Last season, the AL Central was decided in a September sprint to the finish, as the Cleveland Guardians made one of the most stunning late rallies in MLB history, overcoming an 11-game deficit in early September to win the division.
For the Chicago White Sox, this must feel like déjà vu. Last season, Chicago lost 100 games, but it has led the Central for most of the season. However, a 3-7 mark in the last 10 games has left the White Sox with just a two-game cushion, and they still have a three-game series in Cleveland remaining.
Thus, winning tonight’s 7:40 p.m. ET series finale against the Pittsburgh Pirates, avoiding a sweep and putting an additional half-game cushion in between themselves and the Guardians, is paramount. For that task, the White Sox will turn to Hagen Smith as an opener ahead of Erick Fedde, while Jared Jones will start for Pittsburgh.
Let’s break down this must-win showdown with some odds and lines at DraftKings Sportsbook.
Pittsburgh Pirates at Chicago White Sox Best Bets
- Chicago White Sox Moneyline (-110): I’m actually a fan of Chicago’s pitching plan; Smith should be able to produce at least two clean innings, and Fedde has been in solid form, especially at home. Jones is decent, but I don’t trust this Pirates offense.
- Munetaka Murakami 1+ RBI’s (+176): Murakami has started to find his swing again after a dastardly stretch, and he’s gone deep twice in his last four games. Nearly half of Jones’ pitches to lefties are four-seamers, and Murakami has a .569 xSLG against righty four-seamers.
Pittsburgh Pirates at Chicago White Sox prediction, preview
At 73-73, the Pirates would be just a half-game behind Cleveland for the final Wild Card spot if they played in the AL, but since they ply their trade on the Senior Circuit, they trail the final Wild Card place by five games. Still, given that Pittsburgh finished 71-91 last season, this season represents significant progress, and a win tonight would vault the Pirates over .500 for the first time since July 30. Pittsburgh has fallen off offensively in the last month, posting the fifth-worst OPS in the last 30 days, although rookie Konnor Griffin (who just returned after missing two months with a finger injury) should help, especially if Oneil Cruz (.866 OPS since returning from his own injury on August 18) stays hot. The Pirates have primarily been winning through their pitching; their bullpen has put up a 3.26 ERA since the All-Star break, and their rotation has a 3.25 mark so far in September. It’s been a miserable season for 2025 Cy Young Award winner Paul Skenes, but he’s settled down with two solid starts in his last three, and trade deadline acquisitions Camilo Doval and Lake Bachar have proven solid. Mason Montgomery also hasn’t given up a run since July 20, though his rough start to the season means his ERA still stands at just 2.82.
Chicago still seems fairly likely to hold on to its division lead in the end, given that it has the third-easiest remaining schedule in baseball and the Guardians merely the eighth-easiest, but with just a 3-7 record in its last 10 games, it’s gotten cold at the wrong time. The White Sox’s offense has continued to rake; over the last 30 days, they rank ninth in OPS, as despite Munetaka Murakami (a .617 OPS since the start of August) continuing to slump, Triston Peters (1.023 in that same span), Miguel Vargas, and utilityman Randal Grichuk have picked up the slack. However, Chicago’s pitching has been horrible, as its rotation had an eye-popping 6.21 ERA in August and has only improved to 5.23 so far in September. Luis Castillo, acquired from the Seattle Mariners at the trade deadline, has arguably been the worst of the bunch. At least the White Sox’s bullpen has been elite, pitching to a 3.22 ERA after the All-Star break, but if Chicago crashes out of the division lead, its lackluster starters will be a primary reason why.
Jones has mostly had a decent season. He pitched to a 4.14 ERA as a rookie in 2024 before missing the entire 2025 season while recovering from internal brace surgery, and since returning in May 2026, he’s recorded a 4.46 ERA in 17 starts. In fact, since a blow-up on June 15 lifted his ERA to 6.23, he’s had a sub-4 mark in his last 13 starts, allowing three or fewer earned runs in all but one of those appearances. Advanced numbers suggest that Pittsburgh should have a good chance with him on the mound, as he ranks in the 69th percentile in xERA and the 76th in xBA. The flamethrower has deceived batters particularly well, with top-quintile whiff and strikeout rates, and any team that rosters both Murakami and Colson Montgomery is going to whiff a ton. He’s paired that with decent control, which should be an asset against a White Sox team that walks a lot. His primary issue is his tendency to give up hard hits, as he ranks in the 41st percentile or lower in hard-hit rate, barrel rate, and average exit velocity, and as the only team in the league with three 30-homer batters, Chicago is well-suited to take advantage of that. He’s been slightly better on the road, but the White Sox have a 49-point home-road discrepancy in OPS.
Smith has previously only worked out of the bullpen in MLB, though he’s at least pitched into a second inning of work in eight of his 10 appearances, including three scoreless innings against the Minnesota Twins on Sunday. Given that he’s recorded a 0.56 ERA in his first 10 MLB outings and a 2.10 FIP and that he has previous experience as a starter in the minors, he should be able to keep the scoreline clean for two or three innings before turning it over to a long reliever (likely Fedde). It’s a pitching plan that could work well for Chicago; Fedde has pitched to a 3.00 ERA since the start of June. Smith would have a top-decile xBA, whiff rate, strikeout rate, and barrel rate if he’d pitched enough innings to qualify, and while advanced analytics don’t like Fedde as much (he has a 26th-percentile xERA and rarely induces chases or strikeouts, Pittsburgh’s biggest weaknesses), at least he’s exhibited solid control. The Pirates rank slightly above the league average in each of the slugging categories, and with a 54th-percentile average exit velocity, Fedde should be able to keep them in check. He has an impressive 3.11 ERA at home this season, and Pittsburgh has had baseball’s 10th-worst road offense this season.
Pittsburgh Pirates at Chicago White Sox pick, best bet
Best Bet: Chicago White Sox Moneyline (-110)
The odds suggest that this game is a pure toss-up, but despite his decent form, the Pirates have lost in nine of Jones’ last 13 starts. Plus, Pittsburgh has generally been worse on the road, especially offensively. Chicago has the AL’s second-best home record.
Strong Lean: Munetaka Murakami 1+ RBI’s (+176)
It’s a small sample size, but Murakami has driven in at least one run in three of his past four games. Will Venable has dropped him to hit right behind Vargas, the AL leader in runs.
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