The common narrative surrounding the Chicago White Sox in the second half of 2025 has been their pursuit of 63 wins — or, to be more precise, avoiding a third straight 100-loss season.
One hundred is a nice, round number that easily lends itself to media narratives. It’s the 100th anniversary of something that gets attention, not the 99th or 101st. In baseball annals, a 100-loss season is proof of a horrible year, though it’s really no different from a team that loses 98 or 103 games.
Regardless, 99 was the bizarro magic number for the Sox, and achieving it theoretically would validate the moves made by general manager Chris Getz and his front office, showing that the rebuild is progressing at a fast clip and a turnaround is in sight.
For a while it looked like it would happen.
The Sox started out 10-4 after the All-Star break but then lost six straight and 14 of 17 to revert to factory settings. After another five-game losing streak left them 40 games under .500, 100-plus losses seemed inevitable again. An 8-2 start to September raised hope anew before a current six-game losing streak dampened the optimism.
Now the Sox need to go 6-3 over their final nine games to finish with 99 losses, and they face two teams vying for postseason seeding in the San Diego Padres and New York Yankees.
Photos: Chicago White Sox lose 3-1 to the Baltimore Orioles at Rate Field
The quest continues Friday night on the South Side when Dylan Cease and the Padres come to town for a three-game series at Sox Park. The stirring video tributes to Cease and Gavin Sheets will coincide with the Padres left-hander facing Davis Martin in Friday’s opener.
Giveaways will be front and center. The Sox slogan should be: “Come for the cool stuff, stay for the baseball.” A guayabera Friday, a St. Paddy’s hockey jersey Saturday and the crème de la crème for Sunday’s home finale: a 1959 Comiskey Park radio that originally was scheduled for June 28 but got pushed back because of production delays.
The same, of course, could be said for the Sox rebuild. Production delays marred the first half of Year 2 of the Getz plan, but things have improved offensively since the call-up of shortstop Colson Montgomery on the Fourth of July.
No, he’s not a savior and he still needs to cut down on strikeouts and prove he’s better at short than third base or even right field. But there’s no doubt the Sox desperately needed Montgomery’s power and persona. If this Sox core is to progress in 2026, Montgomery will have to be its “designated Rizzo,” a star who effortlessly deals with the media and fans.
Montgomery’s success makes one wonder whether Getz made too hasty a decision in spring training, when the top prospect was sent back to minor-league camp after he started late because of back spasms and went 1-for-9 in Cactus League games.
That’s not much of an audition, especially when your choice to start at short was Jacob Amaya. What would Montgomery’s stat line have looked like had he started the season in Chicago? Would they still be 13-33 in one-run games?
That was just one decision by Getz that’s overlooked in the rush to proclaim the Sox rebuild a success because of a 20-or-so-game improvement over the worst season ever. His most important trade will be fruitful if outfield prospect Braden Montgomery arrives in 2026 and Kyle Teel develops into an All-Star, which seems quite possible. But Garrett Crochet is a Cy Young candidate in Boston, and the White Sox need both to become stars to justify that trade.
Remember, Getz had three key assets to trade when he came on board: Cease, Crochet and Luis Robert Jr., who remains with the Sox only because his trade value became microscopic. Getz’s first big move was dealing Cease to the Padres during 2024 spring training for four players: Drew Thorpe, Jairo Iriarte, Samuel Zavala and Steven Wilson.
White Sox general manager Chris Getz answers questions during a news conference before a game against the Orioles on Wednesday, Sept. 17, 2025, at Rate Field. (Eileen T. Meslar/Chicago Tribune)
Thorpe has been out all year after Tommy John surgery, Iriarte has a 7.00 ERA and 1.93 WHIP at Triple-A Charlotte and Zavala is still at Class A Winston-Salem. Wilson has been a solid reliever in his second season with the Sox, but the trade appears lopsided considering the Padres got two seasons of Cease in his prime.
When Cease and the Padres were at Wrigley Field in April, I asked him why the Sox never seem to re-sign their starting pitchers.
“I guess it’s just an organizational philosophy type of thing,” he said. “They’ve had a lot of really good talent.”
That “organizational philosophy” is not paying their starters market value and having to trade them for prospects before they leave via free agency.
“It seems like there are some teams willing to do almost anything and some teams that don’t want to do (as much),” Cease said. “I don’t know all the financials, which teams are run well and which ones aren’t. But for me, personally, I have nothing against teams that go all-in all the time. I don’t think there is any negative to that. At least other teams keep their star players.”
The 2026 Sox rotation remains unknown, other than Shane Smith and Martin, who cost next to nothing. Picking up Martin Perez’s $10 million mutual option is the kind of move the Sox like to make for payroll reasons — and to avoid paying a frontline starter on a long-term deal. Perez is a good guy but can’t be counted on to stay healthy.
Getz doesn’t seem eager to jump into free agency, which suggests the much-rumored “Ishbia bump” — a payroll increase with future owner Justin Ishibia’s wallet helping out — isn’t happening. The Sox will plead for more patience, and plan some more cool giveaways.
I was going to suggest Free Tattoo Night, only to have the Sox beat me to it. I received an e-mail from the Sox about a chance to enter a drawing to “receive a custom White Sox-themed tattoo, designed by celebrity tattoo artist Ryan Henry.” It did not say whether “Sell the team” is an acceptable tattoo or whether a tattoo of Tattoo from “Fantasy Island” wearing a Sox uniform would suffice.
At the reimagined SoxFest in January at the Ramova Theatre, director of player personnel Gene Watson boldly told fans the Sox front office would be recognized as “the best” in the major leagues when all was said and done. Sox fans booed loudly, knowing it was way too soon to crow after a 121-loss season. The 2025 season provided few clues that the front office is elite.
Will Watson repeat his boast at SoxFest ’26?
Tune in, or tune out.