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The Chicago White Sox are quickly becoming the road warriors of the MLB playoffs.

After sweeping the Astros in Houston during the American League wild-card round, Chicago opened the ALDS by shutting out the Cleveland Guardians 3-0 on Saturday at Progressive Field.

Now the White Sox have a chance to seize control of the series.

A victory Monday would send them back home with a 2-0 lead and within one win of their first American League championship series appearance since their 2005 World Series-winning season.

The Guardians, meanwhile, are trying to avoid heading to Chicago facing elimination, with MLB strikeout leader Gavin Williams set to take the mound in a crucial Game 2.

Follow along for live updates, lineup news, key moments, analysis and highlights from White Sox vs. Guardians in the ALDS.

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The Wild Card Series came and went this year without much intrigue. The Yankees blew the Red Sox out of the water, the White Sox stuck the final stake into the dying heart of the Astros, and the Padres embarrassed the Cubs. None of those series were competitive, but there was one that at least reached a Game 3: the divisional battle between the Braves and Phillies.

For one side, it was a mental block that had to be erased. The Braves hadn’t won a playoff series since winning the World Series in 2021, and had lost to the Phillies in consecutive NLDS in 2022 and 2023 to springboard their latest contention window. It’s a win-now core, and even though they had a lot of issues, they weren’t a team that can accept a loss this early.

The other side couldn’t really accept that either: the Phillies had been eliminated earlier and earlier since a heartbreaking loss in the 2022 World Series. Their core was much older, with much less young talent to supplement it. They had stumbled into the playoffs with a disastrous final week that messed up their pitching. They had reached the point where most teams are at the end of their contention window. If you don’t show reason to believe in this core, it’s going to be dismantled.

The Braves won that grudge match in Game 3, sending the Phillies home with another disastrous season and ensuring no October baseball in the City of Brotherly Love for the first time in five years. It’s a sobering defeat for a team whose best players are past their prime, which has an interim manager, and which faces an extremely bleak outlook. Such a bleak outlook is solely because of one man and his ideas of roster construction: Dave Dombrowski.

At the same time that the Phillies and their brass were openly wondering what was next for the franchise, the Yankees were preparing to play Game 1 of the ALDS at Tropicana Field, which they lost last night in St. Petersburg. It came in the team’s 34th consecutive winning season and their ninth playoff appearance in the last 10 years.

Despite having a core of older veterans who do have a gradually closing window, like the Phillies, the Yankees found a lifeline in the development of two little-known prospects into the likely AL Cy Young and a slugging first baseman/DH who will get down-ballot MVP votes in his second full season. The much-maligned architect of this entire core, and several before it, is Brian Cashman.

Cashman and Dombrowski have spent a long time as adversaries. While he was no longer in charge, a roster full of players acquired under Dombrowski beat the dynasty Yankees in the 2003 World Series. His next team, the Tigers, beat the Yankees in the postseason in 2006, 2011, and 2012. His Red Sox took out the Yankees in 2018 en route to a World Series. You’d think the guy who has won all these head-to-head battles would be heads and shoulders above, but then you must wonder why he’s had to bounce around so much.

Here, what we really get is two entirely different executives with entirely different philosophies about how to build a contender. Neither has much experience overseeing failure, so the large part of their careers has been defined by their climb toward the top of the mountain.

With Cashman, as we’ve seen for essentially three decades, it’s an approach that is more focused on long-term sustainability. He’s been blessed with the power of working with one of the league’s deepest pockets in the biggest market in baseball, which usually allows him the bandwidth to fill crippling holes. His approach in the offseason is predicated on getting high-end talent on big deals in free agency to flex their financial muscle, but also making shrewd, under-the-radar trades to fill much of the roster.

While he’s willing to shell out for big contracts both via trade and in free agency and absorb the financial risk that he knows ownership can deal with, he’s more measured when it comes to truly taking that next step. You’ll see him balk at an additional year in a free-agent deal or hold onto a top prospect in trade discussions for a top-level talent. There are times this works, but there are also times he’s left at the altar and burned for it. Yoshinobu Yamamoto’s free agency and trade discussions for Gerrit Cole in the winter of 2017 ring a bell for that.

