After back-to-back-to-back 100+ loss campaigns, it's obvious what the Chicago White Sox need this offseason: everything.
On a positive note, a number of key contributors emerged in 2025, like top prospects Kyle Teel and Colson Montgomery. Thanks to the front office's purging over the past two seasons, the payroll is also squeaky clean, save for the $30+ million owed to Andrew Benintendi through 2027 and whatever is going on with Luis Robert Jr.
After slashing payroll from $150 million in 2024 to $85 million in 2025, it's evident that the White Sox have money to spend this winter, especially if they can offload one or both of their expensive outfielders.
While they're too far away from contention to swim in the deep end of the free-agent waters -- not to mention the unknown ramifications of the impending 2027 lockout -- they still can and should add a few veterans with winning mentalities in order to change the vibes around the clubhouse.
There's plenty of soon-to-be available players that fit that mold, though perhaps none are more attractive than certified White Sox killer Josh Naylor.
White Sox should pay up for Josh Naylor in free agency this offseason
White Sox fans are all too familiar with Naylor's exploits during his time with the Guardians, but 2025 has arguably been his best effort yet.
Between the Arizona Diamondbacks and Seattle Mariners, the first baseman is hitting .295/.353/.462 with a 128 wRC+. He also hit at least 20 home runs for the third time in the past four seasons.
Considering that White Sox first basemen ranked 27th in baseball this past season with an 83 wRC+, it's no surprise that fans are clamoring for Naylor to join the fray this winter.
If Josh Naylor signs with the White Sox I will (probably not) forgive all his sins of crushing us mercilessly as a Guardian
— Spooky Brett (@haffball7) October 11, 2025
They know the reality. They understand the parameters.
Some of them do not care. Bring him here.
I know it's impractical but I'd love the White Sox to go after Josh Naylor this free agency.
— Josh Nelson - Sox Machine (@soxmachine_josh) October 13, 2025
Recent contract projections peg Naylor, 28, as a likely candidate to receive somewhere in the vicinity of $20 million per year, which would mean a nine-figure contract over a five-year period. That's more than doable for the White Sox -- especially since Naylor isn't eligible for the qualifying offer after being traded midseason -- though it does crush Benintendi's total contract value ($75 million) that currently leads the team.
Sometimes, bad teams need to pay up for good players, and that's simply going to be the case with a guy like Naylor coming off a career-best season.
If nothing else, signing Naylor would keep his bat from torching this team over and over again. In 55 career games against the Pale Hose, the left-handed slugger is batting .353/.395/.617, good for an OPS of 1.012. For good measure, he's also hit 31 extra-base hits (20 doubles, 11 home runs) and driven in 42 RBI in those contests.
For those wondering, his batting line increases to .366/.393/.661 (1.054 OPS) when playing in Rate Field. Sounds like the kind of guy you want on your roster, no?