yasmani grandal
Hahn’s gambit had failed. Oh, and the prospect they gave up? Fagerstrom described him as follows, reflecting industry consensus at the time: “A total wild card. Could be a future All-Star. Could be a future zero.”

Three years later, Fernando Tatís was the no. 2 prospect in baseball. As a 20-year-old rookie shortstop with the Padres, he was worth 4.2 bWAR in half a season and hit .317/.379/.590. No White Sox shortstop has ever had such a strong batting line in any season, at any age.

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Tatís looks like a future MVP candidate, and he’s leading a renaissance in San Diego, where the sport’s top-ranked farm system as of last spring is churning out prospects to populate the next Padres contender. But back in his old organization, the White Sox are charting a similarly optimistic course, led by a prospect surge of their own.

And they’re acting like contenders, too. The White Sox committed $151.5 million in free agency this winter, fourth most in the majors. Only the teams that signed the three top free agents—the Yankees with Gerrit Cole, the Nationals with Stephen Strasburg, and the Angels with Anthony Rendon—spent more. Chicago’s prospects are poised to reach the majors, or already here. Proven veterans are joining in support. The White Sox are angling for their first playoff berth in more than a decade, and they’re illustrating why the best path to winning is development plus spending—not just one, not just the other.

If June 2016 represented Chicago’s quiet low point, December 2016 represented the loud start of a new chapter for the franchise. In the span of two days, Chicago traded ace Chris Sale, who was signed to a cheap long-term deal, to Boston in return for prized prospects, and leadoff hitter Adam Eaton, also signed to a cheap long-term deal, to Washington in return for yet more prized prospects.

The sale continued through the next summer. The White Sox traded José Quintana—who, surprise, was also signed to a cheap long-term deal—to the Cubs in return for—again, surprise—more prized prospects. They traded veterans like Todd Frazier, David Robertson, and Anthony Swarzak. And then they sat, and waited, and waited some more for the next generation of competitive White Sox players to arrive in the majors.

In the meantime came a lot of losing, a lot of Remember Some Guys starts from the likes of Derek Holland and Mike Pelfrey, and a lot of uninspiring play in the worst division in the majors. The team’s home attendance dropped more than 7,000 fans per game compared to the start of the decade, and more than 11,000 fans per game compared to the last time it made the playoffs.


But after the sustained losing, the 2020 season promises something new for White Sox fans: hope. And not just in the standard spring training kind of way, either—objective numbers inspire hope, too. Projections from FanGraphs and Baseball Prospectus estimate the White Sox at 83-84 wins this season, and about a 20 to 25 percent chance of reaching the playoffs. Public projections have never been this high on the club. (This graph includes an assemblage of preseason projections dating back to 2005, originally collected by former FanGraphs writer Jeff Sullivan.)


Before the White Sox make a run at relevance, it’s worth analyzing the path they traveled to this juncture, and how it reflects the multifarious ways to build a winning roster. Of the 15 White Sox projected to produce at least 1 WAR this season, per FanGraphs, only two were in the organization back in 2016, when Hahn initiated the rebuild. José Abreu was already an All-Star first baseman, after signing out of Cuba before the 2014 season, and shortstop Tim Anderson debuted in the majors that year, after joining the franchise in the first round of the 2013 draft.

Yet 13 of the 15 top players are more recent additions. They separate into three methods of acquisition: fully internal prospects, prospects acquired externally, and major leaguers brought in from other teams.

The Internal Prospects
Two of the 13 players of note have never played for another organization, joining the White Sox when they entered the MLB ranks and rising through the farm system. Chicago signed center fielder Luis Robert out of Cuba in May 2017 and drafted second baseman Nick Madrigal fourth in June 2018.

This is the first group that comes to mind when contemplating a full-scale rebuild: Pick at the top of the draft for a few seasons, invest in international free agency, and wait for the new prospects to matriculate to the majors.