That restraint is based on his belief in long-term sustainability. The Yankees rarely have a great farm system, but if they can produce an era-defining superstar (hello, Aaron Judge), it makes everything drastically different for roster construction. By that note, he’ll always leave holes on the roster to allow for a cheap, homegrown player to fill them. From here, it can go two ways. You can get a Judge and some great complementary pieces on rookie contracts like Gleyber Torres and Gary Sánchez, but you can also get burned by hoarding a prospect in trade talks (Chance Adams, Clint Frazier, Deivi Garcia).

This mentality is completely different than the one you’ll see Dombrowski employ. His approach to roster building, while similarly predicated on a very generous owner with deep pockets, is more based on taking risks in both free agency and the trade market, pursuing as much proven talent as possible. This approach narrows a contention window, but it’s something he’s able to work off of. It’s a lot easier to do your job when you identify a five-year window to win and disregard anything that comes after it.

Looking at how he’s managed this throughout his tenure, he made some gigantic trades and signings to turn Detroit into a perennial AL contender, acquiring Miguel Cabrera from his old stomping grounds in Miami in 2007 and David Price in 2014, while also inking Prince Fielder to a ridiculous nine-year contract. In Boston, he made blockbuster signings in Price and J.D. Martinez while swinging a franchise-altering deal for White Sox ace Chris Sale. In Philly, he’s been more muted, but gave a massive 11-year deal to Trea Turner to solidify the shortstop position. You’re never bored in an offseason under Dombrowski.

This approach is predicated on doing whatever it takes to climb to the mountaintop, looking to increase the team’s chances of raising the Commissioner’s Trophy at least one time by enough that it offsets the losses that will come down the road. It’s risky in a sport that has so much randomness in the postseason, but if it pays off, it’s genius. Just ask the 2018 Red Sox, who proceeded to bottom out in the ensuing two seasons and only make one playoff appearance over the next six seasons, if they’d trade that title for more wins in those lost seasons.

When it doesn’t work? It leads to a lot of resentment. The Tigers won a pair of pennants in 2006 and 2012, but in an extended, decade-long run with the same core of Cabrera and Verlander at the forefront, the Tigers imploded, missing the playoffs in four consecutive years between those pennants and ultimately wound up spending over a billion and burning up the farm system for no World Series. After Dombrowski was dismissed after a terrible 2015 season, the Tigers wouldn’t make the playoffs again until 2024.

The Phillies hired him to be their President of Baseball Operations in 2020, and he did what he does best. He got Turner; he got Kyle Schwarber; he extended Zack Wheeler and Aaron Nola. In lieu of blockbusters, he elected to slowly chip away at the farm depth by making a mountain of smaller moves every winter and summer. It was, honestly, his least all-in job as an executive since he was in Miami, but it’s still leading to the same place as Detroit. He was hailed as a savior in 2022 when the Phils won the pennant, but is now on the verge of being driven out of town as they stare down an unbelievably bleak future without a title to show for it.

The strengths and weaknesses of Cashman and Dombrowski are directly opposite of each other. They show the two ways you can run a perpetual contender. Cashman’s philosophy allows him to keep his job for decades and decades, while Dombrowski often gets canned after the contention window slams shut. You might think Cashman’s job security is a byproduct of organizational complacency, but there’s a reason he’s universally revered for his work in baseball circles.

The two rarely go head-to-head for big signings or trades, but you can imagine how they would go. Dombrowski might give a guy an extra year or two in a deal that Cashman is apprehensive about doing. It could either end up like Yamamoto, where his prime wins you multiple championships, or like Turner, who’s turning into one of the worst contracts in the sport just four years in. In the trade market, Cashman might balk at the asking price for a big-time player, while Dombrowski would go for it. That could lead to a massive success like Sale, or a massive failure like what the Mets did with PCA.

