Chicago White Sox

But after nearly a decade of rebuilds, reboots, and recriminations, it’s finally safe to believe: The Chicago White Sox will make the playoffs in 2020.

“Success to me is the playoffs. That’s the real season,” says left-hander Dallas Keuchel, who signed a three-year, $55.5 million contract with the club this offseason. “If there’s no playoffs, I can’t deem this season a success.”

In 2012, it didn’t seem like the White Sox were headed for the full-scale teardown. That team had a few aging pieces—six of their seven most valuable position players, by bWAR, were at least 30 years old—but there were reasons to be excited about the future. The 2012 season was the first full spin in the rotation for a pair of homegrown 23-year-old left-handers, Chris Sale and José Quintana, and the AL Central–leading Tigers were starting to show their age as well.


But in 2013, after the White Sox signed Sale to a team-friendly five-year extension, they lost 99 games. That winter, they inked vaunted free-agent slugger José Abreu, traded for outfielder Adam Eaton, and signed Quintana to a five-year deal with two team options. In 2014, Sale, Eaton, and Abreu (all 27 or younger) each posted five-win seasons. The White Sox lost 89 games. The following offseason, Eaton got his own five-year extension and the Sox flipped promising shortstop Marcus Semien and three other players to Oakland for veteran starter Jeff Samardzija. In 2015, Samardzija allowed more hits and earned runs than any other pitcher in baseball, while by 2019, Semien had blossomed into an MVP candidate.

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Finally, in 2016, the White Sox blew up their homegrown core, shipping Sale to the Red Sox for a package centered on infielder Yoán Moncada, the no. 1 prospect in baseball, and Texan fireballer Michael Kopech. Eaton was traded to Washington for pitching prospects Lucas Giolito, Dane Dunning, and Reynaldo López. And the following summer, Quintana moved north to the Cubs and the Sox received four prospects, including slugger Eloy Jiménez and pitcher Dylan Cease, in return.

These prospects, in addition to recent top-10 picks like Carlos Rodón and Carson Fulmer, gave the Sox an unbelievable bounty of potential stars who were either immediately ready to contribute at the big league level or close to doing so. In February 2017, I wrote that enterprising gamblers would be wise to plop a few bucks down on the Sox to win the World Series at 300-to-1 odds, the longest in baseball, on the off chance that all of those prospects contributed right away.

The White Sox lost 95 games that year, 100 in 2018, and 89 in 2019.

There are two reasons that trend will come to an end this year. You can find one on the walls of the team’s Glendale, Arizona, spring training clubhouse. There hangs a series of jerseys sporting football player numbers: No. 74 for Jiménez, no. 84 for Cease, no. 88 for Luis Robert, no. 92 for Nick Madrigal, and no. 94 for Andrew Vaughn.

This team has been catastrophically bad for seven seasons in a row, and that has provided the Sox with plenty of high-level draft picks. They also sold off three star players who were locked into contracts that massively underpaid them at the peak of their powers, which netted Chicago some top prospects. All together, the Sox have piled up a humongous collection of talented youngsters, and that’s the reason the team’s future looked so bright two or three years ago—even if that promise didn’t translate immediately into success.


And to be clear, the White Sox have had more than their share of developmental misses. Fulmer and 2016 second-rounder Alec Hansen flashed great stuff, but forgot how to throw strikes. Rodón, Kopech, Dunning, and 2017 first-rounder Jake Burger have all lost entire seasons to injury. López looked like he had the makings of a solid mid-rotation starter in 2018 before he fell off a cliff in 2019.

But last year, on balance, things started to break right for Chicago’s homegrown players. Giolito went from the worst pitcher in baseball to one of the best. Moncada started making more and better contact, ended up grabbing MVP votes, and—like Sale, Eaton, and Quintana before him—signed a five-year contract with team options. Shortstop Tim Anderson, himself a former first-round pick, had an enormous season. After two and a half seasons of almost never walking and hitting far too little to get away with it, Anderson had a monster 2019. He batted .335, tops in the AL, to go with 18 homers and 17 stolen bases, and he demonstrated an infectious intensity that made him one of the sport’s most notable and outspoken rising stars.

“I just learned what type of hitter I was, what I could really do in the box, and how dangerous I could really be,” Anderson says of his breakout season. “Now I think it’s just about polishing up the things that I can do and not worrying about the things I can’t do, building that confidence, and feeling unstoppable. I felt that way last year, so I’ve just got to keep that same mentality and it’s going to happen.”

For 2020, Anderson is working on refining his approach to identify and attack pitches he knows he can hit, which will be important, because both he and Moncada benefited from what seems like unsustainable batted-ball luck last season. Moncada finished 2019 with the second-highest BABIP of any qualified hitter in the expansion era, and Anderson had the sixth highest.

That doesn’t mean their respective breakout seasons were a fluke, however. Both players run well, hit the ball hard, and hit a lot of ground balls and line drives rather than fly balls. That kind of hitter is naturally inclined to post high BABIP numbers—Christian Yelich is the most extreme recent example, though Trea Turner and Whit Merrifield also fit the bill—and Moncada, 24, is still developing as a big league hitter.

Plus in 2020, they won’t have to carry the offense all on their own: The next wave of prospects is here. Jiménez hit 31 home runs as a rookie last year, and Zack Collins, a catcher who went no. 10 in 2016, made his debut late in 2019. On Baseball Prospectus’s top 101 prospects list from this past winter, Chicago had four players in the top 31: Robert, Madrigal, Kopech, and Vaughn. Those four also landed in the top 41 at FanGraphs.


