New Trier and White Sox alum Charlie Tilson builds new team, dives into youth development

The thought of graduates from New Trier and Maine South high schools teaming up may throw some for a curve, but a pair of star alumni from the rival high schools are stepping up to the plate to guide the next generation of ballplayers.

Former Major League Baseball players Charlie Tilson and Brian Schlitter recently joined forces to form Crosstown Baseball Academy, an organization devoted to developing young baseball players through personalized training and instruction.

Tilson, a former Trevian, and Schlitter, a former Hawk, connected during their time in 2022 with the Chicago Dogs, an independent professional baseball team out of suburban Rosemont.

The local duo had long offered training sessions in the area, but it wasn’t until recently that Tilson, during his one-on-one hitting and outfield lessons with athletes, noticed an increased demand for pitching sessions.

From there, the Wilmette native made a call to the pen, where he united with the former Maine South hurler to create Crosstown Baseball.

Branding the endeavor came to Tilson and Schlitter right off the bat, given their ties to rival schools. In addition to their opposing Central Suburban League South allegiances, they both also spent time with major-league rivals as Tilson played for the Chicago White Sox while Schlitter pitched for the Chicago Cubs.

Tilson then further put together the organization’s staff by adding Loyola Academy graduate Christian Friedrich, a left-hander who pitched in the big leagues with the Colorado Rockies and San Diego Padres.

Evanston High School graduate Jack Anderson, who pitched at Penn State University and was drafted by the Seattle Mariners, is also part of the Crosstown team, and so too are Anthony and Alex Calarco, two of the most accomplished New Trier hitters in recent memory, and several Northwestern University players.

“I hand selected this group because they’re not only great from a baseball perspective but they’re inspiring coaches as well,” Tilson told The Record.

“I’m fortunate to have such great guys who are really incredible (coaches),” Tilson added. “Their baseball knowledge is off the charts, but more than anything, these are coaches that really inspire kids and they take that seriously, so that’s really the ultimate goal.”

Leading off

Crosstown Baseball got officially up and running in late 2025, and the group held several large training clinics around Thanksgiving.

Tilson said the group’s hope was to offer one-off, all-encompassing clinics to “allow kids to be introduced to all the different areas” of the game, including pitching, infield and outfield defense, baserunning, and hitting.

Since, Crosstown Baseball has further broadened its horizons by recently offering more specialized sessions for players who may be interested in deeper instruction in one specific skill.

Dozens of local players came out Sunday, Jan. 11, to New Trier’s Winnetka campus for the latest Crosstown clinic. First- through third-graders participated in the first half, while junior high students took part in the second time slot.

Training Sunday largely focused on many of the game’s fundamentals while also emphasizing the importance of teamwork. Those lessons are just a few of the goals Crosstown Baseball hopes to instill in young athletes.

“Me and Charlie saw a very big need for teaching basic fundamentals and instruction, especially at the youth level in all areas,” Schlitter said, adding that “if we can just instill those basic lessons of the game, then (these players) are already a step ahead of other kids in their age range.”

‘It’s so important, and I feel so fortunate’

During his time in the major leagues, Tilson took note of how some of the sport’s greatest players kept their preparation rooted in the game’s fundamentals. It’s a lesson that has stuck with him — and it’s a message that Crosstown Baseball coaches hope to pass on.

“Truthfully, when I was playing at the highest level, I noticed the best guys really had a knack for keeping things simple,” Tilson said. “And we try to do that for these guys … allowing them to understand that if they can just do the little things correctly, their game will take off, but it starts with dominating the fundamentals.”

As an 18-year-old out of New Trier, Tilson was named the 2011 Gatorade Illinois Player of the Year and then drafted by the St. Louis Cardinals in the second round of the MLB Draft. He opted to sign with the professional organization and forgo a full athletic scholarship to the University of Illinois at Urbana-Champaign.

During the 2016 season, the Cardinals traded Tilson to his hometown team, the White Sox. Tilson debuted with the White Sox that same year, knocking his first career hit in August against the Detroit Tigers in his first major-league game. But, in the same game, the outfielder suffered a season-ending hamstring injury.

After spending some time with the big-league club in both 2018 and 2019, the White Sox optioned Tilson to the minor leagues, and he chose to become a free agent.

The former standout Trevian signed with the Pittsburgh Pirates organization in January 2020 prior to the onset of the COVID-19 pandemic. Tilson was released later that year, in large part due to the uncertainty of the MLB season given the pandemic.

Tilson inked a minor-league deal with the Philadelphia Phillies in 2021, giving the former second-round draft pick another swing at the majors. Before getting the opportunity with another big-league organization, Tilson spent time with the Long Island Ducks of the Independent Atlantic League and the Acereros de Monclova of the Mexican League

Now rooted back in his hometown, Tilson is eager to pass down his knowledge of America’s pastime and help the next era of ballplayers further their love for the game.

“It’s so important, and I feel so fortunate,” Tilson said of working with younger players. “I grew up where my brother took me outside every day and played with me and I want to share that same experience with kids, so they’ll continue to play and love the game.”

One of the essential lessons Crosstown Baseball aims to pass down, Tilson said, is “that if you love this game and you want to get better, the difference between where you are and where you want to go is practice.”

“And we try to make practice so fun and passion forward that they will want to go home and work on it themselves, I would say that is the number one goal,” Tilson added.

“Outside of that, we really want to hone in on the fundamentals and break down each step to allow kids to gain confidence, whether they’re just starting out or they’ve got a lot of experience and they need to be challenged. We’re prepared to meet both ends.”

In addition to his work with Crosstown Baseball, Tilson also served on the coaching staff of New Trier’s varsity baseball program last season, working with the team’s roster on hitting, defense and baserunning.

The Trevians great said he’ll continue to volunteer with the team as long as head coach Dusty Napoleon will have him.

“I absolutely love it,” Tilson said, adding that another goal of Crosstown Baseball is “continuity” with New Trier baseball.

“We want the younger kids practicing exactly the way that we’re practicing at the varsity level,” Tilson said. “I think we look four, five, six years down the line as these kids start high school, this could be really impactful and that’s something I’ve talked to Dusty about and that’s what really makes me excited about this opportunity.”

Those interested in learning more about Crosstown can visit the organization’s website or reach out to Tilson at Charlie@charlietilson.com.

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