South Side Sox: for Chicago White Sox fans

It's that time of year again (again), but so much has changed: Rather than being a team just hoping to spoil the other's season, as was the case back in May, the White Sox have ascended into first place and in fact sit in significantly better postseason position than the crosstown Cubs. Malachi Hayes, Brian O'Neill, Leonard Gore, Chrystal O'Keefe and Brett Ballantini assemble to preview this week's series, but quickly descend into crapping on the Cubs insipid franchise, hackneyed mystique and clownish fans. Learn more about your ad choices. Visit megaphone.fm/adchoices

Katie Dzwierzynski joined Chrystal O'Keefe to chat about the upcoming Crosstown Classic series at Wrigley Field against the Cubs. Katie provided updates on the trade deadline and her optimism with the rest of the 2026 season for the Cubs. Despite Milwaukee's division lead, Katie still thinks the Cubs can make a push, and the two pondered how the city will handle both teams in the playoffs. Chrystal and Katie previewed the series, going over pitching matchups, this time with four new pitchers getting a crash course in Crosstown shenanigans. Before wrapping up, Katie shared her hopes and fears, and gave a few hot takes. Learn more about your ad choices. Visit megaphone.fm/adchoices

After the weekend sweep of the latest pretender to the AL Central crown, the Detroit Tigers, it felt like the right time to try to figure out what in the world is going on with our Chicago White Sox. And attempting to solve that delicious riddle are Chrystal O'Keefe, Brett Ballantini, Malachi Hayes, Brian O'Neill and Leonard Gore. Team Southpaw faced off against Team Pope Hats to dig into the surprisingly solid core of the White Sox and vibe check our confidence levels in the White Sox finishing the job and winning the division. Learn more about your ad choices. Visit megaphone.fm/adchoices

Ashley, the co-host of American League with Ashley and Motor City Metrics, who also contributes to Tigers ML Report and became a certified MLB Scout last year, joined the show to talk about all things Detroit Tigers. With the American League Central up for grabs no lead is safe, and that is exactly what Chrystal and Ashley started with. The two talked about the trade deadline after Detroit dealt Tarik Skubal and Casey Mize, and how it was still successful for the Tigers. The pair also previewed the White Sox series, with Ashley sharing the keys to winning and what she's afraid of. Before ending the show, Chrystal and Ashley talked about the potential lockout, Ashley's predictions, and how inclusivity matters in all sports, especially baseball. Learn more about your ad choices. Visit megaphone.fm/adchoices

Wick Terrell of our sister site Red Reporter is back this season to talk all things Red. After a lackluster trade deadline and a lot of injuries, Wick's high hopes of the Reds having a good season have dissipated. Wick and Chrystal talked about what's new with the Reds and previewed the series — with keys to win, fears, and that speedy Elly De La Cruz. They also were reminded of Eloy Jiménez undergoing emergency surgery in Cincy, theorized on if Marge Schott and Pete Rose cursed the Reds, and how wonderful Joey Votto is. Learn more about your ad choices. Visit megaphone.fm/adchoices

Mikayla Baer joined Chrystal O'Keefe to talk about all things Guardians, including what's new in Cleveland (spoiler alert: it's most of their players), how she feels about the trade deadline, and the rest of the season. She also talked about her card collection and her joyous first trip to Rate Field. The pair discussed pitching matchups, keys to winning the series and just getting runs in with runners in scoring position. Before closing, Mikayla and Chrystal chatted about their fears with a lockout looming and how we really need a salary floor. Learn more about your ad choices. Visit megaphone.fm/adchoices

Ed Hand is back to chat about the Red Sox. In this episode Ed talked about his trade deadline hopes for Boston, and how they've been red-hot since right before the All Star break. He and Chrystal previewed pitching matchups that changed mid-episode, talked about keys to winning and fears, and shared a lot of David Sandlin love. Before wrapping up, the pair talked about the possible work stoppage and why the Dodgers sometimes ruin everything. Oh, and more emo music. Sorry. Learn more about your ad choices. Visit megaphone.fm/adchoices