Other successful rebuilds relied on such internal development to produce future MLB talent. The Cubs picked in the top 10 of the draft every year from 2011 to 2015, and the first four players picked that high all contributed to their World Series–winning team in 2016: Javier Báez (ninth), Albert Almora (sixth), Kris Bryant (second), and Kyle Schwarber (fourth). The Astros, meanwhile, were the sport’s worst team three years running and drafted Carlos Correa no. 1 and Alex Bregman no. 2; they also had future stars like José Altuve, George Springer, and Dallas Keuchel already in the organization from previous drafts and signing periods.

The first such player for the White Sox, Robert, might be the favorite to win this year’s AL Rookie of the Year award, after completing a 32-homer, 36-steal, 1.001 OPS season in the minors in 2019. He already projects as slightly more valuable this year than established outfielders such as Austin Meadows, Marcell Ozuna, and Starling Marté.

Unlike Robert, Madrigal and his unprecedented contact skills won’t be in Chicago’s lineup on Opening Day, but he should receive a promotion before long. Other White Sox draftees could help the club soon, too. First base prospect Andrew Vaughn, the no. 3 pick last June, swings a mighty bat, though his rise to the majors might be delayed because Chicago’s first base and DH spots are already filled.

But only a small portion of Chicago’s roster started with the organization. Aside from Anderson, the club’s earlier drafts largely failed to add future contributors. And in a draft as uncertain as baseball’s, where fewer than half of players picked in the first round last three seasons in the majors, it’s impossible to build a contender through this method alone.

The External Prospects
Six of the 13 fit this group, which comprises players traded to Chicago when they were still prospects: infielder Yoán Moncada, outfielder Eloy Jiménez, and starting pitchers Lucas Giolito, Reynaldo López, Michal Kopech, and Dylan Cease.


This is the second group of players commonly associated with a rebuild—trade every veteran star for future production and hope all the new prospects coalesce for a contender some three to five years down the line.

The six players here came to Chicago in those three trades, two at a time: Moncada and Kopech from Boston for Sale, Giolito and López from Washington for Eaton, and Jiménez and Cease from the Cubs for Quintana. They were all relatively advanced in the minor leagues at the time, and they all ranked as top-100 prospects, too: Before the 2017 season, Baseball America ranked Moncada second, Jiménez 14th, Giolito 25th, López 31st, Kopech 32nd, and Cease 97th.

Because of Chicago’s commanding starting position, with three desirable players on three desirable contracts, the White Sox benefited especially from this method of team building. Since they weren’t dealing rentals, they could ask for a host of top prospects to replenish a farm system that consistently ranked near the bottom of the league. Before 2017, Chicago didn’t have a top-10 farm system, as rated by Baseball America, since 2002; they’ve been that high every season since.


If the White Sox are to contend in 2020, the players in this group will play a major role. Moncada led the club in batter WAR last season, as he finally hit like a former top prospect after two mediocre campaigns. Jiménez quietly batted 25 percent better than the league average after the All-Star break as he adjusted to MLB pitching in his rookie year. And the young hurlers, led by 2019 breakout Giolito, can fill out the rotation with upside.

An enviable farm system is not itself a complete recipe for success, however. The White Sox themselves learned this lesson the last time they boasted a strong prospect crop. Baseball America rated Chicago’s farm system no. 1 in 2001—but the club’s top 10 prospects that year averaged just 2.3 WAR with the team. Aaron Rowand and Joe Crede were decent contributors; Jon Rauch, Joe Borchard, Matt Ginter, Dan Wright, Lorenzo Barceló, Brian West, Josh Fogg, and Jason Stumm all busted.

Prospects in general bust; it happens. Which makes the third bucket of players all the more important.

