PREAMBLE
I remember when I first developed skepticism about Santa Claus. The story was compelling, no doubt, but something just didn’t add up. Still, I wanted to believe, so I did. Then, one day, a Sunday School teacher, of all people, spilled the beans. “Oh, y’all don’t still believe in that stuff, do you?” Well… not anymore! That confirmed it.
I remember developing skepticism about rebuilds during the early Hahn years. But that administration played the role of my Sunday School teacher: they crushed my credulity.
So, I no longer believe in “rebuilds.” Of course there are times when a team should prioritize the future or draw the payroll back for a year or two. But a tear-it-down, five-plus-year “rebuild”? That’s a front office ploy to avoid spending money. The idea that a team must intentionally suck for five years to get good again is nonsense.
Even if we buy into Jerry’s rebuild fantasy, we should ask: when is the time to pivot toward trying again? I would say when two things are happening: (1) the prospects acquired in the previous teardown are arriving and (2) the payroll is reset. The White Sox check both of these boxes.
All this leads me to one conclusion: it’s time to try to win again. I think Jim’s $90m budget is a reasonable, realistic guess. But I’ll squeeze a little more out of Jerry. I’ll point to increased fan interest in this young core and argue that two big, name-brand All Star additions will put more butts in seats. I’ll also make the case that pouring a bunch of money into one year additions is a waste: let’s invest in guys who could be around a few years. Let’s invest in this team. So I’ll press him for only $7m more — for a budget of $97m. That would’ve been good for 26th in baseball for OD 2025.
I’m under no illusion that this team will be a World Series favorite in 2026. But “trying” should be the minimum bar every team jumps over. Of course I’m not mortgaging the future to win now—I’m not moving Billy Carlson or Caleb Bonemer to get better in 2026. But I do want this team to win now. I think the team I built should win 75-85 games and be relevant in August and September. Hopefully, it’s only the first step. This is still a year of development, and the hope is that this year provides proof of concept for a larger push — financially, but also with matriculating prospects — in 2027.
COACHING STAFF
- Hitting coach: [Left blank]
- Pitching coach: [Left blank]
I don't know the terrain of assistant coaches well enough to make any good suggestions. In general, I would lean on Bannister and Fuller to help make a decision and would want a coach that fits their style.
ARBITRATION-ELIGIBLE PLAYERS
- Mike Tauchman: Tender
- Steven Wilson: Non-tender
- Derek Hill: Non-tender
The Sox are going to need some OF and I like keeping Tauchman around as a veteran leader + lefty bat (and, as we'll see, he'll be my only one in the OF). I'll be okay if they pick up Wilson's option but I have different ideas for that money.
CLUB OPTIONS
- Luis Robert Jr.: Exercise $10 million contract
- Martín Perez: Buy out for $1.5 million
I think Robert would easily surpass this if he were a free agent (Spotrac has 6 years, $131m as his market value). I think it's the easiest decision among the tenders/options. Perez is an easy buyout.
FREE AGENTS
It’s difficult to peg values for players like this, so I’m using Spotrac’s Market Value as the base. But I also add a “White Sox Tax” — the extra price you pay for being bad and having a poor reputation among players.
(1) Sign Dylan Cease — 6 years, $170m ($28m AAV)
I didn’t want to sign Cease because that felt like the boring option. But anything else felt like getting too cute. We know Cease's pros and cons, but he’s simply one of the most durable pitchers out there. He has his ups and downs, but he’s exactly the stability this rotation needs and, because of those downs, is just in the range of “affordable.”
(2) Sign Luis Arraez — 5 years, $75m ($15m AAV)
He was on track for a huge contract this offseason, but his hitting took a step back in 2025 and he’s at 1B now. Spotrac has his market value at 5 years, $70m. I’m signing him to play 1B and 2B, since he can still play there. That gives Venable a little flexibility and he can rotate guys around to find the right mix for 2026. While Arraez isn’t exactly a thrilling option, I think he’ll age well and he comes at a reasonable price. Plus, he’s only entering his age 29 season—so I think there’s plenty left to give.
(3) Sign Jarred Kelenic — 3 years, $15m ($5m AAV; PO after year 2)
I have no idea on this contract since Spotrac didn’t give his market value. On the one hand, he’s a veteran-ish guy coming off a miserable season and a lackluster one before that. That usually spells a minor league deal. On the other hand, he’s hitting the market at 26-years-old and he’s less than a full season’s worth of PA away from a solid year (110 wRC+). At this price, I like this for the White Sox—it gets them some OF depth but with a little upside. It’s too easy to see this flushing $15m for a 4th OF, so I grant some risk here. But that’s a risk they can afford.
(4) Sign Erick Fedde — 1 year, $800k
Let Fedde stand in for generic SP depth. I don’t really care who this is and I tell Bannister/the new Sox pitching coach to pick whomever they want under $2m.
(5) Sign Manuel Margot — 1 year, $1m
Same as with Fedde but with OF depth.
