Editor's note: This story originally ran on April 18. Since then, things have indeed gotten bleaker for the White Sox. This story has been updated with Chicago's historic losing streak.

Just three years ago, the Chicago White Sox were the darlings of Major League Baseball. They were coming off an AL Central title in 2020, with an ascending core under club control and an executive of the year in Rick Hahn running the show. The arrow was pointing up on the South Side, with World Series aspirations and hopes for a long window of contention.

Today, the White Sox (27-88) are the worst team in baseball.

On Monday night, they lost their American League record-tying 21st straight game, a 5-1 defeat to the Oakland Athletics. Chicago's skid tied the 1988 Baltimore Orioles, who began the season 0-21. The 1961 Philadelphia Phillies own the MLB record of consecutive losses with 23 straight.

“We knew that it was going to be a challenge to play consistent winning baseball. And I say winning in terms of a wins and losses standpoint,” general manager Chris Getz told Yahoo Sports in April. “It’s just the reality of it: A lot of things have to work in our favor.”

Things have definitely not worked in Chicago’s favor this season. After a 101-loss season last year, the Sox got off to a miserable 3-16 start to 2024. The team’s offense started historically bad, averaging two runs per game and the White Sox were shut out in seven of their first 19 games.

Before the 21-game losing streak, the White Sox suffered through a 14-game skid between May 22 and June 6.

One of the points of emphasis under manager Pedro Grifol was supposed to be for his team to be fundamentally sound and do the little things well. That didn't materialized in the early going, with missed cutoff throws, uncompetitive at-bats and mental mistakes. There has already been a team meeting to discuss the collective performance and sloppy play.

“I just think guys are pressing,” Grifol said of the team's early-season struggles. “They really care. They want to turn this around. They want to produce and be a part of the solution and part of the turnaround.”

The farm system and the draft won't provide immediate help

To add insult to injury (or, rather, the other way around), Eloy Jiménez, Yoán Moncada and Luis Robert Jr. — the team’s three best players to begin the season — each suffered an injury while running to first base within the first 10 days of the season, sending them to the injured list. Moncada hasn't played since April 9 and Robert missed about a month. Jiménez was eventually traded before the deadline to the Baltimore Orioles.

Those early absences made the Sox’s lack of talent at the highest level even more apparent, leaving a roster in serious need of overhaul.

In an attempt to bolster their minor league ranks, along with Jiménez, the White Sox dealt: Tanner Banks, Paul DeJong, Michael Kopech, Erick Fedde and Tommy Pham. The returns on those deals included: relievers Trey McGough and Jarold Rosado, infielders William Bergolla, Alexander Albertus and Jeral Perez, and outfielder Miguel Vargas.

A majority of the team’s previous “core” — a group that included José Abreu, Tim Anderson, Jake Burger, Dylan Cease, Zack Collins, Lucas Giolito, Reynaldo López, Nick Madrigal and Carlos Ródon — is gone. The pieces that remain are oft-injured and haven’t lived up to anywhere near the expectations once set for them. And this void isn’t limited to the big-league level. Unlike most teams that lack significant talent in the big leagues, the White Sox’s farm system doesn’t contain the type of high-end talent to help expedite a rebuild. According to MLB Pipeline, Chicago’s farm system — which was the best in baseball by the end of 2017 — ranked 20th prior to the trade of Cease to the Padres.

Making matters worse, since the last time the White Sox were rebuilding — when they brought in the likes of Moncada, Jiménez, Robert and even Michael Kopech — changes to the CBA and the institution of the MLB Draft lottery have ended the days of the worst teams in baseball being guaranteed the top picks in the draft. No longer does tanking lead to instant blue-chip prospects such as Adley Ruschman, Bobby Witt Jr. or Paul Skenes.