If Dombrowski ran the Yankees over the last 15 years, do we see a World Series? I’m not sure. I’d imagine he’d be much more interested in that mega-deal the Braves proposed in 2014 that would’ve sent Luis Severino, Sanchez, and Judge to Atlanta for a box full of proven talent. He’d also be much more likely to pull the trigger on a Kyle Tucker trade that included Ben Rice in the winter of 2024 or a Eugenio Suarez/Merrill Kelly deal with the D-Backs that would’ve sent Cam Schlittler to the desert.

All in all, as the Phillies enter an offseason where they must consider firmly shutting their contention window, the Yankees not only still have a chance to win this year, but seem to have enough young talent left over to win down the road when Judge and Gerrit Cole hang up their cleats. It’s the latest chapter evolving in the several decades that Dombrowski and Cashman have spent as two of the league’s most famous executives, a chess match to truly decide which is the better style of building a contender.

For the thirteenth time in franchise history, the Giants have ended a regular season with 90+ losses. It’s the tenth time in the San Francisco era where the team has piled up that much losing in a single year and the fourth time in the Oracle Park era. In fact, since 2000, the San Francisco Giants have had fewer winning seasons (13) than winning ones (14). But there were the Bonds years and those three World Championships, so, it’s not like we haven’t been able to enjoy plenty of positives since the turn of the century.

Still, that’s a surprising amount of losing for what’s supposed to be one of baseball’s crown jewel franchises and for a team that touts its desire to remain competitive (while still being financially responsible). The Giants are a money-making business and they’re quite good at making money. Which might explain why the baseball operation doesn’t come off as successful. But maybe that’s all relative?

For one thing, we don’t have to view their two recent 81-81 seasons as bad things. Maybe they’re not technically “winning” seasons, but the Houston Astros just (briefly) made the postseason with that exact record. If that’s now a bar for success, then maybe the Giants have, in some lowered measure approximating respect, managed to have a good amount of success in their waterfront park (15 non-losing seasons to 12).

And for another thing, since this ownership group took control and saved the team from moving to Tampa Bay, they’ve posted the 8th-most wins in MLB with a record of 2,756-2,583 (.516). 9 playoff appearances in 34 seasons. 3 World Championships. Those Bonds year. That beautiful stadium. Jeff Kent is a Hall of Famer. Dusty Baker and Bruce Bochy are headed there, too. Buster Posey, too. Brian Sabean, probably. It has been a really high volume of success. They’re not in the top 3, but they have a good showing on the winning Top 10:

• Yankees: 3,110-2,224
• Atlanta: 2,990-2,346
• Dodgers: 2,987-2,353
• Red Sox: 2,890-2,450
• Cardinals: 2,855-2,480
• Guardians: 2,832-2,502
• Astros: 2,789-2,550
• Giants: 2,756-2,583
• Phillies: 2,710-2,630
• Mariners: 2,681-2,656

The Yankees have stayed The Yankees. The Dodgers are what they are (criminals). Boston broke their curse and basically remade themselves into a topflight organization (though with plenty of behind the scenes drama).

They are the top 3 organizations in the sport. If a fourth team joined them on a Mt. Rushmore, who would be the best fit?

Atlanta raises the question of, “is it better to be in the playoffs every year or is it better to win the World Series a few more times?” because in the span of time when the Giants have been owned by this particular group, Atlanta has won just 2 world championships in 23 trips to the postseason (including the current one). Still, that’s a lot more money each year with postseason revenue…

The Phillies have been chasing their 1 title in 2008 for nearly two decades now. They and Atlanta are also the two losingest franchises (11,457 and 11,096, respectively).

The Guardians sure do win a lot except for when it counts the most. They’ve won just 2 championships and the last one was in 1948.

The Mariners don’t even have the titles under their belt.

There’s nothing genuine about what the Astros did. Lose 100 games for a few years, get some talent, then cheat when the games matter most? Add to that, Jeff Luhnow has been the architect of MLB’s assault on its labor force. Just don’t see how Houston could join those three teams.

This “since 1993” cutoff cuts off the Tampa Bay Rays, who might warrant general consideration.

