Welcome to the South Side Sports Roundup! Check back every month for the latest news and updates on everything South Side sports fans need to know.
South Sider of the Month: Antwaan Randle El
Though he’s technically a native of suburban Riverdale, just a southwards jump over the Calumet River away from West Pullman, Bears assistant coach Antwaan Randle El and the city of Chicago have no issues claiming each other. Randle El is poised to play a significant role within rising-star Ben Johnson’s second-year coaching staff, a once-in-a-lifetime opportunity to bring glory to the city and team he spent his childhood supporting.
A three-sport star in football, basketball, and baseball, Randle El is one of the more decorated alumni in Thornton Township High School’s history, a school in nearby Harvey that counts Chicago-area legends Lupe Fiasco and Melvin Van Peebles among its attendees. Despite being selected by the Chicago Cubs in the 1997 MLB Draft, Randle El chose to attend Indiana University, where he initially played baseball, basketball, and football before his stardom on the field led him to focus solely on football. With nearly 7500 passing yards over his four years in Bloomington, Randle El was the Hoosiers’ all-time passing leader for more than a decade, and remains in second place today. His nearly 3900 career rushing yards are also good for second in Hoosier history, as are his 44 rushing touchdowns.
After finishing sixth in Heisman Trophy voting as a senior, the Pittsburgh Steelers made Randle El a second-round NFL draft pick in 2002, converting him from quarterback to wide receiver in the process. His nine-year career in Pittsburgh, and later Washington, made him a fan favorite thanks to the trick plays made possible by his throwing abilities. He finished his career with 22 passing completions, the most ever for a player who never actually appeared at the quarterback position. In 2006, he became the first wide receiver to throw for a touchdown in a Super Bowl, an iconic game-sealing deep ball to secure a championship for the Steelers.
After his playing career, Randle El won another Super Bowl as an assistant coach for the Tampa Bay Buccaneers before joining the Detroit Lions as wide receivers coach. He now fills the same role for the Bears, with the added title of assistant head coach. Just as importantly, he seems to feel like he’s home.
“I growing up and watching the Bears, and rooting for them when I playing them,” he told the Chicago Sun-Times in 2025. “It’s always been a thing for me to get back here, and the way it happened … I’m excited, and I’m thankful.”
Do you have a pick for South Sider of the Month? Email our sports contributor Malachi at mzhayes95@gmail.com.
High school football teams gear up for fall
High schoolers in Chicagoland are getting ready to return to school at the end of August. But if they play football, they might already be kicking it on campus. Practices for the fall season are starting up across the city, and a number of schools are looking to keep the Chicago Public League championship trophy on the South Side.
Coming off a city title, the Morgan Park Mustangs kick off their campaign next week, hoping to become the first repeat champions since the Simeon Wolverines, who accomplished it in 2016 and 2017. The CPL title has made quite the home on the South Side in recent years, as the Wolverines returned to capture the title in 2019 and 2022, while the Kenwood Broncos took gold in 2021 and 2023. Since 2009, a non-South Side school has only held the title twice, most recently the Whitney Young Dolphins in 2024.
Having coached that Dolphins team to its first ever CPL plaque, Dan Finger knows what it takes to compete at the highest level. Though he hopes to get the near-West Side school back to the top in 2026, he recognizes that this road still runs through the South Side.
Finger told the Weekly that it “hasn’t changed all that much” since the early 2010s. “It starts with Morgan Park, for sure. Then Simeon and Kenwood are going to be right there,” he said. He also pointed to the King College Prep Jaguars as an up-and-coming program that could make noise.
There’s loads of great competition to be found in the CPL, but there are few high school conferences that boast the competitiveness of the Chicago Catholic League, which features a pair of South Side state champions from 2025 in Brother Rice and Mt. Carmel. According to Finger, “they’re one of the best conferences in the country, I’d say the best in the Midwest, top to bottom.”
Having come up short against Rice in last year’s Illinois High School Association Class 7A state championship game, coach Martin Hopkins and his St. Rita Mustangs squad are hungry for another chance to hang a banner in their home gym.
“Our guys had a chance to see what it takes to get to [the championship], and now they have a perspective. They know the amount of work that goes into it, and they’ve been working all offseason,” Hopkins said.
Beyond wins and losses, Hopkins is also enjoying the relationship-building aspects of coaching youth sports. Now in his fourth year running St. Rita’s program, after taking over from longtime coach Todd Kuska, he looks forward to watching the season play out with the first group of graduating seniors he’ll have spent a full four years with.
“It’s exciting to see. [It’s] funny, looking back, I remember them as eighth graders. [It] feels like it was just last week,” he said. “It’s cool to see what they’ve done in their short time [at St. Rita], and I’m excited to see what they do this year.”
High school football games across the state begin the weekend of Friday, August 21. The conference schedule for the CPL begins on Thursday, September 10.