The External Major Leaguers
Five of the 13 fit this final category: players who were already established big leaguers when they joined via free agency or trade. Catcher Yasmani Grandal, first baseman/designated hitter Edwin Encarnación, and starting pitchers Dallas Keuchel and Gio González signed with the club this winter, while outfielder Nomar Mazara came to Chicago in a trade for 2018 second-round pick Steele Walker.

Grandal projects as the club’s best player in 2020, and the best catcher in the majors. He should provide a boost on both sides of the ball; his bat rates as the best among catchers in the past three seasons (min. 750 plate appearances), and his glove is even more valuable, with excellent pitch framing metrics throughout his career.

The White Sox have consistently ranked toward the bottom of the league in framing; Grandal has consistently ranked toward the top. The stats suggest he’d add four runs worth of value over previous Chicago backstops from stealing strikes alone.


It’s possible Grandal’s skill in this area could have a compounding impact with fellow signee Keuchel on the mound. In the past three seasons, 46 percent of Keuchel’s pitches have landed on the edges of the strike zone—the second-highest rate out of 115 pitchers with 5,000-plus pitches in that span. He and Grandal could form the perfect pairing, targeting corners all game long—to say nothing of Grandal’s ability to make life easier for all the young Chicago pitchers learning how to navigate MLB lineups.

The other newcomers are known quantities, too. Encarnación is good for 30-plus homers in the middle of the order every season. González has posted an average or better park-adjusted FIP every season since his rookie campaign of 2008. Mazara at the very least adds a platoon bat to a barren outfield—and, entering his age-25 season, still might tap into further upside, too.

The narrative around rebuilds often focuses on the first two methods of player acquisition—what happens while a team is in the throes of losing—ahead of the third. But from past successful turnarounds, it’s clear the third is just as vital, particularly when those moves are timed for when the young talent begins to consolidate at the MLB level.

Looking at just the two most recent examples, the Cubs have infamously failed to develop pitchers under the current regime, so they needed to sign Jon Lester and John Lackey in free agency. World Series MVP Ben Zobrist was also an addition in free agency, as was most valuable motivational speech-giver Jason Heyward.

The Astros, meanwhile, weren’t fully actualized as a championship contender until they traded for Justin Verlander and Ken Giles, and added complementary veterans like Brian McCann, Josh Reddick, and sign-stealing architect Carlos Beltrán. And though they haven’t won another title since 2017, the Gerrit Cole trade before the 2018 season certainly helped Houston remain the league’s most imposing club.

Because many young players fail to maximize their potential, veteran supplements are crucial, even if they’re priced higher (or just more fairly) than cost-controlled players early in their careers. Grandal signed the largest contract in White Sox franchise history, at four years and $73 million—but from the perspective of a dollars-per-WAR model, Grandal was underpaid every season of his career.


Even on his White Sox deal, Grandal still projects in the range of twice as valuable as his salary suggests. This chart estimates Grandal’s value through the next four seasons using a simple aging curve (losing half a win per season) and the cost of a win in free agency, about $9 million.

A veteran’s contract doesn’t need to be a steal for him provide value to the club, either. Keuchel, for instance, will receive $54 million over the next three seasons—and that value estimation method predicts he’ll be worth the same $54 million in that time. There’s no “extra” value on his deal.


But the White Sox aren’t counting on him to repeat his 2015 Cy Young–winning season; they just need reliable innings from a mid-rotation arm. Keuchel is fit for the job, having missed time for just one injury in his career, when a pinched nerve in his neck cost him two months of the 2017 season. Other White Sox like Kopech might have a higher ceiling than Keuchel at this point in their respective careers. But after the 2019 White Sox needed to turn to a bevy of unqualified starters last season, Keuchel—or any other starter who can throw five innings without tripping on the mound—will be a welcome presence in the rotation.

Had all of Chicago’s prospects panned out, Grandal, Keuchel, and others might not be needed. But no farm system survives intact. Prospects might not advance as quickly as anticipated; Blake Rutherford, for instance, was the headliner when the White Sox traded Frazier, Robertson, and Tommy Kahnle to the Yankees in 2017, but he posted a below-average batting line at Double-A last season.

