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Tim Anderson: Mr. South Side

The All-Star Chicago White Sox shortstop is making a name for himself in Chicago by embodying the city’s swagger — and addressing its systemic issues.

Dating back to the heyday of Michael Jordan, Chicago has been home to hoop dreams quite literally. From the famed 1994 documentary to the revered rise of Derrick Rose, basketball’s been the city’s calling card for united interest and escape from its harsh realities.

Growing up in Tuscaloosa, Alabama, Tim Anderson idolized MJ like many a kid enamored with sports. Born the same day Mike dropped 44 points in the 1993 Finals, he was beginning to crawl the same time No. 23 was hanging up his sneakers in favor of attending batting practice. Over the course of his Alabama ascent as a promising prep athlete, the kid from Tuscaloosa and the pride of the Windy City would live juxtaposed narratives.

Rob Tringali/MLB Photos via Getty Images

Unlike Mike, Anderson would not outgrow his ancestry, reaching just over six feet of height as an amateur guard. Leaving Little League as a teenager in favor of hooping with his friends, the Hillcrest High School student gave baseball a second chance as a junior, batting .333 after years away from the diamond. By his senior season, he upped his average to .420 while helping the Patriots’ basketball team take home a state championship.

With his heart on the hardwood, the 6-foot-1 guard garnered junior college offers in both basketball and baseball. Set on joining the backcourt at Itawamba Community College 100 miles away in Fulton, Mississippi, he held out until the 11th hour and chose diamond dreams instead. Departing for Decatur, Mississippi, he enrolled at East Central Community College, where he batted .360 as a freshman and stole 30 bases.

And while statistics suggested he made the right choice, scouts didn’t see enough. After going undrafted, he exploded in his sophomore season by batting .495 — the single best nationwide mark in the junior college ranks.

With only four seasons of amateur baseball under his belt, the Chicago White Sox went on to Anderson 17th overall in the 2013 MLB Draft. Despite focusing on hoops for the better part of his life, the same squad that took on Michael Jordan in his infancy had handed him a signing bonus worth over $2 million.

After three years of figuring it out in the minors, the White Sox called up Anderson in 2016. In a matter of months, the South Side Sox knew they had their guy in TA, signing the shortstop to a $25 million contract extension in 2017. The same year all his hard work on the diamond was finally paying off, tragedy struck close to home in Alabama.

On May 7, 2017, childhood friend Branden Moss — he and Anderson eventually became godfathers to each other’s children — was shot and killed. In attempting to break up a bar fight in an attempt to help a man who just been beaten up, gun violence stole a friend, a father, and a fiance.

Like Anderson, Moss played high sports at Hillcrest and clearly cared about assisting others.

Like Tuscaloosa, Anderson’s new home of Chicago was no stranger to careless firearm-driven casualties.

“I had a close friend get killed by gun violence,” Anderson told Boardroom. “I took it upon me to keep his name alive and do something positive in the community for the kids. Obviously, with gun violence, especially being in the city of Chicago, I think it was the right fit.”

Since the passing of Moss, Anderson has made it his mission to have fun on the diamond while taking care of his community around it. Soft-spoken, Anderson is a man of few words, but many friends. At his recent TA7 Sneaker Ball at AceBounce in Chicago, teammates, and legends from the White Sox franchise showed up to support Tim through fun and fundraising in an event aimed at uplifting and protecting the youth in both cities he calls home.

“The idea for the Sneaker Ball came about just brainstorming, trying to think of something that would be really dope for the city,” Anderson says of the event backed by both Nike and his ball club. Benefitting League of Leaders — the foundation Anderston started in memory of Moss — the shoe fits where Anderson’s involvement is concerned.

Tim Anderson batting on Jackie Robinson Day at Guaranteed Rate Field in Chicago (Ron Vesely/Getty Images)

Across Chicago, fans flock to Bulls and Bears games if affluent enough to afford tickets. Where baseball is concerned, the Cubs are the stuff of corporate club seats and young professionals living life in Wrigleyville. Conversely, the White Sox speak to the city’s South Side, more known by comparison for a blue-collar work ethic and adverse living conditions. When Googling ‘South Side of Chicago,’ the next suggested search term is ‘crime.’

Since starting League of Leaders, Anderson has been praised for his ability to empower local youth through resources, advocacy, and harm reduction. A two-time All-Star, lucky No. 7 post highlight reels soundtracked by the late King Von while tweeting motivational messages akin to those seen on the feeds of Ja Morant and Lil Baby.

It’s not an act or script; it’s simply a franchise finding a star player that embodies electric play on the field with a cultural cachet off of it.

Because of his image and athleticism, the local youth has a link to America’s game that most markets miss out on.

“It’s been different,” Anderson said of the unique connection. “A lot of kids have been coming out and enjoying the games. To be able to see someone so relatable makes it a lot more cool.”

Famous for bat flips and clubhouse celebrations, Anderson aims to leave it all on the field while still meaningfully depicting who he is off of it. “I just try to give them a show,” he said. “If they come to see me play, why not play as hard as I can?”

Despite rehabbing a torn hand ligament, Anderson packed the AceBounce venue with famous faces ranging from Bo Jackson to Shermann Dilla Thomas.

Both the two-sport superstar and urban historian have carefully honed insights on just how the city reveres its athletes and just how much giving back matters to the local youth. Years ago, Derrick Rose revealed that his fanfare for Michael Jordan growing up was as much about his airborne accolades as it was the fact the Bulls games brought the South Side inside to stop the shooting outside.

In play and in philanthropy, Anderson is making it a mission to influence and assist Chicago kids just like him. He doesn’t make a show out of it because it’s a matter of personality, not production.

“Just really tapping into the culture,” Anderson begins when explaining how he got so at home in his second home. “Being in a city that’s so relatable to where I’m from definitely makes it a lot easier to connect the dots.”

Like Anderson, many kids on the South Side dream of ascending to the NBA as an escape from circumstances, they didn’t choose. While Anderson himself didn’t choose a life on the diamond until the summer after his high school graduation, it chose him just as the city of Chicago has.

“Baseball stuck,” Anderson admits. “I wasn’t 6-foot-6 [and] going to the NBA, so I stuck with baseball.”

But even at the top of his field, he’s still aware of the stigma and barriers that make the sport inaccessible for those that grew up just like him.

“It’s expensive when you’re younger. A lot of people can’t afford it, so the start is making it easier to transport kids to games and even the equipment,” he said.

With League of Leaders, however, Anderson can forge a charitable path toward decreasing gun violence and affording opportunities for the next generations to follow in his footsteps, and with the first annual Sneaker Ball, he can elevate his passions and his personality in a way that’s utterly authentic.

Working with Nike, the White Sox, and his wife, Bria, the festivities were able to bring in backers for one specially-selected cause while keeping things fun the whole way through.

Unafraid to be himself in a sport where he’s seen as an outlier, Tim Anderson has doubled down on staying true and giving back. Because of that, he’s made a home for himself in Chicago’s South Side, where’s he revered by teammates and local youth the same. As both cities that claim him face issues on the mound and in the trenches, he’s answering the call from Tuscaloosa to Lake Michigan with equal parts athleticism and activism.

However, when asked to choose his top five favorite sneakers at his charitable gala, he softly shudders.

“That’s a tough question,” Anderson smiles.

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