Bears set to open preseason schedule versus Cleveland
After two weeks of training camp, the Bears are set for their first preseason bout with the Cleveland Browns, slated for Saturday, August 15 at Soldier Field. The game will mark the beginning of what may be the most highly anticipated season.
The Bears are coming off a year that saw them shatter all pre-season expectations, capturing their first division title since 2018 and engineering a thrilling playoff comeback against the Green Bay Packers during the National Football Conference Wild Card Round in January. Though they’re not favored to take home another NFC North title, they’re widely expected to be serious playoff contenders.
Lifelong Bears fan Brandon Miller, of South Shore, is feeling optimistic about their trajectory.
“I’m feeling really positive. They made a lot of strides last year,” he said. “I’m confident in Ben Johnson’s ability to lead the team as well as Caleb [Williams], so I’m excited. Hopefully they get a couple more wins out of it this year.”
A couple more wins to top off the 12 they posted last year, including playoffs, would likely put them firmly in Super Bowl contention. Unfortunately, their championship aspirations have already taken a blow, as starting safety Coby Bryant is expected to miss eight to ten weeks due to a knee injury he suffered in practice on August 3. Bryant was signed to a three-year, $40 million contract in the offseason after the departure of both regular safeties from the 2025 season.
Other key players have reportedly experienced minor injuries of varying degrees, including running back Kyle Monangai, edge rusher Montez Sweat, offensive lineman Braxton Jones, and wide receiver Luther Burden. Starting cornerback Kyler Gordon remains on the physically unable to perform (PUP) list with a calf injury.
Despite the injuries, fans of other NFC North teams are wary. Hyde Park resident Ian Daly, who hails from Minnesota and considers himself both a Vikings and Bears fan, told the Weekly that “the Bears look like the best team in the North if they don’t choke.”
On a positive note, the Bears ensured star tackle Darnell Wright will be a long-term fixture on the offensive line, signing him to a record-seeing four-year, $116 million extension. Additionally, quarterback Caleb Williams has reportedly looked good in practice time, as have wide receiver Luther Burden III and tight end Colston Loveland.
Daly believes that Loveland is a player to watch after the 2025 first-round pick emerged as a star late in the season. Miller believes that Monangai, who ran for 783 yards and five touchdowns last season, is poised to make a star turn this coming year.
The confidence in the Bears isn’t universal. Longtime fan Emmanuel Noelliste, of suburban Crestwood, is bearish on the Monsters of the Midway.
“They lost key pieces and that will require Caleb to be a force multiplier for this to work,” he said. Many believe that Williams is on the verge of leaping into the highest tier of NFL quarterbacks, but Noelliste cites his tendencies to “hold the ball too long” and “miss easy throws” as factors that will hold him back.
We’ll get the first look at Williams’ third campaign with the team on Saturday. Starting players typically play no more than one or two drives to open the preseason, but it’ll nonetheless be the first live Bears action in nearly seven months. Some fans are hopeful that it could also be the first look at a true new era in Chicago football.
“Chicago finally has a real quarterback instead of a discount quarterback and a great defense,” Miller said. “This is a different pace and a different team, and I’m really excited for that.”
Sky remain out of playoff picture
WNBA All-Star weekend has come and gone at the Wintrust Arena and the United Center, and the Chicago Sky’s future remains bleak. They entered the week with a 12-21 record, good for 11th place in the league. At seven games behind the eighth-place Dallas Wings in the standings, a playoff berth is all but out of reach, and with Washington Mystics owning swap rights to their first round draft pick, no immediate help is on the way.
On the brighter side, undrafted and unheralded guard Sydney Taylor has emerged as a breakout star, averaging 18.8 points per game on nearly 49% shooting since entering the rotation full-time on June 17. In what will be a critical offseason for coach Tyler Marsh and general manager Jeff Pagliocca, re-signing the former Louisville and UMass star could become a priority for the Sky this winter.
White Sox make deadline moves
The White Sox made a number of small moves, and one notable splash, in advance of the Major League Baseball trade deadline on Monday, August 3. It’s their first time in a half-decade as clear-cut “buyers,” as teams around the league either waved the white flag or loaded up on reinforcements with just under two months remaining in the season.
Their headline acquisition was three-time All-Star starting pitcher Luis Castillo, who came from the Seattle Mariners in exchange for reliever Seranthony Domínguez, outfielder Nolan Jones, and prospect Boston Smith. Castillo is an electric player but has struggled this season, allowing five runs in five innings in his Sox debut.
The Pale Hose also traded minor leaguers in exchange for outfielder Brenton Doyle from the Colorado Rockies, relief pitcher Huascar Brazobán from the New York Mets, and catcher Joey Bart from the Atlanta Braves.
They remained in first place in the American League Central division entering this week, holding a three-and-a-half game lead over their Detroit rivals and Cleveland, and a four-game lead over Minnesota, with a little over a month and a half to play.
Malachi Hayes is a Bridgeport-based writer and South Side native.