Joe Kiang-Resis, Malachi Hayes and the reformed, refurbished and revitalized Leonard Gore gathered together with Brett Ballantini to talk over the four moves made at the trade deadline by the White Sox, from good to ... puzzling. By the end, we speed-rounded grades for Chris Getz's first "buying" deadline, as well as whether or not Cleveland and its acquisition of Foster Griffin had a better deadline session than the White Sox. Learn more about your ad choices. Visit megaphone.fm/adchoices

Minors writers Melissa Sage-Bollenbach and Joe Kiang-Resis hop on with Brett Ballantini to take a pause from our monthly reviews and discuss the events of the day. Talk of SSS Player of the Month for July Boston Smith, now departed to Seattle, triggered a discussion on whether it was the right time for the White Sox to be using prospect capital to ensure the postseason in 2026 (answer: yes). We spun that into some yes/nos on trades that were rumored but did not happen: Smith and George Wolkow to New York for Freddy Peralta, and Braden Montgomery to Baltimore for Adley Rutschman. Finally, we peered into the crystal ball and predicted the two September call-ups to the White Sox. Learn more about your ad choices. Visit megaphone.fm/adchoices

Jason Collette, of FanGraphs and Rotowire, is back to talk about the Tampa Bay Rays. Jason addressed Tampa's trade deadline needs, and how to get by the pesky Yankees and Red Sox, who still find ways to win. Jason and Chrystal talked about pitching matchups for the coming series, and the pros and cons of opening pitchers in previewing the series. They also lauded the ABS system, issues with catchers, cool bobbleheads, and how sometimes sports hurt your feelings. Learn more about your ad choices. Visit megaphone.fm/adchoices

Asher from Pitcher List made his season debut to talk about all things Yankees. He discussed what's new, including an Aaron Judge health update, what the Yankees need to do at the deadline, and how confident he feels about playoff chances. The duo previewed the series and talked about their mutual love of weird pitchers and Jason Benetti. Learn more about your ad choices. Visit megaphone.fm/adchoices

Andy Brown is back this season to talk about the Houston Astros. For the first time in more than a decade, the Astros will likely be sellers at the trade deadline, in an everything-must-go situation. But even still, there is some hope for the franchise. Chrystal and Andy previewed the series and talked about the great vibes at Rate Field this season. Andy also shared his hot takes, including how baseball still needs to figure out how to grow the game. Learn more about your ad choices. Visit megaphone.fm/adchoices

Levi Weaver, co-writer of The Windup with Ken Rosenthal on The Athletic, joined Chrystal to talk about all things Rangers. Before digging into what's going on in Texas, Chrystal asked about Levi's Halloween costume from last year: George Pee-Wee Herman Ruth, which he put together for his Sandlot baseball league. The pair discussed what is needed at the Trade Deadline and how unserious the American League is this year before previewing the upcoming series. Before closing, Levi shared a few baseball takes before diving into an emo debate and praise of seeing Nick Cave live. Learn more about your ad choices. Visit megaphone.fm/adchoices

Do women still have to prove they're "real sports fans?" On this episode of Ladies' Night, hosts Melissa Sage-Bollenbach and Kristina Airdo are joined by Dakota Rouse from the Chicago Women's Sports Club to talk about gatekeeping, finding your community, and why sports are better when everyone feels like they belong. Learn more about your ad choices. Visit megaphone.fm/adchoices

Melissa Sage-Bollenbach, Dante Jones and Malachi Hayes hopped on with Brett Ballantini to discuss the fabulous first half for the White Sox, but more so to focus on the second half and stretch run that could give the club its first postseason berth in five seasons. We discuss how the second half plays out, who ends up winning the division, what the trade deadline will look like, who finishes the season as the White Sox MVP — and much more! Learn more about your ad choices. Visit megaphone.fm/adchoices

Former voice of the Toronto Blue Jays, current Toronto Star baseball columnist and host of the Deep Left Field podcast, Mike Wilner joined Chrystal to chat about the Blue Jays. Mike discussed what's new with the Blue Jays, and why he's not feeling negative about the team. The two also previewed the upcoming White Sox series and talked about what Mike is enjoying this season, as well as the statue being unveiled soon. Learn more about your ad choices. Visit megaphone.fm/adchoices

