The Ideal White Sox Offseason — Within Reason

We’re only a few weeks away from the MLB Winter Meetings, and the stove is finally starting to warm up.

A few preliminary signings and minor trades have come across the wire, but most teams — including the Chicago White Sox — have stayed dormant since free agency opened. Chicago is still assessing the market, scouting international talent, talking to agents, and shaping its offseason blueprint.

Ah yes…the offseason plan. The thing every fan builds in their head every winter, only to watch it fall apart piece by piece. That’s especially true for White Sox fans, who are regularly let down by frugal ownership and half-measures.

Nonetheless, here’s my attempt to put together a realistic blueprint. Would Kyle Tucker look awesome in a White Sox uniform playing right field next season? Absolutely. But let’s try to keep things in the realm of reality. 

I put together a series of free agent signings and trades the White Sox could make over the next few months that I believe would be:

• Ideal for the club in 2026 and beyond
• Realistic targets given Chicago’s needs and financial limitations

The current projected White Sox payroll for 2026 is just under $60 million (factoring in arbitration and pre-arb estimates). I'll be keeping that number under $100 million — a threshold only five teams dipped below last season — while still putting together a competitive product fans would actually pay to watch.

Using Spotrac and ESPN contract projections, here’s how I’d use roughly $40 million to build a better, deeper, more entertaining 2026 White Sox team.

FREE AGENT ADDITIONS

Ryan O’Hearn — 1B/OF

Contract: Two years, $27 million

The Sox have already been linked to Ryan O’Hearn, and the fit makes too much sense to ignore. He’s a left-handed bat with a healthy dose of pop, reliable production, and defensive versatility.

He fills the hole at first base, but being able to play a corner outfield spot also gives Will Venable flexibility to move pieces around — especially Andrew Benintendi and Mike Tauchman. O’Hearn already has ties to director of hitting Ryan Fuller from his Baltimore breakout, and his .445 slugging percentage over the last three seasons would slot nicely into the heart of a young lineup.

A real need, a real fit, and one that has a real chance of actually happening.

Emilio Pagán — RHP

Contract: Two years, $22 million

My best guess at predicting which closer the White Sox have interest in would be as good as throwing a blind dart at the free-agent reliever board. The bullpen is a top priority — and recent comments on Grant Taylor make it clear Chicago wants a proven closer in 2026.

There's plenty of options available and a handful of arms that should get similar contracts on the open market.

Pagán’s advanced metrics jump out to me. He's elite in expected batting average and expected ERA. A 0.91 WHIP and 10.6 K/9 is everything you could want out of a ninth inning guy. It’s no surprise multiple teams are already circling for his services.

If it’s Pagán — great. If it’s another proven late-inning arm on a similar contract — also great. The Sox just need one of them.

Rob Refsnyder — OF

Contract: One year, $5 million

The Sox need a corner outfielder, and while O’Hearn helps, they still need someone who can platoon with Mike Tauchman and keep his soon-to-be 35-year-old body from breaking down again.

Enter Rob Refsnyder.

Against lefties in 2025, he hit .302 with a .959 OPS. In 2024? .302 with a .941 OPS. In 2023? .308 with an .828 OPS.

That is high-end, consistent production against southpaws. Add in his defensive versatility and ability to play all three outfield spots (and even some infield in an emergency), and he’s the perfect complementary piece for the White Sox. 

An affordable, short-term contract that immediately improves the MLB depth.

John Means — LHP

Contract: One year, $2 million + club option for 2027

John Means has a 3.60 ERA since the start 2019 and was once an All-Star in Baltimore. But multiple injuries — including multiple Tommy John surgeries — have derailed what could’ve been a strong prime.

Means signed a one-year deal with the Cleveland Guardians in 2025 with a club option for the 2026 season, but only recovered from TJ enough to make some rehab starts down the stretch of the season. He had a 6.08 ERA in the minor leagues, which didn’t inspire much confidence and eventually pushed Cleveland to decline his club option for 2026, making him a free agent. But as things stand right now, Means should be healthy to pitch at the start of 2026. 

This is the exact kind of lottery ticket the White Sox should take.

If he wins a rotation spot — great. If he transitions to the bullpen — great. If he provides left-handed depth in Triple-A — still fine.