TRADES
I’m throwing some stuff on the wall here to see what sticks. I consider these more “trade vibes” than very specific ideas: in other words, they capture the kind of trade I think the Sox should explore. If you don’t think this particular trade works, there’s probably another version of it somewhere that does.
(1) Trade Edgar Quero + Grant Taylor to the Dodgers for Andy Pages
A lot of young talent in this trade and, frankly, I don’t know what to make of it. It’s a lot to give up on both sides. But here’s how I think about it:
Why the Dodgers make this trade: Pages is a lot to give up, but it’s not yet clear how much. He was excellent this year (4.0 fWAR, 113 wRC+) but doesn’t look like a superstar, either. In moving him, they get two exceptional talents in return, each with more team control. The Dodgers have had the hardest time finding a stable catching presence alongside Will Smith. Smith is an excellent catcher, but he’ll turn 31 this offseason and only started 98 games. I suspect the Dodgers would love to have a guy they can trust to catch alongside Smith. But I think in their minds the real prize is Taylor and I think they try to make him a starter. Obviously I don’t know what they think about him, but it feels like a very Dodgers move to turn Taylor into basically Tyler Glasnow.
Why the White Sox make this trade: Quero and Taylor are a lot to give up, but with Teel in the fold Quero is a luxury and the Sox view Taylor as a reliever. They should therefore capitalize on the value of both assets and they do in a major way by acquiring OF help. Pages brings huge power to the lineup that would really play on the South Side, and he’s an OF stalwart through the (fingers crossed) next good White Sox “contention window.” He’s Plan A for CF in the post-Robert era.
(2) Trade Andrew Benintendi + $12m ($6m/year) to the Kansas City Royals for Daniel Lynch
The Royals were dead last in LF production last year and they had a good experience with Benintendi in his short stay there previously. If the Sox are willing to eat some money, I think this is the kind of move the Royals are interested in. Lynch is hitting arbitration, too, so the Royals should be willing to move on from him. The White Sox could use some bullpen stability, and he might be their best candidate to close.
(3) Trade Lenyn Sosa to the Angels for Reid Detmers
The Lenynites can save their dissent: I know the arguments for him but I still think he’s the odd man out in this infield. I would rather see a revamped Curtis Mead and Chase Meidroth get some run. Detmers is a kind of project himself. After several years of struggling as a starter, the Angels moved him to the bullpen. I think the Sox should explore moving him back to starter, but for the purposes of this exercise I’ll assume he stays in the bullpen.
(4) Trade Yoendrys Gomez to the Orioles for Kade Strowd
FG ranked Strowd (40 FV) 33rd in the O’s system, but he’s a 28 year old reliever with uneven results in the high minors and in his SSS in MLB. But he’s got some big strikeout stuff and the Sox need to add to the bullpen. Gomez fills out some starting pitching depth for the O’s.
SUMMARY
26-Man Roster
C - Kyle Teel
1B - Luis Arraez
2B - Chase Meidroth
SS - Colson Montgomery
3B - Miguel Vargas
LF - Jarred Kelenic
CF - Luis Robert
RF - Andy Pages
DH - Mike Tauchman
Bench: Korey Lee (C), Curtis Mead (2B/3B), Brooks Baldwin (Utl), Manuel Margot (OF)
SP1 - Dylan Cease
SP2 - Shane Smith
SP3 - Davis Martin
SP4 - Sean Burke
SP5 - Erick Fedde
(Hagan Smith — I’m listing him here because I think he’s up sooner rather than later. He might even be on my OD roster, since I assume someone gets hurt)
Bullpen - Daniel Lynch IV, Reid Detmers, Jordan Leasure, Mike Vasil, Kade Strowd, Tyler Gilbert, Wikelman Gonzalez, Fraser Ellard
THE MONEY (Name - 2026 Payroll Obligation)
Dylan Cease - $28m
Luis Robert - $20m
Luis Arraez - $15m
Beni Dead Money - $6m
Jarred Kelenic - $5m
Mike Tauchman - $3.5m
Reid Detmers - $2.75m
Manuel Margot - $1m
Daniel Lynch - $1m
Erick Fedde - $800k
17 players x $770k - ~$14m
Abreu & Hendriks; Perez Buyout - $0.0m (Ishbias paying down debt)
TOTAL = ~$97m
Okay, so I cheated a bit on the payroll. But however you slice it, this team is still *bottom five in baseball in payroll.* This is not a wild spending spree. It’s a reasonable step forward. This team is not a World Series contender in 2026, but the thought is that they are ready to strike next offseason. After another year of developing this core, getting more of those big money contracts off the books, and matriculating Smith, Montgomery, and Schultz to Chicago, they should be in good shape next offseason. If we go this route, 2027 looks a lot brighter, with fewer holes to fill, more talent, and other prospects (Carlson, Bonemer) possibly in the high minors. This is the quick turnaround Jerry asked for.
