On Friday, the Chicago White suffered their 90^th loss…in only 118 team games. That has got to be some kind of record, or at least high on a list of “all-time fastest to a milestone.” I haven’t dug that up yet, but three’s no need for a big number dive to know the Chicago White Sox are on a collision course with history. After Friday night’s “tough luck” loss to the cross-town rival Chicago Cubs, the not-so-Mighty Whiteys are sailing into waters seen only by a few major league teams this century…or the last one.

Headed into Saturday with 44 games left to play, the White Sox have compiled a record of 28 wins and 90 losses. That leaves the South Siders sitting on a winning percentage of only .237. Now, many other baseball writers out there are locked in on the White Sox and the possibility they can eclipse the modern-era record for losses currently held by the 1962 New York Mets.

But if they break that record by losing 121 games in 2024, does that make them a worse team then those expansion Mets? Does it make them the worst team ever? After all, not even the historically wretched St. Louis Browns weren’t the “Charlie Brown-iest” team for a single season. But there’s three reasons why we might be seeing the worst team baseball has fielded since 1900.

There’s plenty of numbers to tell the sad story of the 2024 Whiteys, but to truly grasp the futility of this team, one must look past the quantifiable. Let’s start with Friday night’s loss. It’s almost as if this team sets out every night to rip the guts out itself… along with those of it’s fans. Led by two Andrew Benintendi homers, the White Sox nearly dug themselves out of a 7-0 hole, only to some up short yet again. You simply can’t notch 100+ “Ls” in season without finding ways to lose.

A huge factor toward a monstrous amount of losing is to be a franchise which is completely directionless. 2024 is the first season under new general manager Chris Getz, who is discovering his lot in a White Sox life is a salvage operation. When all the other writers pen their dribbles on far the White Sox have sunk, universally they forget the 1962 Mets were as mentioned an expansion team featuring a roster of cast-offs, has-beens, and never-weres.

But the Mighty Whiteys were a play-off team in 2020, and won their division 2021. However, the most important constant on the south side of Chicago is White Sox owner Jerry Reinsdorf doing “Jerry Reinsdorf things.” A never-ending theme during the Reinsdorf administration is his steadfast (albeit contradictory) refusal to invest in the team in general…with the exception to overspend dramatically on a select class of free-agents. Never forget that Reinsdorf was the guy who filibustered during an owner’s meeting in the late 90s on the need to control rising salaries while simultaneously negotiating to make Albert Belle the highest-paid player in the game.

Stuff like that means it shouldn’t surprise anybody that a guy like Reinsdorf accompanies overspending with an inflated set of expectations. Specific to this case, Reinsdorf expected the Whiteys to win a World Series with the squad they fielded in 2020 and 2021. The problem is just a few years prior to that, the Whiteys were (again) a 100-loss team. Those playoff teams did have some Reinsdorf-acquired talent, but the ship sailed leaving the supporting cast on the docks. Because there wasn’t enough mortar to hold the new bricks together, manager Rick Renteria got the gate even though he was the mason who carried the hod for that 100-loss team; building it to play in October.

Once Reinsdorf’s team that really couldn’t run with the big dogs didn’t, the “Jerry Reinsdorf doing a Jerry Reinsdorf thing” happened. The Chicago White Sox became a two-year long “yard sale” dealing in talent by the pound…but while overpaying for certain free-agents like Andrew Benintendi.

Not only does that lay the foundation of “directionless,” the White Sox hardened it’s concrete by firing manager Pedro Grifol earlier this week. All Grifol did was take the helm in the wake of the Tony Biden LaRussa disaster and man the Whitey’s bridge as the Sox-tanic rammed the iceberg Jerry Reinsdorf put in it’s path.

Let’s recap. We’ve just established two factors putting the 2024 White Sox in the discussion for being one of the worst teams this game has ever seen.

1. Jerry Reinsdorf doing Jerry Reinsdorf things.
2. The Chicago White Sox are completely directionless.

#3 is all about a seriously scary number. We’ve already scratched the surface here, but there’s much more to the futility of the 2024 Chicago White Sox than just chasing the 1962 Mets’ loss record. The question was previously posed about the Whitey’s being worse than those expansion Mets. Frankly, I think the loss record is irrelevant. The aforementioned “scary number” does that.

I apologize in advance for the “Sabremetrics-y” feel to this, but measuring the depth of the White Sox’ descent can be done only by comparing the winning percentages of the worst of the worst indexed against the era in which they played.

The first graphic shows the teams with the twenty worst single-season winning percentages broken into three groups.

When the 2024 Chicago White Sox are added in place to this list, it’s clear they are amongst the worst of all time. But when one takes those teams and sorts them in ascending order of year, something very important to the “worst ever” argument becomes plainly visible.

Keeping the color-coding from the first graphic in mind, notice how the teams with similar losing percentages tend to cluster together. There’s likely plenty of reasons for that, but it is impossible to ignore the fact the 2024 Chicago White Sox have regressed to a level not seen in the major leagues in nearly 90 years.

In other words, the second graphic makes it clear there’s a correlation between eras in baseball and the winning percentage of the truly bad teams, and the trend was heading up…until now. Even if the White Sox don’t break the single-season records for losses, they’re still going to break a trend which dates back to the earliest days of the game.

To me, that feels worse.

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