Instead, the highest the White Sox can draft in 2025, regardless of their record this season, is 10th. New rules dictate that a team that is not part of MLB revenue-sharing cannot pick in the lottery in back-to-back years, and the Sox picked fifth in 2024, using the selection on Arkansas pitcher Hagen Smith. Simply put, loading up on top-five picks to build up a farm system — as the Orioles, Astros and Cubs did in recent memory — is a thing of the past.

“There's different ways to kind of go through these transitions or phases,” Getz said of what the rebuild blueprint looks like. “In the past, teams capitalized on getting high draft picks on a regular basis or trading certain players with a certain amount of service time left. You need to find these competitive advantages.

“Obviously, the rules have changed. But that doesn't mean that you don't focus on the draft anymore because you still have to do that.”

The limited budget has handicapped the entire franchise

The lack of talent throughout the White Sox organization is a microcosm of a much larger issue for the team as they try to turn their misfortune around. Over the past decade, the White Sox have operated more like a mom-and-pop shop than a modern MLB franchise.

They’ve been in the top 10 in team payroll just once in the past 10 years, whereas the team that won the World Series was in the top 10 in eight of those seasons. Handcuffed in part by limited resources, the player development in the big leagues and the minors has left a lot to be desired in Chicago, as has the team’s ability to hit on picks in the draft. Since 2000, just three of Chicago’s first-rounders have made multiple All-Star appearances: Anderson, Rodón and Chris Sale.

Underachieving players, poor player development and scouting misses have all been part of the demise of the White Sox over the past three seasons, but the throughline is the lack of investment. For that, plenty of blame falls at the feet of the team’s majority owner and chairman, Jerry Reinsdorf.

Worst of all, at the point when the previous rebuild entered its competitive window, as opposed to investing in one of the sport's brightest young teams, the front office cut corners and settled in free agency. When players such as Bryce Harper, Corey Seager, Marcus Semien, Manny Machado or Trevor Story were available, the Sox ended up with the likes of Leury García, Josh Harrison and Dallas Keuchel, who were all eventually designated for assignment and released.

The White Sox remain one of only two teams in MLB that have never signed a $100 million free-agent contract. (The Oakland A's are the other.)

Where do the White Sox go from here?

Getz, who was promoted from assistant general manager after the firing of former GM Hahn and executive vice president Kenny Williams last summer, is now tasked with overseeing another White Sox rebuild, one that is off to a rocky start.

Regardless of outcomes, for the White Sox, this year will be about taking stock in terms of talent both at the big-league level and in the minor leagues. Which players are making progress developmentally? Which players aren’t? Who’s in Chicago to stay? Who isn’t? The answers to those questions will ultimately determine how the team’s next core takes shape.

“It's going to take time,” Getz said. “But you've got to zoom out and really keep everyone focused on what we're trying to accomplish as we work through this and still aim for something that's certainly bigger than what's in front of us right now.

“There's development going on at the minor-league level. There's development at the major-league level. There's decisions that are going to need to be made. We're just going to continue to do that and not lose sight of what we're working toward.”

In years past, one of the biggest knocks on the White Sox has been a lack of influence from voices outside the organization, especially after the internal promotion of Getz last season. But heading into this year, the Sox GM brought in several new executives — including assistant GM Josh Barfield from Arizona, director of pitching Brian Bannister from San Francisco and personnel director Gene Watson from Kansas City — to provide a fresh perspective on how things are done.

Still, the reality is that things were likely going to get worse before they get better, which was evident on Monday night in Oakland.

The White Sox haven’t gotten to the point where they can identify their next core, and even with top prospect Colson Montgomery knocking on the door of the big leagues, it’ll take much more than their 2021 first-round draft pick to get this organization back on track.

This year, success for the White Sox will be measured not by their record but by their development as they head in a new direction. But that won’t make things any easier for the players on the field as the team restarts on the road to baseball relevance.

As second baseman Nicky Lopez said: “No one likes losing. No one wants to struggle. You can use the term, ‘it’s early,’ but it’s our livelihoods, it’s our careers, and no one likes to struggle.”