Behind the Eye Black: Charlie Szykowny

How Richmond's over looked infielder sprinted his way to professional baseball

June 26th, 2026

Most players treat drawing a walk in a literal sense, with a slow stroll to first base. Charlie Szykowny treats it like a race, charging toward the bag as if the game depends on beating a throw that’s never coming.

In an age of colored accessories, bat flips and choreographed dances, Szykowny’s style is one of an under-sized and under-rated kid from the Midwest.

“My dad would pull us from games if we didn’t run everywhere,” Szykowny said.

It was in those early days that Szykowny laid the “gritty player” groundwork he would later grow into.

Despite finding success on the diamond at Shepard High School, Szykowny stood just 5 feet 10 inches and weighed 160 pounds as a junior. His frame was considered undersized by recruiters, and he received little interest from college coaches.

“There wasn’t much, it was me emailing a bunch of schools and nobody responding.” Szykowny said.

During the summer, one of Szykowny’s local Midwest Havoc travel ball coaches connected him with a coach from the University of Wisconsin-Stout. The Blue Devils were one of only two schools to offer Szykowny out of high school, the other being Division III WIAC rival UW-Stephens Point.

After a productive Freshman year, playing in 16 games, Szykowny looked to take a leap in his sophomore season.

Instead, He played only three games before the season was cancelled due to the outbreak of COVID-19.

“It was a letdown for sure,” Szykowny said, “When the season got cancelled, we were literally about to pack the bus to go to a tournament in Florida.”

Szykowny, then 180 pounds, put all his attention into getting stronger for the 2021 season. The effort paid off, Szykowny gained 20 pounds and earned a role as a full-time starter in the Blue Devil infield.

Despite playing just 19 college games before his junior year, Szykowny kept believing.

“My wife thinks it's funny, when I started dating her I was like ‘Yeah I’m going to play professional baseball’ She kind of laughed at me, well, she didn’t laugh but she told me ‘yeah right, you’re playing D3,’” Szykowny said.

Szykowny broke out as a Junior, earning first-team All-WIAC honors. He ranked in the top 25 in the nation in hits and runs scored and set a school record with 22 doubles.

Since Szykowny had an extra year of eligibility due to the lost COVID season, he set his sights on finishing his degree at UW Stout and playing his final year at the Division I level.

But Szykowny was overlooked again. Despite a phenomenal year, there was no interest from high-major programs.  Like many college baseball players in his position, Szykowny went to the college summer ball circuit to draw more eyes to his game.

“I was like, I’m going to play summer ball and prove myself in those leagues,” Szykowny said.

Szykowny traveled to Batavia, N.Y., to play for the Batavia Muckdogs of the Perfect Game League. It was there that Szykowny said he learned how to hit for power, and after a short stint in the Northwoods League, he got in contact with coaches at the University of Illinois–Chicago and committed to the Flames before his Senior Year at UW-Stout.

Szykowny’s newfound power played a big role in his final year with the Blue Devils as the reformed slugger set a plethora of school records, notably launching 18 home runs. Finally, Szykowny received the recognition he had been chasing. He was named a second-team All-American by both D3baseball.com and ABCA/Rawlings.

He left UW Stout holding six school records and moved closer to home to play his final college year in Chicago. The production didn’t slow down at the higher level, Szykowny was named MVC Newcomer of the year and led the flames in home runs, hits and batting average.

Following his graduate season, Szykowny was selected in the ninth round of the MLB Draft by the San Fransico Giants.

“It was the best day ever” Szykowny said, “Once it happened it was the best, I had family members coming in, and people from the neighborhood just stopping by, it was like an endless party, It was great.”

Often overlooked, whether it was his size or schooling at Division III, Szykowny’s dedication paid off to accomplish his dream.

“It is definitely a big motivation tool, more than anything, proving not to yourself but to everyone,” Szykowny said, “D3 baseball players are good too, it’s a good league and everyone’s got good players.”

Today you can find Szykowny in the Flying Squirrels’ infield, still holding true to the always-hustle mentality instilled in him by his father in the sandlots in Palos Heights.

“Work harder than everyone and have fun playing the game because that’s when you learn how to play it. If you’re having fun playing the game, then you will want to work even harder,” Szykowny said.