Chrystal O'Keefe, Brian O'Neill and Hannah Filippo hopped on with Brett Ballantini to discuss the fabulous first half for the White Sox, but more so to focus on the second half and stretch run that could give the club its first postseason berth in five seasons. We discuss how the second half plays out, who ends up winning the division, what the trade deadline will look like, and who finishes the season as the White Sox MVP — and much more! Learn more about your ad choices. Visit megaphone.fm/adchoices

It was a little hard to tell at South Side Sox given all of our normal draft features being churned out, but this year marked a wrinkle to our coverage: Actual writers on the ground to cover the event. Melissa Sage-Bollenbach and her son, Sage, were in Philadelphia for the draft, Melissa as credentialed SB Nation media. Now ... did that turn out to be a good thing? And did Sage, donned in a UCLA Roch Cholowsky jersey and White Sox cap, get feasted on by writers and broadcasters looking for No. 1 overall draft choice material? Tune in to learn all of the the ins, outs and power failures of the weekend experience in Philadelphia, as the pair sits down with Brett Ballantini to chat on MLB draft 2026. Learn more about your ad choices. Visit megaphone.fm/adchoices

Melissa Sage-Bollenbach, reporting from the 2026 draft in Philadelphia, joined Brett Ballantini to wrap up an extremely impressive effort by the White Sox. We revisit the debate over the No. 1 overall pick (we had both settled on a player other than Roch Cholowsky), Chicago's maneuverings to land Landon Thome, note securing a first-round talent (and Grady Emerson doppelganger?) Cole Prosek at 41, and other highlights — including players taken DEEP in the draft, all the way down to Round 20. Learn more about your ad choices. Visit megaphone.fm/adchoices

The wonderful Aaron Cameron is back for the second time this season to talk about the Athletics. Aaron shared his experience with seeing the A's in Las Vegas, as they start to integrate and build hype in the desert. The pair went over trade deadline needs and confidence levels about 2026. Chrystal and Aaron also previewed the series, talked about the game they caught together at the end of May in Chicago, and Aaron shared his hottest take to date — he hates the Home Run Derby. Learn more about your ad choices. Visit megaphone.fm/adchoices

Red Sox media jack-of-all-trades Owen Brown made his Visiting Dugout debut to talk to Chrystal about what's new in Boston and preview the upcoming laundry series. Owen touched on the April firings, the Willson Contreras suspension, and if the Red Sox will be buyers or sellers at the deadline. The pair also went over what to expect in this series including pitching matchups and fears, before moving on to what's going on with MLB in general. Learn more about your ad choices. Visit megaphone.fm/adchoices

Imari McPherson joins again to talk about a familiar team, the Cleveland Guardians. While the pitching matchups in this series will be similar, the White Sox will see the Guardians on the road this time, and for four games. Learn more about your ad choices. Visit megaphone.fm/adchoices

The full squadron of South Side Sox minors writers (Brett Ballantini, Melissa Sage-Bollenbach, Joe Kiang-Resis, Kristina Airdo and Hannah Filippo) assembled to review June and the first half in the White Sox system. We assessed the second-half fortunes for each affiliate, and highlighted some of the system's brightest and most disappointing players. Learn more about your ad choices. Visit megaphone.fm/adchoices

Dream is back to talk to Chrystal about all things Orioles. The pair talked about what's going on in Baltimore, and previewed the series and what to expect. Learn more about your ad choices. Visit megaphone.fm/adchoices

If there's one thing you can count on from Sox Populi, it's that every time the White Sox win a game by 21, we'll be on the air for a postgame podcast. That's our promise. Of course, that's never happened in White Sox history, and there's been just one bigger blowout in all 126 years of play for the South Siders, also against a Kansas City team (the Athletics, in 1955). And the 22 runs scored in the blowout tie for the second-most ever by the team (again, 1955, 29 runs). Game recapper Trevor Land (in his Sox Populi podcast debut) and Hannah Filippo hopped on with Brett Ballantini to talk about the win. And believe it or not, one of the trio STILL is not overly impressed with this White Sox team. Find out who, and give us a listen. Learn more about your ad choices. Visit megaphone.fm/adchoices

