The Chicago White Sox held a commanding lead in the AL Central for much of this season, but the Southsiders have now lost seven of their last ten following Sunday's stinker in St. Louis. On the other hand, the Cleveland Guardians have caught fire at the right time, parlaying a productive trade deadline into on-field results. The White Sox (76-73) are now a mere half-game ahead of Cleveland (76-74) in the division, with momentum working against them.
Chicago still has a clear path to the postseason, but the Sox could end up as the No. 6 seed instead of the No. 2 seed, which greatly impacts their ability to press deep into October. While there's time left to salvage things, we can start assigning blame to these White Sox.
DH Andrew Benintendi
Andrew Benintendi is one of the few real veterans in the White Sox lineup. He has enjoyed a solid season, with a .722 OPS and 100 wRC+, but it's hard to express full faith in the 32-year-old DH. He's showing exactly why of late, slumping to a .511 OPS since the calendar flipped to September.
Benintendi has never really lacked for power — he has three 20-homer campaigns under his belt — but he takes an aggressive approach, which can sometimes get the best of him. Beyond strikeouts, Benintendi has to worry about torpedoing at-bats with soft contact on bad pitches.
He's stuck in a platoon with Randal Grichuk, who's holding up his end of the bargain against left-handed pitching. Benintendi's White Sox tenure has been rife with criticism and disappointment, and he deserves credit for his perseverence. But if he continues on this cold spell, Chicagoans won't have many words of encouragement.
OF Brenton Doyle
All too predictably, Brenton Doyle arrived in Chicago at the deadline and basically kept doing exactly what he was doing in Colorado. A two-time Gold Glove winner once propped up as a cornerstone of the Rockies' future, Doyle has never quite figured it out at the plate. Unfortunately, the 28-year-old is trending in the wrong direction. He has a .565 OPS and 48 wRC+ on the season, with a -0.9 fWAR — the worst on the team.
Doyle's numbers since the deadline move are similarly poor, with a .554 OPS in 29 appearances for the Southsiders. Chicago acquired Doyle with an additional three years of club control, so it's a long-term arrangement. At his current pace, however, it's fair to wonder how much longer the White Sox will be able to justify keeping Doyle on the MLB roster.
In addition to his nonexistent production at the plate, Doyle's defense has dramatically regressed this season. He still has a monster arm and he's a show-stopping athlete, but he's not making the reads he once did. He was, perhaps unforgivably, the "best" bat Chicago added at the deadline. Call it a bad investment.
RHP Luis Castillo
Another deadline acquisition that was bound to age poorly, the White Sox acquired Luis Castillo from the Mariners in exchange for reliever Seranthony Domínguez and light prospect capital. It was basically a salary dump for Seattle and a buy-low gamble for the Sox, hoping a three-time All-Star could find new life in a more competitive environment.
Castillo isn't ancient — he's 33 years old — but it sure feels like the right-hander is over the hill, to be blunt. He has a 5.67 ERA on the season and a 7.76 ERA in seven appearances (six starts) since the move to Chicago. The White Sox are already pitching him behind an opener. Chicago's rotation is easily its biggest weakness. There was a hope that Castillo could be sharp enough to start in October. Now, it's fair to wonder if the White Sox should let Castillo anywhere near the mound in the postseason, assuming they can even get there.
The veteran is still under contract through 2027, so Chicago can hope for an offseason reinvention. In the meantime, Castillo's collapse has left the White Sox scrambling for an answer to their rotation woes that does not, at present, exist.
SS Colson Montgomery
On the surface, second-year shortstop Colson Montgomery is enjoying a brilliant campaign for the White Sox. He's up to 31 home runs and 84 RBI, with elite defensive metrics (12 outs above average!) at a premium position. And there's still every reason to believe the 24-year-old can become a cornerstone for the young, ascendant White Sox.
That said, Montgomery is spiraling at the plate right now. He's been slumping for a couple months at this point, but it's not getting better. He has a .594 OPS in September with four times as many strikeouts (20) as hits (five) in that 11-game span.
This has always been the issue for Montgomery, whose elite bat speed and natural power is too often undermined because he just can't generate consistent contact, either in or out of the strike zone. His 34.7 percent strikeout rate this season sits in MLB's bottom percentile. The White Sox need Montgomery to dial in and take a more disciplined approach, lest he swing them out of the division lead (or, god forbid, the playoffs).
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