It’s easy to see baseball as a video game. Look at all those good players out there just waiting to be snapped up. Why not go get all of them?

Of course, reality is a much different story, and price tags, player preferences and roster construction make, for example, the White Sox signing Gerrit Cole and Stephen Strasburg and Anthony Rendon rather ... let’s say difficult. But there are a lot of good names on this winter’s free-agent market, and the White Sox have several stated holes to fill — and perhaps some unstated ones they’d be willing to fill if given the opportunity.

Former general manager Jim Bowden ranked the top 35 free agents over at The Athletic and listed the White Sox among the “best fits” for a few of them, one being Jose Abreu, who has long seemed a near lock to return to the South Side. That strikes as curious, perhaps just another example of a national media member omitting the White Sox or perhaps an insight into how realistic it is that the White Sox are able to make a run at multiple targets of significance. Remember, though, that Bowden’s the guy who said the White Sox were the front runners for Bryce Harper during last year’s Winter Meetings. Maybe they were at the time, but it sure didn’t play out that way.

So considering it seems the White Sox probably should have appeared a tad more frequently on that list, let’s take a look at how the game’s top free agents would fit with the White Sox. I took the top 20 names on Bowden’s list and grouped them by fit.

Would be a fit with any team: Gerrit Cole, Stephen Strasburg

The two top pitchers on the free-agent market are two of the game’s best arms and were on display all October long. Cole’s elite postseason performances only increased what was already expected to be the biggest sum ever given to a free-agent pitcher. Strasburg, meanwhile, was the star of the World Series and was named the MVP of the Fall Classic for his own out-of-this-world work. Both guys are going to get paid a ridiculous amount of money.

Obviously, these pitchers would look fantastic at the top of the White Sox rotation — and all other 29 rotations in the game. The hurdles have been discussed. Cole supposedly prefers pitching on the West Coast after growing up minutes from Angel Stadium in Anaheim. Strasburg might be following the path of Clayton Kershaw, who opted out of his deal with the Los Angeles Dodgers last winter only to negotiate a new deal with his current team. And then there’s all that money they’re expected to get. But if we’re strictly talking about fit, there’s no doubt either Cole or Strasburg would fit nicely atop the White Sox rotation alongside their fellow All Star, Lucas Giolito.

Elite talent, so you make it work: Anthony Rendon

Bowden actually listed the White Sox as one of his “best fits” for Rendon, the top free-agent position player on the market. Not sure how good the fit is, to be honest, considering he plays third base and the White Sox already have a third baseman, their best all-around hitter in Yoan Moncada. But there’s no doubt that Rendon’s bat would be just what the White Sox need in the middle of their lineup. He’s quietly put up MVP-type production in recent seasons, including a career year en route to a World Series win: a .319/.412/.598 slash line to go along with 34 homers, 44 doubles, 126 RBIs and 117 runs scored.

While the White Sox have a third baseman in Moncada, the opportunity to add that kind of production to the middle of the lineup would be too good to pass up. We don’t really need to guess if the White Sox would try to do that, either, as they just did try to do it last year, pursuing Manny Machado with Tim Anderson already claiming the job at shortstop. Here’s Rick Hahn from his end-of-season press conference:

“The talent pool is a little different free agent-wise this offseason, but I'm not going to say we won't be creative in a couple elements, whether it's via trade or free agency. Our roster does have a little bit of flexibility in it and we hope in the coming years to have more flexibility built in in terms of different positions that guys can go out and play.”

Great fits, but: Madison Bumgarner, Nicholas Castellanos, Yasmani Grandal

Bumgarner, Castellanos and Grandal all have so much to like about them as potential White Sox additions. But they also have some attributes that might make the White Sox like other options better.

While Bumgarner is arguably the best pitcher in postseason history — a 2.11 ERA in 102.1 October innings and a jaw-dropping 0.25 ERA in 36 innings in the World Series — some folks are worried about the stress on his arm because of all those high-leverage pitches thrown with championships on the line. He’s just 30 years old, a fact that’s surprised plenty in conversations about his upcoming free agency. Bumgarner is coming off a 3.90 ERA in 2019, the highest of his career, and isn’t exactly mowing guys down like Cole and Strasburg. But he’s got three rings in hand and would seem like the perfect guy to be the Jon Lester for this White Sox rebuild. But will Bumgarner, a multi-time Silver Slugger with 19 career homers, want to give up batting in the National League?

Castellanos has hit incredibly well at Guaranteed Rate Field in recent seasons, with a stupid good .316/.381/.579 line there in 2018 bested in 2019, when he slashed .417/.462/.792. That last batch of numbers were part of an excellent 2019 season that only got more excellent after a midseason trade to the Cubs. The White Sox need a right fielder and a big bat, and he would seem to solve those two items. The knock on Castellanos, however, is his defense in right field, with Bowden even writing “he’ll need to sign with a team that has plus defenders at the other two spots.” That does not describe the White Sox. Eloy Jimenez remains a defensive work in progress in left field, and Luis Robert, while billed as a strong defender in center, will be getting his first taste of the big leagues in 2020. Is it enough to scare the White Sox away from Castellanos? Or could they even convince him to DH?

Finally, Grandal is expected to be a popular man as a free-agent catcher with a very good bat and a reputation as a good pitch-framer. The White Sox, though, did not include catcher on their offseason to-do list with James McCann coming off an All-Star season and Zack Collins figuring to get a chance to do something at the big league level in 2020. While Grandal would figure to be an upgrade and more of a long-term solution — especially in light of McCann’s significant statistical dip after the All-Star break — are the other, stated items on the team’s offseason to-do list of greater import? Is upgrading at an already-filled position doable when the White Sox need new starters in right field, at DH and in the rotation?

