As the Chicago White Sox rebuild continues, and a number of potential trades are making the rounds nine days before the non-waiver trade deadline, I take stock of where the team is and where it hopes to be in the future. And I’m not liking the look of things.

Critics will immediately say “the rebuild is right on schedule,” or “we have one of the top three farm systems in baseball” or “the team is flush with cash, we can sign superstar free agents!” Well, let’s start there and address each of these thoughts, then I’ll go further into why I am worried about the situation as a whole, and why the future scares me.

“The Rebuild Is Right On Schedule”

For now. The Pittsburgh Pirates began a rebuild in 1993 and it was right on schedule at one point. I remember it was a five-year plan, they were going to rebuild the farm system and have the team ready to contend in five years. Well, they never got that far because they trashed it and started over in 1996. And a new five year plan was put in place. Then a few years later it was trashed. This continued on for 20 years before the team actually started to compete again, and the Pirates became one of the laughingstocks of Major League Baseball.

Sometimes these things don’t go to plan. You might think you have it all laid out and some of the players you are most counting on fail to develop. Or get injured. Maybe they’re just not as good as they seemed. Maybe they’re AAAA players; they excel at AAA but fail at the MLB level, too good for the minor leagues but struggle at the Major League level.

I worry about this as I watch Tim Anderson (.241) and Yoan Moncada (.234), two of our better prospects and the “first wave” of youngsters to hold down full-time MLB positions, fail to reach a .250 batting average. On the pitching end, Lucas Giolito is struggling to a 6.18 ERA. These kids are supposed to be a major part of the rebuild, part of the foundation that we build a winner on. And I don’t think anyone expected them to struggle to this extreme.

So what happens when the foundation doesn’t stand? You have to scrap it and begin again, as the Pirates did 25 years ago. And how much rope do you give these kids?

“We Have One Of The Top Three Farm Systems In Baseball”

The White Sox rebuild began at the end of the 2016 season, when they traded Chris Sale to the Boston Red Sox for four prospects and Adam Eaton to the Washington Nationals for three pitching prospects. Of the seven players acquired, six have stuck and still have a bright future as far as their progress through the organization is concerned.

Then several months later, the White Sox traded Jose Quintana to the Chicago Cubs for four prospects. All four of whom are still in the organization and playing well.

Bottom line is, that’s ten players acquired in total, along with a number of players the White Sox have drafted in recent years who are considered top prospects, including catcher Zack Collins, first baseman Gavin Sheets, and this year’s top draft pick, Nick Madrigal.

White Sox general manager Rick Hahn has said himself that he expects the return on all these players to peak at about 25%, meaning only one out of four will develop into a star at the Major League level. So feasibly, this entire rebuild could produce four or five MLB regulars. Let’s suppose Eloy Jimenez, picked up in the Quintana deal is one of those, along with Moncada, Michael Kopech (acquired in the Sale deal), Reynaldo Lopez (acquired in the Eaton trade) and Dylan Cease, also picked up in the Quintana deal.

And let’s sweeten it a bit further and say Madrigal develops into a star, even though he is technically blocked at both positions he plays (at second base by Moncada and at shortstop by Anderson), its possible a position change for someone could result in all three having a spot in the lineup. And maybe a darkhorse develops somewhere in the minors and reaches stardom beyond what anyone had anticipated for him.

You’re still well short of a full Major League roster that’s ready to compete, but in that event we have thought number three, and that’s the one I dislike the most.

“The Team Is Flush With Cash, We Can Sign Superstar Free Agents”

Only twice in the history of this franchise has there been a free-agent signing of a legitimate “superstar.” The first was in 1981 when Carlton Fisk, a future Hall Of Fame catcher, signed after his contract from the Boston Red Sox was mailed to him late. The second was malcontent Albert Belle, who was signed to a five-year, $55 million contract that included an out that allowed him to void the deal if he was not among the top three highest-paid players in the league. Following year two, he did just that, and headed for Baltimore.

Top free agents have never signed with the White Sox. Never. The largest contract the team ever gave out was to Jose Abreu prior to the 2014 season, a six-year, $68 million deal, which he also opted out of and opted into arbitration. So not only have the White Sox never signed a player to a $100 million deal, they’ve never signed a player to a $70 million deal.

In fact, let’s look at the last White Sox rebuild, the 1997 “white flag trade” that ended the Sox short run as contenders in the mid-1990s but did set them up to win the 2000 American League Central title. That team featured a number of legitimate stars, none of whom was acquired as a free agent and certainly none who were paid like it. Paul Konerko (trade), Frank Thomas (draft), Carlos Lee (amateur free agent), Magglio Ordonez (amateur free agent), James Baldwin (draft), Jim Parque (draft) and Keith Foulke (acquired in the “white flag” trade).

In the early 1990s the New York Yankees were flush with cash, and free agents turned them down regularly, including Greg Maddux (who signed with the Atlanta Braves) and Barry Bonds (who signed with the San Francisco Giants), both of whom took less money than the Yankees were offering. Just because you make the biggest offer doesn’t mean players are going to sign, sometimes there are better offers but with less money.

Adding to this issue is the fact that two of the teams that have the most cash for free agent signings also have outstanding farm systems, the Yankees and the Los Angeles Dodgers. These teams have money to burn but also have a lot of really good minor league talent, on par with the White Sox and maybe, in the case of the Yankees, superior to the White Sox system. So all things being equal, is a superstar free agent more likely to take a $150 million deal from the Yankees, with their history, bottomless cash reserves, MLB talent and minor league talent or a $60 million deal from the White Sox with their lack of MLB talent and excellent minor league system? Mark my words, major free agents (Manny Machado, Clayton Kershaw, Bryce Harper, etc.) are not even giving the White Sox consideration. Not when the Dodgers or Yankees or Cubs or Phillies can offer them four times what the White Sox will offer.

The bottom line is, the White Sox are walking on a razors’ edge, they need to beat the percentages and have more of their prospects reach stardom than the average 25%. In addition to that, they need superstar free agents to look past the weather, the far-below-average coaching staff, the long history of losing and the fact that they can make more money elsewhere to sign with a team that may or may not develop minor league talent into Major League talent. I would hate to be the one assigned to make that sales pitch.

Having said all of that, I still love my team and certainly wish nothing but the best on the team, as well as for myself and my friends who are fans. We all want to win. But I have been a fan of this organization for 27 years and I have four division titles and one World Series win to show for it. To put that into perspective, in that same 27-year period, the New York Yankees have won 13 division titles (and six Wild Card births) and seven World Series titles.

It’s hard to be a White Sox fan and it’s hard to put a lot of faith in anything connected to this team just based on a lifetime of mediocrity and worse-than-mediocrity. The fact that we have one of the most lackluster coaching staffs in baseball makes it that much more difficult to get excited about the future. If this team were truly looking to field a winner, it would start at the top with an excellent field manager and a staff that would teach the youngsters the right way to play the game. We have none of that right now. And its a good place to start.

As I write this, the White Sox are 34-63, 29 games under .500 and 20 games out of first place (and five games out of last place). Some think it will just instantly click for the youngsters, all of the minor league prospects will develop, the team will sign a number of superstar free agents and win several World Series titles between 2020 and 2025.

Some of us would love to see that but common sense says otherwise.

Regardless, I still maintain my South Side Pride. Go Sox!