Sox Drawer Q&A: Is this the White Sox ‘Jon Lester' offseason?

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Back for another round of questions here in the Sox Drawer. Let's go.

Q: Do you believe this is the Sox "Lester" offseason where they make a large investment in a player for the future? Or are we still one year away from seeing this? — @BCurley3

CG: That's a question many White Sox fans are wondering about. And by the "Lester" signing, I assume you are referring to the likes of Manny Machado or Bryce Harper. I'd like to think that if the White Sox have a desire to sign a big-name free agent, they will make every attempt to do it now and not wait for the 2020 free agents, even if it's coming off a 100-loss season. As general manager Rick Hahn put it in his season-ending press conference, "You can't always control when certain players become available. You can say in 2020 or 2021 we expect to be this, and we know we are going to need X. You can't look at the projected free agent and say that player will be available, much less that player will be a White Sox when the time comes." It might turn out that the White Sox don't sign that marquee free agent this offseason, but going off what Hahn said, I believe they will go all-in when their targeted "Jon Lester" is available.

Q: If you had your choice, would the White Sox sign Manny Machado or Nolan Arenado? — @Dehhmac_

CG: I'll take either. Arenado gets the edge defensively. Machado has the advantage offensively. One stat about Arenado that gives me some pause is his career home/away splits. At Coors Field, he's slashing .320/.374/.609. Away from Coors Field, he's at .263/.318/.469. He's still a great player, but his numbers are inflated due to the higher elevation in Denver. If they don't sign him to a contract extension this winter, I'm curious to see if the Rockies listen to trade offers during the Winter Meetings like the Orioles did with Machado last year. The Rockies are much more competitive than the Orioles, so they might decide to go for it one more time with Arenado. If not, a crazy Winter Meetings just got crazier.

Q: I have long expected this to be the offseason when the Sox start signing free agents. However, lately, I've heard about possible big-name trade potentials. Do you expect trades this early in the rebuild or mainly acquisition through free agency? — @ToddHertz

CG: At some point, the White Sox will probably dip into their farm system to acquire major league upgrades where they see fit. Because there were so many injuries to prospects last season, I'm not sure they've seen enough to know exactly what they have to make those kind trades just yet. However, the one position in the minors where they seem very deep right now is in the outfield. That could be an area they could subtract from to add elsewhere. I think the White Sox timed their rebuild very well with free agency. Last year's lackluster free-agent class was a great time to be on the sidelines. The next two winters will have much better talent available. The White Sox don't have much on the books and will be in a good financial position to make upgrades.

Q: After Eloy comes up in April who's the next guy in waiting and when does he come up? —  @franknacchio19

CG: With two open spots in the rotation, we could see a few prospects compete for starting jobs in spring training. Jordan Guerrero, Jordan Stephens and Spencer Adams are possibilities. All three of them finished the season at Charlotte and could be close to knocking on the door. The next big name after that would seemingly be Dylan Cease, who if he continues to pitch like he did this past season will probably be on the Michael Kopech timeline to the majors, and Kopech came up in August.

Q: If the rumors are true and the Diamondbacks dismantle their roster, which player on their roster makes sense for this White Sox team long term? —  @mr_zablocki

Q: Who would you hypothetically trade for Goldshmidt? — @DaRealScaletta​​​​​​​

CG: Looking at the Diamondbacks' roster, there aren't many natural fits with the White Sox rebuild. Where's the All-Star third baseman on a rebuilding team with a four-year, team-friendly contract? I like Zack Greinke, but he's going to be 35-years-old and has three years and $104 million left on his contract. A 27-year-old Robbie Ray would be solid, but he's under team control for only two more years. Paul Goldschmidt is an all-world first baseman with three Gold Gloves, but he's a free agent after next season. Depending on what the White Sox do with Jose Abreu, who also has one year left on his contract, maybe they go after Goldschmidt next offseason if they don't re-sign Abreu.

Q: Tell a Yolmer story. — @NJBooth20

CG: Yolmer was wearing this cool T-shirt in the clubhouse this past season. On the front, it said "play hard" with a photo of him making Mickey Mouse ears. On the back it said "have fun," and there's the photo of him pouring Gatorade all over himself. I asked him if I could have one of those T-shirts. He said, "50 dollars." I countered with, "How about 30?" With perfect comedic timing, Yolmer came back with, "Make it 10." He might not be the best bargainer in the world, but Yolmer Sanchez is definitely one of the funniest people around.

Q: Why did Nagy run the ball on 3rd and 4?? — @rypie182​​​​​​​

CG: Not sure.

Q: Can I leave a voicemail? Too drunk to tweet. — @HurriKayne26​​​​​​​

CG: Rough Bears game.

Q: Who will be the biggest surprise and/or the greatest improvement for next season's team? — @nicklicious33​​​​​​​

CG: Good question. If he's able to come back, I can think of one person in particular who would be quite an incredible surprise in 2019. That's Danny Farquhar. At home in California recovering from his near-death brain aneurysm, Farquhar is training with the hopes of pitching in the majors again, possibly as soon as 2019. I wouldn't put it past him. He's a special person who has been defying the odds since that horrific night in April. It would be great to see!

Thanks again for all of your questions. We'll do it again next week.

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