The White Sox need pitching: Dallas Keuchel, Zack Wheeler, Hyun-Jin Ryu, Jake Odorizzi

The White Sox need starting pitching. Hahn has said the team will be shopping for it this winter, and there are a lot of options out there. But while plenty of focus has been on the Coles, Strasburgs and Bumgarners of the world, what if the White Sox try to fill in behind Giolito rather than in front of him or alongside him at the top of the rotation? Any of the five names above would not be the kind of dominant arm that would vault the White Sox from rebuilding mode to contending mode all by themselves, and adding them would show the team’s faith that Giolito and perhaps Dylan Cease and Michael Kopech, too, could carry the burden of being top-of-the-rotation pitchers for a perennial contender.

That’s not to say that these guys wouldn’t be good additions, they would just fit a little differently. Keuchel has a World Series ring and experience of being with a team that went from rebuilding to a championship. Wheeler is just 29 and has a lot of long-term promise after turning in sub-4.00 ERAs with the New York Mets in each of the last two seasons. Ryu led baseball with a 2.32 ERA in 2019 and put up a 2.71 ERA over the last three seasons with the Dodgers. Odorizzi, also 29, was an All Star in 2019 and could be a nice long-term addition.

There’s a hole in right field: Marcell Ozuna, Yasiel Puig

The White Sox need a right fielder. And while Castellanos might be the best free-agent option at the position, Ozuna and Puig aren’t too far behind. The White Sox have already been reported as interested in Ozuna, who had a .262/.327/.451 line with 52 homers and 177 RBIs in two seasons with the St. Louis Cardinals. He also hasn’t played much right field. There have been positive and negative results from Puig’s energetic on-field displays. He was more productive following his midseason trade to the Cleveland Indians but hasn’t been as productive as Castellanos or Ozuna. His .785 OPS in 2019 was the third-lowest of his big league career.

Those guys would be fits in that the White Sox need someone to play right field. They would be upgrades from the dismal production the team got out of that spot in 2019. But do either scream “slam-dunk long-term solution”?

Can he DH: Josh Donaldson, Mike Moustakas

Donaldson and Moustakas are two big bats that would look great inserted into the middle of the White Sox lineup. But neither is a DH by trade, causing some potential fit issues. Donaldson plays third, and while he’s good there, he’s not the kind of build-your-team-around-him guy Rendon seems to be. Would he be worth blowing up the infield alignment? And while Moustakas provides lefty power — something Hahn said the White Sox would like to add in an ideal world — he also plays on the infield with just 35 career games as a DH. Forcing a non-DH into the DH hole hasn’t always gone so well for the White Sox. See Yonder Alonso last season.

All that said, these guys swing great sticks, something the White Sox certainly could use more of. Moustakas has hit 101 homers in the last three seasons, including 35 in 2019 with the Milwaukee Brewers. Donaldson had 37 homers in his lucrative one-year deal with the Atlanta Braves. That’s the kind of pop the White Sox could need, so perhaps the hurdles to perfect-fit status would be worth it.

Do you pay for bullpen help: Will Smith, Will Harris

The relief market is thin on potential closers this season, which isn’t a bad thing for the White Sox, as they have a closer in Alex Colome and a setup man in Aaron Bummer. But the back end of any bullpen can always use fortifying, and Hahn & Co. could be faced with a decision over whether or not to use some of their much discussed financial flexibility to add a reliever of consequence this winter.

Smith and Harris were the two relief arms included in Bowden’s top 20, and deservedly so after their strong 2019 campaigns. Daniel Hudson, the former White Sox pitcher who moonlighted as the Nationals’ closer during a significant portion of the postseason, is also available.

Depends on how the rest of the offseason goes: Edwin Encarnacion, Cole Hamels

Hahn has never been shy about talking about his decisions as ones focusing on the long-term success of this rebuilding project. The need for every piece to be a long-term one will diminish if the White Sox get closer to contending for a championship, but right now, it still seems that a long-term focus makes the most sense. Many of the names discussed above fit that long-term category. Encarnacion and Hamels are not two of them. And so their prospective fit depends very much on who else the White Sox are able to add this offseason.

If they get some huge long-term pieces like the guys at the top of this list, guys who can boost their 2020 fortunes enough to get them into the contention phase right out of spring training, then Encarnacion and Hamels make sense as short-term adds who could be very beneficial in a 2020 pennant chase. But if the White Sox look like they’re going to break camp as more of a fringe contender, then perhaps older free agents like this don’t make as much as sense, as they wouldn’t be able to help the White Sox past the 2020 season.

Likely not on White Sox radar: Didi Gregorius

With Rendon, there’s a strong case to make about rearranging the infield if the opportunity to add him presents itself. But while Gregorius is a terrific defender and swings a strong bat, too, he’s not exactly the MVP-type talent that Rendon is. Anderson just won a batting title and seems like he’s pretty well entrenched as a White Sox cornerstone for the future. It’s one thing to potentially move Anderson to bring in someone like Machado. It’s another thing to consider moving him for Gregorius.

Welcome back: Jose Abreu

“If the White Sox don’t sign me, I’m going to sign here anyway. I’m going to sign myself here. I’m going to be here, believe me. I’m going to be here.

“I don’t want to miss this, I don’t want to miss what is coming, and I’m going to be here.”

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