Back on May 8, the Cubs were 27-12 and riding their second 10-game winning streak, while the White Sox were 17-21 and hoping to get to .500.
But the Cubs went into a free fall as the Sox started winning and gaining confidence. Through Thursday, the Sox (33-29) have passed the Cubs (33-30), a 10-game swing in less than one month. Will this “Freaky Friday”-style switch continue, or will both teams revert to preseason expectations?
Every Friday during the regular season, Tribune baseball writers will provide an update on what happened — and what’s ahead — for the Cubs and White Sox.
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Cubs’ Ian Happ collects 1,000th career hit
Cubs left fielder Ian Happ is safe at second base with a double as Athletics second baseman Jeff McNeil takes a throw during the ninth inning Wednesday, June 3, 2026, at Wrigley Field. (AP Photo/David Banks)
Ian Happ has a deep appreciation for Cubs history and the players who came before.
So when he stood on second base after a hustle double in the fourth inning Wednesday at Wrigley Field, Happ took in the scene. Fans gave Happ an ovation in recognition of the left fielder collecting his 1,000th career hit, all with the Cubs. Happ, the longest-tenured current Cub, tipped his helmet to the crowd in acknowledgement.
Afterward, Happ described what made the moment memorable, particularly to do it at Wrigley.
“Being with this team for as long as I have, wearing this uniform, representing the city and the Ricketts family and the tradition of what’s here,” he said. “And the fans have given me so much here. That’s the most special part is that every day they’re here, they’re supportive.
“So to do it with one team, to do it over the course of my career here, that’s what makes it really, really cool.”
Happ, 31, became the the 37th player in Cubs history to reach the milestone and only the second switch hitter, joining Don Kessinger (1,619 hits).
One of Happ’s first thoughts when he reached second base for No. 1,000 was remembering his first major-league hit in 2017: a home run at Busch Stadium. Every other Cubs player who appeared in that game played for them during the 2016 World Series championship season.
“There was never a time when I didn’t think I was going to be in the big leagues or with this team,” Happ said. “Certainly to come up with the guys that I did and that group of individuals, players who’ve accomplished so much in the game, and to watch the way that they played and went about their business and the things that they’ve achieved and then to kind of continue that on here.
“I played with guys that have set some crazy records here, and you look at like everything that (Anthony Rizzo) did here and then to be able to be on some of those lists, it’s special to me. It means a lot.”
No. 1 pick part of ‘exciting time’ for Sox
UCLA’s Roch Cholowsky hits a sacrifice fly against Saint Mary’s in the fifth inning of an NCAA regional game May 29, 2026, at Jackie Robinson Stadium in Los Angeles. (Keith Birmingham/Pasadena Star-News)
All eyes are on the White Sox with the top pick in the 2026 MLB draft. There has been plenty of speculation they could go against the flow and choose someone other than UCLA shortstop Roch Cholowsky, the consensus No. 1 pick since last winter.
But no one knows for sure except Sox general manager Chris Getz and director of amateur scouting Mike Shirley. (OK, maybe they whispered the plan to Chairman Jerry Reinsdorf).
Getz, speaking Monday in Minnesota, wasn’t about to show his hand.
“There’s more than just the first pick,” he said. “You’ve got 20 picks and undrafted free agents that are part of a draft. We feel we have a pretty good sense of where things are and getting organized.
“It’s an exciting time for the White Sox, not only because of what we’ve been able to accomplish so far, but get a chance to add that level of talent with the first pick is something you don’t always get to do.”
Getz said it’s a huge investment, so he tries to sit down with and get to know the players and their families and coaches personally.
“You want to make sure the quality of the person is right, with being associated with the talent they have,” he said. “I’d say that’s one of the biggest reasons I go out and try to see the top talent.”
MLB Pipeline polled 21 members of the scouting industry to rank the class and predict the top pick. Cholowsky was selected as the top player by 13 of the 21, while Georgia Tech catcher Vahn Lackey got six votes. High school shortstops Grady Emerson from Texas and Jacob Lombard from Florida received one vote apiece.
“Roch has separated himself as a near-ready major-league shortstop,” one scouting executive told MLB.com. “He bet on himself going to college, and it paid off. I’d be shocked if by the end of 2027 he’s not in a big-league uniform.”