Low risk. Decent upside. Either way, I like the potential here and the White Sox wouldn’t be attached to the financials enough to keep him around if he's not producing.

José Quintana — LHP

Contract: One year, $5 million

The White Sox need at least one veteran to insert into the starting rotation for 2026, and they need at least one left-hander in case things don’t work out with Means in my imaginary world. A reunion with José Quintana checks both boxes.

Yes, he’s 37. Yes, the stuff isn’t what it once was. But Quintana still went 11–7 with a 3.96 ERA for Milwaukee last season and gave them exactly what they needed when injuries piled up.

Quintana is reliable, usually durable, and knows how to pitch through traffic. Even better, he showed bullpen versatility with the Brewers in October.

It would be both a nostalgic and practical reunion for Quintana on the South Side and a great way to close out a career that’s now pushing 15 MLB seasons.

THE TRADE

White Sox trade INF Lenyn Sosa, LHP Tyler Schweitzer to San Francisco Giants for RHP Hayden Birdsong

I firmly believe the Sox should move Lenyn Sosa this offseason — not because he’s a bad player, but because he’s a bad fit for their roster construction. But it’s hard to know exactly what his market looks like.

What I do know is that the White Sox have an infield surplus. I also know that Sosa doesn’t have a defensive home, and while his bat plays at second base (22 home runs and 75 RBIs in 2025), it's not good enough to hold down the fort as a regular first baseman or DH. The on-base problems limit his ceiling, with a .293 OBP in 2025 being Sosa's career best.

San Francisco, meanwhile, desperately needs right-handed power and ranked dead-last in OPS vs. lefties last season (.631). Their second-base options are underwhelming. Casey Schmitt — a natural third baseman — hit just .196 with two home runs against lefties last year. Christian Koss, a 2025 rookie, posted a .642 OPS against southpaws.

Sosa would get meaningful at-bats to help a lineup that was in the bottom half of the league in home runs despite significant financial investments to their offense. 

The Giants also have rotation depth. Logan Webb, Robbie Ray, Landon Roupp, and Carson Whisenhunt, plus an inevitable splash signing in free agency. That makes former Brian Bannister pupil Hayden Birdsong expendable.

Birdsong — an Illinois native — has plus fastball/curveball offerings, a great frame, and a pitch (the kick change) that Chicago has already weaponized with Davis Martin. He’s inconsistent, mostly because of his control since being called up, but the upside is there and he's only 24 year old.

As for Schweitzer, he’s likely to be squeezed off the 40-man at some point this winter, so including him sweetens the pot while the White Sox clear the way for other young pitchers in the organization.

This trade makes sense for both sides — and gives the Sox another controllable young starter to build around.

OFFSEASON OVERVIEW

This entire plan adds roughly $35 million to the payroll, putting the Sox at about $95 million in 2026  — still bottom five in MLB.

Even for Jerry Reinsdorf, that’s doable.

And on the field, this offseason plan puts together a White Sox team that addresses their holes, has potential to be competitive, brings in upside for the rebuild, and maintains flexibility as the next wave of prospects debut

Here’s a look at a potential Opening Day 26-man roster for the White Sox following my offseason plan.. 

Projected Opening Day Roster (26-Man)

LINEUP:

C — Kyle Teel

1B — Ryan O’Hearn

2B — Chase Meidroth

3B — Miguel Vargas

SS — Colson Montgomery

LF — Andrew Benintendi

CF — Luis Robert Jr.

RF — Mike Tauchman / Rob Refsnyder

DH — Edgar Quero

BENCH: Brooks Baldwin, Derek Hill, Korey Lee or Curtis Mead

ROTATION: Shane Smith, Davis Martin, José Quintana, Sean Burke, Hayden Birdsong

*note - Shane Murphy, Ky Bush, Drew Thorpe, Mason Adams, John Means, and Jonathan Cannon all compete for the final spots.

BULLPEN: Grant Taylor, Mike Vasil, John Means, Brandon Eisert, Cam Booser, Steven Wilson, Jordan Leasure, Emilio Pagán (CL)

This is a team I can get excited about — a team that reasonably pushes past 70 wins and positions the Sox for contention in the years to follow.