Sluggers teams were always highly competitive and I like that home base is in Kentucky. When I made the team, I was offered a spot on the 18U team, so I decided to forego my two years of 16U and move up.

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