The Cardinals probably have the strongest claim insofar as they have 11 championships to their name. They have the history and tradition angle. Their stadium’s even a little bit younger than Oracle Park.

But there was a moment in time, alllllll the way back in the 2010s, when the San Francisco Giants had the chance to be one of baseball’s big 4 teams, setup by those 3 titles in 5 seasons along with the ballpark and all the history. That didn’t wind up being the case, because baseball is very hard and the dominant Giants of the past can’t really exist in today’s world, but rather than stumble around for an idea here, let me bring this piece into focus:

Are the Giants losers? Are we rooting for a losing franchise? Have the San Francisco Giants held on to their brief success in the 2010s so hard and so long that they’ve actually become losers? Did they become Al Bundy? It’s entirely possible that Buster Posey stepping into the role of President of Baseball Operations was that particular fever or malaise breaking, but the results haven’t quite followed and really oughtn’t figure to follow — at least in the next couple of years.

They’re still #8 in wins in this Oracle Park era (2,198-2,071, .515) and with three championships, they’re tied with the Dodgers for the moment. Seems impossibly stupid to describe them as losers or even suggest it. I also consider “loser” more of a state of mind or behavioral, and as disappointing (or abhorrent) as the Giants’ behavior has been recently, I’ve got to admit that the winning is strong enough to balance that out to a degree.

But how should we describe this moment in time?

If we chop off the first 10 seasons of Oracle Park history and just look at their record since their dynasty of the 2010s began, they fall to thirteenth in wins (1,343-1,309), in an exact tie with the Chicago Cubs. They’re the last two teams with winning records (.506) in MLB over this span. That’s… remarkable. And shocking. And… not great for a team that won three titles in five seasons.

The Boston Red Sox, who’ve won the most World Series in the 21st century so far, are just #8 in wins (1,401-1,251; .528), but I think that speaks more to the top heaviness that the league has settled into. And that’s not a comment on the league’s financials. Look at the list:

• Dodgers: 1,570-1,082 (.592)
• Yankees: 1,508-1,143 (.569)
• Rays: 1,440-1,213 (.543)
• Atlanta: 1,430-1,220 (.540)
• Cardinals: 1,421-1,229 (.536)
• Brewers: 1,419-1,234 (.535)
• Guardians: 1,403-1,246 (.530)
• Red Sox: 1,401-1,251 (.528)
• Astros: 1,365-1,286 (.515)
• Phillies: 1,353-1,299 (.510)
• Blue Jays: 1,345-1,307 (.507)
• Cubs: 1,343-1,309 (.506)
• Giants: 1,343-1,309 (.506)
• Rangers: 1,233-1331 (.498)
• Mets: 1,318-1,334 (.497)

The list gets even scarier if you just look at their record since the start of 2017. The Giants drop to 18th (736-782, .485). Only two other teams with sub-.500 records are ahead of them: the Mets (758-760) and Dbacks (750-768). The 12 teams with fewer wins since the end of the dynasty: A’s, Reds, Nats, Rangers, O’s, Angels, Pirates, Marlins, Tigers, White Sox, Royals, Rockies. This is a rough group to be a part of and it’s a little surprising that everyone running the team seems perfectly fine with it.

Forget the division. The franchise isn’t even a third Wild Card contender. Baseball keeps lowering the bar and the Giants keep lowering theirs to come up short. And if you think that sounds extreme, since the third Wild Card was introduced for the 2022 season, the Giants are 386-424 (.477) — 21st in wins.

Both John Shea and former site contributor groug have taken a look at the Giants ownership group over the past several years and the two reporters have sort of hit on the same idea: the group is a hybrid of old family money who invested because they’re fans of the team alongside “a sports team is a sensible investment” new money. Has the decision-making of the majority owners become calcified to the point that the demands of the new money sort of even the team out to simply being an extraction business? Are the Giants just in it for the theater and China Basin? Maybe that has always been the case, using the civic pride for the team itself as a wedge issue to get in there and seize valuable Bay Area real estate, greasing the wheels and appeasing any “interest groups” for as long as they’re needed, then discarding when it becomes inconvenient.

