CHICAGO -- Champagne toasts should be delivered by White Sox fans around Chicago at approximately 11 p.m. CT on Sunday.
It was at that moment on Oct. 26, 2005, when closer Bobby Jenks retired pinch-hitter Orlando Palmeiro on a slow roller to shortstop Juan Uribe to finish a four-game World Series sweep of the Astros. The White Sox ended an 88-year championship drought and closed out one of the most dominant postseason runs in Major League Baseball history.
As the Dodgers and Blue Jays battle for the ’25 crown, and as Chicago moves forward from its third straight campaign with at least 100 losses, the question arises as to how long it will take for the White Sox to get back to this desired level of competition.
That question was broached to Darrin Jackson, the astute radio analyst moving into his 27th season on White Sox broadcasts, albeit without knowing yet what the team’s offseason additions and subtractions may look like.
"I’m looking at three years. Three years is a team to me that you are saying now they are competing for the division, and who knows where it can go from there,” Jackson told MLB.com during a recent interview. “Next year the team is going to be competing to get close to .500.
"That’s why I look at the year after that you can build on the .500. [Then] you're saying, 'We have the pitching that has been here, they are established. We’ve got the players who have developed, and we have some players who we brought in, and I think we’ve got the staff, the manager, to make them intelligent players and cut down on their mistakes.'
"So, three years from now, to me, they are a team that’s in the playoffs."
Working as a television analyst alongside Hall of Famer Ken "Hawk" Harrelson before moving to radio for the past 17 seasons has allowed Jackson to study both the franchise’s greatest team in ’05 to baseball’s most single-season losses in the Modern Era in ’24. The 12-year veteran outfielder was impressed with the overall development shown by the ’25 team.
Jackson also used that ’05 championship crew as a goal for this current group to strive toward.
"There’s no Jermaine Dye. There’s no Aaron Rowand. We do have a [Luis] Robert. There’s no Scott Podsednik in left. There’s no Joe Crede at third base. There’s no [Tadahito] Iguchi. You look at Uribe,” Jackson said. “These were great ballplayers who had tremendous individual seasons, and they were great as a team.
“You're like, ‘That’s perfection, that’s how you build a champion. Everybody plays together as a team. You have great individual performances.’ You can build that within the next three years. I look it as a three-year range going into next year, so one, two and then the third year, you're going, ‘Here we are. We finally made the postseason. … We built, we were patient, and it shows up.’”
Look at the Dodgers' and Blue Jays' rosters. The White Sox don’t match up on paper against either of those teams, which have two of the game’s top 5 payrolls. Chicago isn’t quite there when looking at the Tigers, Guardians or Royals within the American League Central, either.
Then again, the White Sox aren’t designed to be there. Their '25 season featured the arrival and significant on-field exposure of shortstop Colson Montgomery, reliever Grant Taylor, catchers Kyle Teel and Edgar Quero and second baseman Chase Meidroth. A full upcoming season for that group -- as well as another full season for All-Star hurler Shane Smith, relievers Jordan Leasure and Mike Vasil and infielder Miguel Vargas -- alongside continued Minor League promotions gives general manager Chris Getz more opportunities to see where they need to add from the outside.
Yes, it’s an extended journey. But it's one Jackson believes fans understand.
"They saw that this team is going the right direction. They want to be part of that. I don’t think it’s hard to sell,” Jackson said. “I couldn’t be more pleased, to be honest with you. Sure, I would have loved for them not to lose 100-plus games. But you know what? It doesn’t matter. You’ve got to be excited about the direction this team is going because they play smarter, better, brighter baseball.
"I’m a baseball guy. I can see the direction the team is going. It really has to do with the front office and staff, first and foremost, that they know how to put a product together. … Why wouldn’t you want to be part of that growth with the team, part of that energy at the ballpark?"