As for whom the Sox would pick, Cholowsky was the overwhelming favorite with 15 votes, followed by Emerson (three), Lombard (two) and Lackey (one). Cholowsky’s top-seeded Bruins were upset on the first weekend of the NCAA Tournament, depriving Sox fans of a chance to see him play in the College World Series in Omaha, Neb.
Getz said the current state of the Sox doesn’t matter to the pick, though Cholowsky seemingly would be more major-league ready than a high school player. Shirley’s first pick as scouting director — Tennessee pitcher Garrett Crochet — was the No. 11 selection in 2020. Crochet was brought up late that season and made five relief appearances, though it was under unusual circumstances during the pandemic year.
Number of the week: 31
Sox reliever Grant Taylor’s strikeout total in 20 1/3 innings over 15 appearances. He has an 0.89 ERA.
Week ahead: Cubs
Cubs designated hitter Moisés Ballesteros takes batting practice before a game against the Athletics on Wednesday, June 3, 2026, at Wrigley Field. (AP Photo/David Banks)
Friday: vs. Giants, 1:20 p.m., Marquee
Saturday: vs. Giants, 1:20 p.m., Marquee
Sunday: vs. Giants, 7:30 p.m., NBC-5
Monday: off
Tuesday: at Rockies, 7:40 p.m., Marquee
Wednesday: at Rockies, 7:40 p.m., Marquee
Thursday: at Rockies, 2:10 p.m., Marquee
Most of Moisés Ballesteros’ playing time continues to come at the designated hitter spot.
The Cubs, though, continue to look for opportunities to get him time behind the plate. Ballesteros started at catcher in Thursday’s series finale against the Athletics with left-hander Shota Imanaga on the mound. It was only the fifth time he has caught this season — the first in three weeks — and just his third start there.
“Pitching matchup for the other team, we put a lot of lefties in the lineup,” manager Craig Counsell explained, “and I think that’s the best way to go against this pitcher (J.T. Ginn), try to beat the starter early in the game. So that’s kind of where we landed on that.”
Counsell previously paired Ballesteros with right-hander Colin Rea and left-hander Matthew Boyd. It’s not a coincidence that two of Ballesteros’ starts have come when the Cubs started a lefty who can better control the running game. Ballesteros’ defense remains a work in progress.
“Our lefties are so good at it,” Counsell said of keeping runners close. “It’s basically who we have pitching and who they have pitching.”
Week ahead: White Sox
White Sox shortstop Colson Montgomery hits a home run in the seventh inning against the Tigers on May 31, 2026, at Rate Field. (Eileen T. Meslar/Chicago Tribune)
Friday: at Phillies, 5:40 p.m., CHSN
Saturday: at Phillies, 3:05 p.m., CHSN
Sunday: at Phillies, 12:35 p.m., CHSN
Monday: off
Tuesday: vs. Braves, 6:40 p.m., CHSN
Wednesday: vs. Braves, 6:40 p.m., CHSN
Thursday: vs. Braves, 6:40 p.m., CHSN
After three-plus years of rebuilding, the Sox begin one of the biggest stretches of the season with four consecutive series against quality clubs, starting this weekend in Philadelphia.
They return home Tuesday to start a three-game series with the best team in baseball — the Atlanta Braves — followed by the two-time defending champion Los Angeles Dodgers. Then it’s on the road again to play the New York Yankees.
By the end of that stretch, the Sox should know if they’re real contenders or just a young team on the cusp of contending down the road. It also might factor into what Getz does at the trade deadline, where he has said the Sox could be buyers.
“I know that I have stated it’s not about 2026, but this team is playing really good baseball,” Getz said. “And we know where we are in the standings, both within the division and the wild card. We’re monitoring it, and if there are opportunities to add to this, we have higher hopes than just 2026 because we want to have a continual winner here. But if there are chances to add to this group, we’re going to do it.”
What we’re reading today
Quotable
“This team has played very good baseball. That’s probably No. 1. I still think we’re a talented roster. We have a talented position player group that’s capable of producing stretches like that and producing offense that can be dominant, consistent. We aren’t doing it right now, but we’re certainly capable of it because we’ve shown it already this year.” — Counsell on why he’s optimistic the Cubs still can end up where they want to be at the end of the season