So, is this the Extraction Era?

Well, there’s the private financing for the stadium, the $3.37 billion in payroll since 2000 (according to Cot’s MLB Contracts), the Arizona training complex, the improved international facilities… they have invested in the team to a degree. But there’s also Mission Rock. The new money coming in to help with that, even, despite its supposed self-sufficiency. That $3.37 billion in payroll has only amounted to the team being in the top 5 just three times (2015, 2017, 2018).

Again, it just seems odd that a team that has invested so much should come up so short. It has moved beyond disappointment to a real point of frustration. As though it’s just enough money to create the illusion of competitiveness without actually amounting to that. This has truly only been a symptom of the post-championship era, though, which is why I suggested calcification and a de-prioritization of success.

To wit, the pandemic/COVID season really does skew things a bit, but the Giants have never lost so many games (782) in a 1,518-game span… in their history!

Obviously, this stretch isn’t as bad as the 1970s. The Giants traded away Willie Mays in 1972, and from 1972-1985, the team was dreadful, losing 1,165 out of 2,208 games (.472). This is the only span in Giants history where that’s happened. In fact, if you drop the search criteria to a minimum of 1,100 losses out of 2,200 games, this is still the losingest stretch in franchise history. I still need to see the results of 4 more seasons before I can have any room to complain! And I might not even have that “right” in 2031, given that the team won a franchise-record 107 games… and my personal assurance that the team will be competitive again in 2030.

But, also, the team has the #1 rated farm system at the moment. 2030 might be a little conservative. This enterprise could turn around well before then. And I can’t help but note that I can throw in positives no matter how much history I cite. Maybe this agonizing over the team being one of the worst in the sport for most of the last decade and a decent chunk of the century is entitlement.

Sure, we watch sports to be entertained. But if we’re following them every day in a six-month season, aren’t we also doing so to watch peak performance along with the thrill of victory? I’m not sure what the value proposition is with professional competitive live sports beyond that. I guess I’m mentioning this because a criticism of people who wonder about the team’s track record is that it sounds like entitlement.

It just seems to be getting more difficult with each passing year to play the “wait ‘til next year”/“hope springs eternal” card. Year after year, the Giants have managed to tack on as a sort of drag coefficient something to make the disappointment of the season sting a little worse. This year, it’s pretty obvious. That terrible record and all those injuries were made worse by the bigotry. They let down a significant number of fans with that loser behavior. But maybe that’s not the first time something like it has happened. The Giants were probably worse to their fans in the 70s, since everything about the Giants in the 1970s was worse than today, apparently.

But there were plenty of verifiable firsts, things I’d never think would happen: the first time the Giants have gone five consecutive seasons without a plus-.500 record. Or, to put it another way: the first time they’ve lost 80+ games five years in a row. The first time in over 120 years that they’ve ended a season trailing the Dodgers in their now-dead rivalry by 2 games. The first time they blew a 6-run lead in the ninth inning. The first time they offered to pay their fans to attend games in the final month of the season.

It’s unclear what sort of an organization it is that they’re trying to build or maintain. As a money-making enterprise, it’s very clear. Leverage the Giants brand to expand the investments in real estate. Or simply follow as closely as possible the Peter Ueberroth guide to sports business:

“Let’s say I sat each of you down in front of a red button and a black button,” he said at one early meeting. “Push the red button and you’d win the World Series but lose $10 million. Push the black button and you would make $4 million and finish somewhere in the middle.”

He paused to look around. “The problem is, most of you would push the red one.”

Ueberroth chided them for checking their business sense at the door. “You are so damned dumb.”

But what about the baseball operation? It has certainly tested the idea of “somewhere in the middle.”

In the Magowan-Sabean days, the goal was clear: build a competitor that could win a World Series. That’s hadn’t been done before in San Francisco. There doesn’t seem to be that sort of urgency from the organization today and certainly no obvious expertise on which to hitch your hopes. The recycled “Nothing Like It” slogan is pretty telling on that front, I’d say. A lot of half-hearted stabs in the dark at finding the next “thing” that might redefine the team’s identity but otherwise being fine with the decaying state of things.