Kopech, who famously hit 105 miles per hour on a radar gun while in the Red Sox system, made four starts in 2018 before missing all of last year with a torn UCL, but he’ll make his Cactus League debut this week. Cease had a rough rookie year, recording a 5.79 ERA in 14 starts, but he’ll also have an opportunity to rebound this year. Keuchel, who saw quite a few top pitching prospects during his time with the Astros and Braves, is particularly optimistic about those two having the same kind of breakout season Giolito had last year.

“Gio had a huge year last year. It was a big step, his welcome to the big leagues party,” Keuchel says, “and I’m hoping Cease can take that step as well. And when Michael gets fully cleared—I think he’s only got 14 big league innings, but it seems like he’s had a lot more than that. So I’m hoping that those two guys will take the next step. It’s a process—we’re not expecting them to just bust down the door. But at the same time they have all the stuff in the world.”

Those pitchers are talented—Kopech in particular—but they pale in comparison to the strength of Chicago’s homegrown position players. Starting with Anderson in 2013, the White Sox have used eight consecutive first-round picks on college players, which means their farm system has received a recent infusion of polished, near-big-league-ready talent. Vaughn, the no. 3 pick in 2019, was one of the best college hitters of the 2010s and likely won’t hit the majors for another year, but Madrigal is just a year and a half out of Oregon State and he’s ready now.

Madrigal is already one of the best contact hitters in baseball—he struck out just 37 times in three college seasons and just 21 times in his two professional seasons. Last year, he hit .311/.377/.414 with 35 stolen bases across three minor league levels, and he could very easily start the season as Chicago’s everyday second baseman if the White Sox weren’t interested in keeping him in the minors to delay his free agency.

The one question for Madrigal, who is 5-foot-7, is power. Short, contact-oriented infielders are a dime a dozen, but unlike Bo Bichette, Alex Bregman, or José Altuve, Madrigal is built more slightly and has never exhibited plus power before. Nevertheless, he’s not concerned with bulking up and swinging for the fences—he believes his hit tool is good enough to carry him. “It’s gotten me this far in my life, so I’m not going to try to change it no matter what,” Madrigal says. “No matter if, you know, the game is leaning more towards home runs, I’m going to focus on my game. And I’ve always been that way.”


But the real standout prospect is center fielder Luis Robert, who signed a six-year contract worth $50 million guaranteed this winter despite never playing in the majors. There’s a reason for that. The White Sox already paid a $26 million bonus to sign Robert out of Cuba at 19 years old in 2017, just before the current international bonus rules came into force. Since then, he’s developed into a five-tool monster, a potential future MVP whose combination of power and graceful athleticism generates commentary that goes something like, “I know we’re not supposed to compare prospects to Mike Trout, but … ”

“Unbelievable,” Anderson says of his two rookie teammates. “Luis Robert’s coming in and can do everything. You can’t go wrong with him. And you’ve got Madrigal, who’s going to be up there soon, who’s going to hold down second base and is going to be great for us. Soft hands and obviously can hit as well. So I’m excited to see these guys come up.”

When Madrigal gets his first big league action, the White Sox will be able to field a lineup with three top-20 draft picks and three former global top-10 prospects, all 26 years old or younger. Now that Anderson, Jiménez, Robert, Moncada, and reliever Aaron Bummer are all locked up on the cheap through at least 2024, the White Sox have their homegrown core. And unlike in years past, when the team tended to stay in the bottom third of the league in payroll, Chicago has brought in some hired guns to fill in the holes.

The White Sox missed out on the absolute top-end free agents this offseason, but they’ve spent wisely and aggressively on the second tier. Chicago signed four All-Stars this winter: Keuchel, Gio González, Edwin Encarnación, and Yasmani Grandal. Add Steve Cishek to that mix, and the franchise has committed $58.5 million this year to free agents from outside the organization. The effect of these moves on clubhouse expectations is noticeable.

“It definitely shows us which way the organization wants to go,” Anderson says. “It shows we’re ready to move forward on winning … Keuchel, Grandal, and Gio, guys like that have experience in the playoffs and have won championships. Then you know it’s time to go.”

It also creates a stark contrast to the ever-rebuilding Tigers and Royals, and the Indians, who are in the process of dismantling their own championship contender.

“Try and look at a five-, seven-year window and say, ‘Who’s really going to take this division?’” Keuchel says. “You can’t really say the Indians are in a good spot. It’s like they don’t want to pay their really good players. They could have a really, really good team and they have had a really good team. But I think the White Sox are in a position to push that envelope and be that headlining team in, hopefully, the next five, six years.”

Even if the Indians continue to slide, it will take some work to knock over the Twins, who won the division last year in a walk and reinforced their squad this offseason by adding Kenta Maeda and Josh Donaldson. But overtaking Minnesota is a much easier path to the postseason than trying to overcome an oxygen-sucking juggernaut like the Dodgers or Yankees, or surviving the four-way Grand Guignol that is the NL East. After years of false dawns and frustration, the pieces have finally come together for the White Sox—and their path to the playoffs is clear.

“I’ve always been ready,” Anderson says. “I’ve been ready since I got called up. I’ve just been waiting on my moment to have that playoff push and hopefully go win a championship. I feel like it’s coming, and we’re ready. We’re all in.”

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