The Sox managed to avoid getting swept north of the border Wednesday night with a 4-3 win over the Blue Jays. The previous two games were dominated by Josh Donaldson and D-Bo’s whistle saga. Gamesmanship aside, Donaldson made his presence felt in the first two games of the series, hitting two home runs with four RBI’s.

Donaldson’s big series suddenly caused an uptick in chatter about the possibility of the White Sox looking to sign him this upcoming offseason to play third base.

While Bryce Harper and Manny Machado are already the darlings of next winter’s free agent ball, with more talk about a pursuit of Machado here on the South Side. Many are now looking at Donaldson as a cheaper and more realistic target for the Sox to pursue.

This post will present a lot more questions than answers. Frankly at this moment there are so many moving parts that it’s basically impossible to clearly see or articulate what may go down this winter and beyond. The best I can do here is raise some questions and lay out some scenarios to chew on for the next few months.

As I mentioned above, Harper and Machado are the two crown jewels of what will be a loaded free agent market this offseason. Given the incredibly low payroll that the White Sox are going to have, it is my official stance that they need to make a serious and hard push for Harper or Machado, regardless of what people say about their chances.

You want to put the White Sox on the map? Open the checkbook and make those two guys say no to you. Period.

If rejection happens, then it’s time to possibly move on to secondary options. Enter Josh Donaldson.

The 32-year-old has hit 33, 37 and 41 homers in the last three seasons. He has 460 hits since arriving in Toronto before the 2015 season. On the outside all of the numbers look solid. He would add another power bat into a White Sox line-up that is suddenly blossoming with offensive firepower.

The main issue for me is that, much like Mike Moustakas this offseason, Donaldson isn’t getting any younger, or any better. His numbers, while good, have naturally been in a steady decline the last few years. We’ve seen how teams are venturing away from these long, expensive contracts for aging stars.

With somebody like Nolan Arenado looming after 2019, there’s no reason why the White Sox should throw a ton of money at an aging Josh Donaldson. The only way I see this working is if the White Sox keep the deal short as a bridge at third base until Jake Burger is ready, and whether or not the Sox believe in Burger at third yet is an entirely different conversation.

Burger’s achilles injury has sidelined him for the entire 2018 season, pushing back his development and timetable. The earliest we could expect to see him in Chicago is now probably… late 2020 or to start the 2021 season? I’m not sure the Sox are willing to wait that long to have a stable solution at third.

But that ties into another question, what is Yolmer Sanchez’s role in all of this? As we said this offseason, he’s affordable and can contribute offensively, defensively and in the clubhouse. But as this team improves all around, does he begin to slide into just being a utility infielder? His long term role is yet to be determined.

So a whole lot of this hinges on what the White Sox believe they’re going to get out of Jake Burger as a third baseman. We know what he can do offensively, but all of the question marks are about his fielding. If you listen to his interview on Barstool’s Red Line Radio, Burger comes off as a guy who is grinding to get better every single day, despite the injury. He carries the attitude that you look for in a big league ballplayer. The guy seems to have it all going on inside. The question is where does he fit in the Sox long-term vision for third base. A lot of these dominoes potentially start to fall once that is figured out.

But back to the belle of the third base “ball,” Manny Machado. Of course he’s been the main free agency desire for many Sox fans since this rebuild began to gain momentum. He is an all world talent, and set to make one of the biggest contracts in baseball history.

The insane money he is going to demand is an obvious hiccup, so let’s just leave that factor to the side right now. One new roadblock to this dream is that Machado moved to shortstop for the Orioles at the beginning of this season. So one can presume that wherever he goes in free agency he is going to want, and probably demand, to play shortstop.

Oh, wait, the White Sox already have a pretty dang good shortstop. His name is Tim Anderson.

While Timmy is obviously no Manny Machado, you’re telling me that the Sox would be willing to move on from a known commodity, a core piece like Tim Anderson so quickly? I don’t think so, and I also don’t believe they would shove Anderson over to third or somewhere else on the diamond just to accommodate Machado. The shortstop factor doesn’t de-rail this entire idea, but it definitely complicates it.

Would Anderson possibly volunteer a move to get Machado to Chicago? Who knows. Possibly? But I get this feeling that he really enjoys, and has a lot to offer, playing shortstop. Especially as he keeps building a rapport with fellow middle-infielder Yoan Moncada (The new Jordan and Pippen, baby).

All of that said, there’s no guarantee that Machado (or Bryce Harper) will even give the White Sox the time of day once free agency rolls around. They’ll have money to offer, but it’s yet to be seen if ownership will finally write that check that actually brings a superstar free agent to the south side.

So my take on all of it is this – figure out what you have in Jake Burger (obviously difficult since he’s missing all of this season), if you decide he’s definitely your future at third, great, maybe sign Donaldson to a short deal or stick with Yolmer to bridge that gap. If that’s not the case, give Machado a serious offer and make him tell you no this winter. If he does and Burger isn’t going to work, then I say wait another year and go after Nolan Arenado in 2019.

The Sox future at third has many moving parts. Much of it will become clearer as we move forward through free agency and Jake Burger’s development.

There are many routes that the Sox could take, they just have to make sure it’s the right one… at the right time.