Under ideal circumstances, teams are able to reinvent themselves by investing in their player development system. With enough time and some luck, a perpetual motion machine provides talent to the major league roster at a low cost. What has happened, though, is that the real estate business jockey that has been riding the horse that is the baseball club has created a perpetual motion machine of real estate investment.

I have often wondered if there’s a situation where the Mission Rock contingent buys up enough of San Francisco that they eventually sell the Giants and rent the stadium back to its new owners, like what Frank McCourt did when he sold the Dodgers but kept the parking lot.

Anyway, call this era what you want, but it’s composed of a lot of losing. A lot of failed attempts at returning to relevance, too, though. Ownership got what it wanted, but we root for the team because we’re interested in seeing them win, not watching their ownership expand their portfolios. But that seems to be the only upside for the business these days. The front office seems out of their depth and none of the public-facing figures are a good quote, a positive presence, or inspiring of confidence. Winning can usually flip perception 180 degrees within just a single season, but we haven’t seen the San Francisco Giants win in a long time.

As we all process our playoff anxiety for the day, let’s look at some keys and prominent storylines for the Guardians-White Sox ALDS Game Two at 5PM ET today.

Top Storylines:

-Anthony Kay and Sean Burke have dominated the Guardians this season (1.35 ERA for Kay, 1.04 ERA for Burke). Can the Guardians get to them?
-Will Gavin Williams be negatively affected by a lengthy layoff?
-Will the afternoon shadows surpress offense at the beginning of the game?
-Will Game Two be a sellout for the Guardians as fans struggle to get time off work and deal with turbulent economic times (plus, perhaps playoff burnout?)?

Keys for a Guardians’ Victory:

–Hit Burke’s fastball/cutter combination. This season, Burke has thrown the Guardians 98 four-seamers allowing a .278 wOBA, 45 cutters allowing a .077 wOBA, 27 sinkers allowing a .787 wOBA, and 59 sliders allowing a .318 wOBA. The Guardians who have hit him decently: Austin Hedges 1.164 wOBA, Petey Halpin .890 wOBA, Steven Kwan .508 wOBA, Patrick Bailey .445 wOBA, Brayan Rocchio .334 wOBA, and Chase DeLauter .318 wOBA. If the Guardians want to win, they need to be ready to hit Burke’s four-seamer which is gonna be their steady diet today. He doesn’t have a changeup, Guardians. Take solace in that.
–Finally get to Anthony Kay. They, somehow, haven’t done it yet this season. Now, Kay is going to be more effective in shorter stints, like most pitchers, but he does have a 4.44 ERA and a 4.75 FIP. Those are not good numbers. The Guardians’ lefty-mashers – Chase DeLauter, Jose Ramirez, Jo Adell, David Fry and Angel Martinez – are going to need to go into this game ready to put up a good at-bat and do damage on pitches to hit. If they don’t make Kay’s life tough in the first or second inning, I don’t like their chances to win this game.
–Gavin Williams Needs to Make Effective Strikeout Pitches. The White Sox managed to bug Williams by spoiling third strike pitches over and over the last time out. Gavin, trust your stuff, maintain a consistent delivery, and go after these dudes because it’s basically now or never.
–Vogt, Don’t be Afraid to Use Foster Griffin. If Williams runs into some trouble in the fourth or fifth, the White Sox will have a lineup with a good amount of lefties. If Griffin can pitch without running into Miguel Vargas right away, today is a good day to let him use his groundball abilities and lefty-neutralizing skills to your advantage. They’ve seen Herrin and Sabrowski a LOT this year. Let Griffin help.

Overall, the Guardians need to remember that this is YOUR homefield and YOUR division. Come out with a consistent approach at the plate, forcing the pitchers to be in the zone and taking advantage of any pitch to hit you see. I’d predict that if they don’t manage to take at least four walks and hit at least one home run, they will not head to Chicago with a win in hand. But, they’ve got the talent and the experience to redeem a disappointing game one loss. Let’s root them on to make it happen!