The Chicago White Sox head to Progressive Field on Wednesday, September 16, 2026 for a 1:10 PM ET matinee against the Cleveland Guardians. Anthony Kay gets the start for Chicago against Cleveland's Parker Messick in what shapes up as a pitching matchup between two arms with something to prove down the stretch of the regular season. The game airs nationally on ESPN and the ESPN App, with radio coverage available locally on ESPN Chicago WMVP 1000 AM.
White Sox Starting Pitcher: Anthony Kay
Anthony Kay draws the assignment for Chicago on Wednesday. Kay has spent time in the big leagues previously and brings lefty experience to a Sox rotation that has leaned heavily on younger arms this season. Without a deep statistical ledger available for this outing, the focus will be on how Kay handles Cleveland's lineup — a group that has shown the ability to grind at-bats and put pressure on opposing pitchers. Kay's command and ability to work efficiently through the order will be the defining factor in how long he lasts and what kind of position he leaves the bullpen in.
Cleveland Starting Pitcher: Parker Messick
The Guardians counter with Parker Messick, a left-hander who has been part of Cleveland's pitching development pipeline. Messick is the kind of pitcher the Guardians have consistently turned to as they build organizational depth on the mound. For the White Sox offense, the key will be identifying his stuff early and not letting him settle into a comfortable rhythm against a lineup that needs to manufacture runs.
Keys to Watch for the White Sox
- Kay's command against a disciplined lineup: Cleveland does not chase. If Kay falls behind in counts, he will face a long afternoon. Getting ahead early is critical.
- Run support: The White Sox need to cash in when opportunities arise against a pitcher they may not have extensive scouting history on. Aggressive, smart baserunning matters in a day game road environment.
- Bullpen management: If Kay works into the fifth or sixth, the Sox coaching staff will need to navigate the middle innings carefully against a Cleveland lineup that can do damage late.
- Defensive execution: Progressive Field rewards clean defense. Errors or mental lapses on the road against a sharp opponent tend to compound quickly.
Prediction
This is a winnable game for Chicago, but it requires Kay to be sharp early and the offense to take advantage of opportunities against an unfamiliar arm in Messick. Cleveland is playing at home, which gives the Guardians a meaningful edge in a close contest. Expect a low-scoring game decided by three runs or fewer. The Sox have the pitching matchup to stay in this one — but whether they can get enough offensively on the road on a Wednesday afternoon is the real question. Edge: Guardians, 4–2.