Prospects also might stall due to injuries, and Chicago has experienced its share of prospect attrition more for injury reasons than a particular problem with talent evaluation. The White Sox’s first draft pick post-sale (or post-Sale) was third baseman Jake Burger, who’s missed the past two full seasons after tearing his Achilles twice. One of their 2016 first-rounders, reliever Zack Burdi, needed both Tommy John surgery and knee reconstruction surgery. Both Kopech and pitching prospect Dane Dunning—another player in the Eaton trade, who made subsequent top-100 lists—have needed Tommy John surgery as well; so has 2014 first-rounder Carlos Rodón, who’s never managed to harness his immense potential and now has to rehabilitate from his procedure.


Chicago’s predecessors have also confronted this dilemma. From 1965 (the start of the MLB draft) through 2012, only two no. 1 picks never played in the major leagues. Then the Astros whiffed on two top picks in a row, taking Mark Appel first in 2013 (ahead of no. 2 Kris Bryant and no. 3 Jon Gray) and Brady Aiken in the same spot the next year. Had Appel, who has already retired without making the majors, and/or Aiken—who didn’t end up signing with Houston due to a medical scare, and has since stalled in the low minors with Cleveland—worked as intended, Houston might not have needed any pitching upgrades in August 2017. Instead, they traded for Verlander, and won a title as a result.

The White Sox still have plenty to prove to reach the Astros’ level pre-Verlander. They won just 72 games last season, yet somehow overperformed their run differential; they ranked 24th in runs scored per game and 22nd in runs allowed. And White Sox optimists have been premature before; at the start of the 2018 season, Rany Jazayerli wrote for The Ringer that the club’s rebuild “may pay off even sooner” than anyone expected. Then Giolito was the worst qualified starter in the majors, multiple prospects suffered debilitating injuries, and Chicago finished the season with 100 losses, the franchise’s worst mark since 1970.

Fool us twice, shame on us—but the situation really looks different in 2020, and not only because Detroit and Kansas City remain terrible and Cleveland seems more inclined to trade all its best players than try to contend. The roster also oozes talent, and the players seem to fit together in a sensible manner. No squinting is required to see a viable lineup, with Abreu and Jiménez and Encarnación driving in Robert and Moncada and Madrigal. And while the pitching staff inspires concerns about youth and injury histories, only one other youngster needs to take a leap alongside Giolito to give the White Sox a formidable rotation.

Moreover, Chicago is planning for the longer term beyond 2020. The Grandal and Keuchel contracts extend four and three years, respectively; Encarnación’s is only one year because he will presumably be supplanted in the lineup by Vaughn next season. And the front office has proactively extended Moncada, Jiménez, and Robert to ensure continuity for years to come. (For the latter two, the extensions came before either player had even been promoted to the majors. Perhaps the White Sox were taking advantage of their leverage in potentially holding the top prospects down to manipulate their service time, but at least those deals reflect market value better than others offered to pre-MLB players.)

Chicago has made mistakes along the way, of course. The Tatís trade is already a disaster of epic proportions, and will grow even worse with every All-Star-caliber season the young shortstop plays in San Diego. Every team makes poor decisions and lousy internal evaluations on occasion. But that’s where external additions and money can help fill in the gaps—and Chicago is poised to spend roughly $35 million more on its Opening Day roster this year than last, and more than $50 million more than two years ago.

In a market the size of Chicago, there’s still room to grow, and the White Sox should commit the resources they need to fully compete. They might still need their Verlander at the trade deadline, or their Zobrist next winter, depending on how this season goes. But the darkest part of the rebuild is past, and the club’s future looks brighter than it has in years. The White Sox seem to know it, too, and began acting accordingly this winter. They’re poised to contend with an exciting young roster. Now they just have to start winning the actual games.

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