Journalist Vince Guerrieri joined the podcast to chat with Chrystal about the Cleveland Guardians. Plagued with injuries and losing the heart of the order, the Guardians are still lingering at the top of the American League Central alongside the White Sox. Vince talked about the offseason, and how Cleveland owners don't spend money on free agents, either, as well as his confidence levels for taking the division. The pair previewed the series, and the pitching clinic the Guardians always seem to have. Vince shared the keys to winning, and his fears heading into the series before breaking away and sharing his insight on the rest of the season and the potential labor stoppage in 2027. Learn more about your ad choices. Visit megaphone.fm/adchoices

Chris Brown of Motor City Metrics and Tigers ML Report is back to chat about all things Detroit Tigers. Chris went over what's new, and not-so-great this season as well as his picks for the All-Star Game (Spoiler alert: He voted for Colson Montgomery over Kevin McGonigle) Chrystal and Chris went over pitching matchups, fears heading into the series, and keys to winning. Then talked about Chicago's magical year, and how the division could certainly be for the White Sox to control. Learn more about your ad choices. Visit megaphone.fm/adchoices

Raise your hand if you thought we'd be talking about a first-place White Sox team in mid-June. Yeah, us either. Join the Ladies' Night crew as we discuss the biggest surprises, breakout stars, and what's next for the South Siders. Learn more about your ad choices. Visit megaphone.fm/adchoices

It's the "It's a Miracle!" edition of Sharing Sox, as duty geezer Leigh Allan and his son and usually west coast (but currently second bedroom, as he's in Chicago for the critically-acclaimed production of An Enemy of the People at TimeLine Theatre) correspondent, Will, celebrate the incredible season the White Sox are having so far, which includes just having taken series from both the Braves and Dodgers. They rave about just about every player and even manager Will Venable, and — get this — avoid saying anything at all about Jerry Reinsdorf as they consider just how long and far the wonderfulness can last. Learn more about your ad choices. Visit megaphone.fm/adchoices

Dan Epstein of Baseball Prospectus joined Chrystal to talk about all things Yankees. Dan talked about the ever-present injury bug in the Bronx, the offseason, and how confident he is about the Yankee's playoff chances. The two also spent a lot of time talking about how pitchers are the coolest, and how our old friend Carlos Rodón has changed since his time on the South Side. Learn more about your ad choices. Visit megaphone.fm/adchoices

Eric Stephen, co-host of Three-Inning Save Podcast and ruler of all things True Blue LA, joined Chrystal to chat about the Los Angeles Dodgers. Eric talked about what's new with the Dodgers, including injuries, bullpen depth, and what happened in the offseason. The pair went over pitching matchups and what to expect in the series, as well as how nice it is to see Miguel Vargas thriving. Before ending, Eric shared his thoughts on the potential stoppage of next season and how he envisions everything happening. Learn more about your ad choices. Visit megaphone.fm/adchoices

The White Sox were in first place by percentage points via Cleveland loss earlier in the day, but the Sox Populi crew of Brett Ballantini, Chrystal O'Keefe and Melissa Sage-Bollenbach were going to make the team earn a celebratory postgame podcast with a win over vaunted Atlanta — and win they did, 2-1, moving a full half-game into first. It's the first time the White Sox have been in first place past April 15 since 2022, and the first time atop the division in a meaningful way since 2021. The trio spoke of the surprises of the season, favorite players to watch — and fears, if any, lurking on the road ahead. Learn more about your ad choices. Visit megaphone.fm/adchoices

Demetrius, the managing editor from our sister site, Battery Power, joined Visiting Dugout to chat about the Atlanta Braves. With a new manager, and strong pitching and offensive firepower, Atlanta leads the National League and seems to be firing on all cylinders. Demetrius shared what is going right, and how he is taking things one day at a time. There will also be a lot of old friends back for the series, as the White Sox will see Chris Sale and Martín Pérez. Before wrapping up, the pair talked about how players like Munetaka Murakami are good for growing baseball. Learn more about your ad choices. Visit megaphone.fm/adchoices

