The Chicago White Sox are bound headlong for the first division title since 2008, and they're still in the mix for top overall seed in the American League. In related matters, the SportsLine Projection System also gives the White Sox a 99.8 percent chance of making the postseason, which is the highest current figure of any AL team. Those are laudable results, but the greater goal -- the goal that will inform any appraisal of the White Sox's 2021 season -- is a deep playoff run. On that front, there's some cause for concern. 

The White Sox made the expanded postseason in the abbreviated 2020 season, but they were bounced in the opening round by the A's, who are not typically in the position of bouncing anyone in the opening round. Then-manager Rick Renteria had guided the Sox to their first winning season since 2012 and their first postseason berth since that aforementioned campaign of 2008. Still and yet, Renteria was let go and replaced by long-retired Hall of Famer Tony La Russa. The implicit mandate is that La Russa, in his second stint as White Sox manager, would not only get the club back the postseason but get them much closer to the belt and title than Renteria did. It's worth noting that right now La Russa's White Sox have a lower win percentage than they did last season under Renteria, but, again, the postseason will be the referendum on one of the strangest job decisions in recent memory. 

Now back to the "cause for concern" noted above. Simply put, the White Sox have played a thoroughly weak schedule in 2021 and have largely flopped against quality competition. Since competition in the postseason is necessarily of the quality variety, this could be a fatal shortcoming. 

On the first point -- the part about the weak schedule -- this is largely a function of playing almost half your games against the largely miserable remainder of the AL Central. Teams in the AL Central other than the White Sox -- i.e., Cleveland, the Tigers, the Twins, and the Royals -- all have losing records and all have been out-scored by the opposition by a wide margin. Combined, those four teams are 38 games below .500 and have a run differential of minus-270. As for the White Sox, they've now played 81 games against teams with losing records, or more than two-thirds of their entire schedule. Those 81 games against losing teams make for the highest such figure in all of baseball by a huge margin. As well, the White Sox per Power Rankings Guru rank last in all of MLB in strength of schedule. That's what happens when you're the only good team in a division and you don't have to play yourself. 

All of this could be dismissed easily enough had the White Sox proved themselves against worthier opponents, but they haven't done that. On Sunday, they dropped the rubber match of their series against the Yankees and their highly diminished roster. Add those games into the mix, and the White Sox are now 16-21 against teams with winning records in 2021. Among the seven teams presently in playoff contention in the AL -- i.e., the White Sox, Rays, Astros, Red Sox, Yankees, Blue Jays, and A's -- only one team, Oakland, has a lower win percentage against above .500 teams than the White Sox do. (If you wish to include the Mariners as a contender, then know that they, too, have been better against winning teams than the White Sox.) 

And if the current playoff positions hold? That would mean the AL playoff field would be the White Sox, Rays, Astros, A's, and Red Sox. This season, the White Sox against those four of those five other teams are a combined 7-12, and in those 19 games the White Sox have posted a run differential of minus-26. (On Monday, the White Sox meet the A's for the first time in 2021, as a four-game set in Chicago begins.)

None of this is to say the White Sox are necessarily doomed this October. Above all, randomness rules when it comes to playoff baseball, and predicting who's going to emerge from the 10-team fray is typically folly. If you're in the postseason, you necessarily have a reasonable chance to win it all, and let it be said that the White Sox are genuinely a very good team. Over the last decade, however, only one team -- the 2014 Giants -- has won the World Series despite having a losing record against above-.500 teams during the regular season. The prevailing reality is that the White Sox in 2021 have fattened up on lesser competition, which is what they're supposed to do, but won at just a .432 clip against the kinds of teams they're likely to face in the postseason. 

The Sox's roster is stronger now that it has been all season, what with the semi-recent returns of Eloy Jimenez and Luis Robert and the deadline additions of Craig Kimbrel, Cesar Hernandez, and Ryan Tepera. While that assemblage very nearly got swept by a Yankees team wracked by COVID and injury, the Sox are about to play 11 straight against the A's, Rays, and Blue Jays. Those, of course, are all teams they could plausibly face in the playoffs, and this presents the Sox with a chance to flip the script of note. 

To repeat, the White Sox because of their recent trajectory and most especially because of the managerial change have a great deal riding on the playoffs. Thus far, though, they've struggled against the very sort of team that's likely to stand between them and realization of those goals in which they're so heavily invested.