On paper, that’s a quality nine. You have Moncada and Anderson, each coming off breakout seasons. You have Abreu and Encarnacion, two elder statesmen who have been reliably above-average hitters. You have Grandal, one of the best catchers in the game. You have Jimenez and Mazara, two corner outfielders with middle-of-the-order pedigree if not track records. And you have Robert and Madrigal, two top prospects who haven’t yet debuted.
On Wednesday, the Chicago White Sox reportedly agreed to terms with free-agent designated hitter Edwin Encarnacion on a one-year deal worth million. (The pact includes a club option, too.) While we have concerns about Encarnacion’s barrel control heading forward, the White Sox now have the potential to field a strong lineup with Encarnacion and fellow free-agent addition Yasmani Grandal in the middle of it.

  1. 3B Yoan Moncada
  2. SS Tim Anderson
  3. 1B Jose Abreu
  4. DH Edwin Encarnacion
  5. Yasmani Grandal
  6. LF Eloy Jimenez
  7. RF Nomar Mazara
  8. CF Luis Robert
  9. 2B Nick Madrigal

Of course, the White Sox might opt to take a different route — the one they did with Jimenez, who signed a long-term extension before he debuted. Whether Robert and/or Madrigal would be game for a similar arrangement is to be seen. But the White Sox have added a lot of talent to their roster this winter, and it would be a shame if they don’t use run out their best lineup possible on Opening Day.
This is the same thing the Chicago Cubs (with Kris Bryant), Atlanta Braves (with Ronald Acuna Jr.), and Toronto Blue Jays (with Vladimir Guerrero Jr.) have done in recent years. To run through the talking points: yes, basically every team does it; no, that doesn’t make it OK; yes, the rules needs to be altered so they don’t incentivize service-time manipulation in the name of savvy roster-building; no, that doesn’t make it OK, either.
The date of those debuts will be one of the bigger storylines heading into the season for the ChiSox. What the organization decides to do with Robert and Madrigal’s debuts will be notable in part because it will answer whether the White Sox prioritize winning as many games as possible to manipulating service time. The lineup card could look something like this next summer on the South Side:
There’s a chance — and you never know how these things will work out — that both Robert and Madrigal receive consideration for the American League Rookie of the Year Award. We ranked them No. 1 and No. 4 in the White Sox system earlier this year. We wrote that Robert has “the potential to be a middle-of-the-order hitter who can hang in center field during the early stages of his career.” As for Madrigal, we noted that he’s “a good defensive second baseman with absurd bat-to-ball skills who ‘runs like a [mother’s intimate friend],’ in the words of one source.” 
These arguments are at their most frustrating when it involves a team like the White Sox, who aren’t clear favorites to win the American League Central. The division could be decided by a game here or there — perhaps one that the White Sox lose because they opted against fielding their best team in the name of saving money down the road. And that’s what it comes down to: teams can almost always extend team control with a player by offering a fair extension before they hit free agency — they are limited only by their inherent opposition to paying market price.
Because the White Sox seem intent on contending in 2020, it stands to reason they’ll want Robert and Madrigal in the lineup as often as possible. That probably rules out keeping the pair in the minors into the summer in a craven attempt to avoid Super Two designation. (Read: a fourth year of arbitration.) We’re not as quick to dismiss the possibility of the White Sox holding down both for a couple of weeks, resulting in Chicago gaining an additional year of team control.