It's the end of the month, so that means it's time for some of the South Side Sox minors crew to band together and talk about the system. In this episode, Brett Ballantini, Joe Kiang-Resis, Melissa Sage-Bollenbach and Hannah Filippo discuss the South Side arrival date of Braden Montgomery, the resilient Cannon Ballers, Jacob Gonzalez's rise, and many more minors nuggets. Learn more about your ad choices. Visit megaphone.fm/adchoices

Mitch Bernstein is back on Visiting Dugout to chat about the Phillies. Mitch and Chrystal talked about his fandom over the years, who makes baseball great, and what is happening in Phillies land. They also talked about the series and what to expect from pitching matchups, and how unknown pitchers look like Cy Young winners when facing the Phillies. Learn more about your ad choices. Visit megaphone.fm/adchoices

Rogelio Castillo joined the podcast to talk with Chrystal about all things Tigers. He tried to explain what is happening in Detroit, with injuries and early season struggles, but sometimes baseball is just an enigma. The pair previewed the series, and how it's do-or-die for the Tigers heading into June. Before wrapping up, Rogelio and Chrystal talked about the possible labor stop next season, and what baseball needs to do to actually grow the game. Learn more about your ad choices. Visit megaphone.fm/adchoices

Britt Huber made her fourth appearance on the podcast. Next time she's on, I'm going to have to ask Saturday Night Live where they order their Five-Timers Club jackets. The ladies talked about all things Giants, with what's new, how the offseason went, and confidence levels in a cut-throat division. They talked about how Buster Posey will never escape his playing days despite being the President of Baseball Operations now. The duo also previewed the series, talking about all things pitching and what to expect. To conclude the episode, they talked a bit about the joys and pitfalls about discovering more about players, why inclusion matters, and Pete Crow-Armstrong crossing the line with his words. Learn more about your ad choices. Visit megaphone.fm/adchoices

Sara Sanchez from Bleed Cubbie Blue returned to chat about the first Crosstown series. Sara talked about what is new with the Cubs, and what is currently working for the team. Chrystal and Sara also previewed the series, the Cubs curse of 2016, and one year of the Chicago Pope and what he's doing right. Oh, and a tailgate mass. Learn more about your ad choices. Visit megaphone.fm/adchoices

Michael “Lux” Farina is back on to chat about all things Royals. Chrystal and Michael chatted about the rough start for the Royals, the great city connect jerseys, and how odd this season has started off. They also previewed the series, including pitching matchups and keys to winning the series. Learn more about your ad choices. Visit megaphone.fm/adchoices

The Ladies' Night crew is back to recap the White Sox's first-ever Gameday for the Girls event at Rate Field. From interactive fan experiences and women-focused activations to meaningful conversations about representation in sports, we break down our biggest takeaways from an evening dedicated to celebrating women in baseball and sports media. Join us as we discuss the atmosphere, the VIP panel, our favorite moments from the night — and why events like this matter. Learn more about your ad choices. Visit megaphone.fm/adchoices

Claire Jones is back this season to chat about the Mariners. While there is some hope for Seattle, Claire expressed her frustrations with what's going on with the injury-prone team. Claire and Chrystal previewed the series and what to expect from pitching, and ended with a conversation about the potential lockout in 2027. Learn more about your ad choices. Visit megaphone.fm/adchoices

Nearly the entire minors crew at Sox Populi (Brett Ballantini, Joe Kiang-Resis, Melissa Sage-Bollenbach, Hannah Filippo) got together to discuss the first month of the affiliate seasons. Top news was the day's big development, getting word that Braden Montgomery was headed to Triple-A. Otherwise we took a team-by-team look at the season so far, highlighting the other bests of the best (Caleb Bonemer, Colby Shelton, Rikuu Nishida, Jackson Kelley, and many others). Learn more about your ad choices. Visit megaphone.fm/adchoices