2018-19 offseason continues to haunt the Chicago White Sox

With the National League Championship Series about to get underway, the Philadelphia Phillies, led by Bryce Harper, are set to face off against the San Diego Padres, led by Manny Machado. That isn’t very fun for Chicago White Sox fans.

These players have more in common with each other than just leading their respective teams to the NLCS.

For one, they’re both two of the greatest players in the game. For another, they were teammates on Team USA’s 18 and under squad when they were kids. Another fact is that they were both pursued by the Chicago White Sox in free agency entering 2019.

So why bring this up now? Why open up the old wounds? For one thing, it’s relevant given that the two elite players are facing each other in the playoffs, something the White Sox failed to make with the roster they had this year. One of them will be playing in the World Series this year.

If it had gone the opposite way with both players badly underperforming and the White Sox playing well, everyone would be giving the front office so much credit, calling them geniuses for not wasting money on star players. Given how things turned out, it’s only fair to point out that the opposite happened.

Another thing that detractors will claim is that they didn’t want to play here which is provably false. Kenny Williams said of both Harper and Machado that they “wanted to be here” in an interview with the Chicago Sun Times.

Bryce Harper said he had a really good meeting with the White Sox early in the free agency. If the White Sox offered those players the money they were worth, they absolutely would have signed with Chicago. The White Sox simply chose not to get them and look at how that’s worked out.

The 2018-19 off-season continues to haunt the 2022 Chicago White Sox.

This all could have been the White Sox, or it would be if the Chicago White Sox had a merely competent front office and an owner who cared about winning. Unfortunately, they don’t have either of those things so they’re unsurprisingly stuck with a mediocre baseball team.

It’s incredibly amazing that this organization could not be smart enough to sign two 26-year-old players entering the middle of their prime and solve the right field and third base situation for the next 10 years.

It would have been so easy and with only a 96 million dollar payroll entering 2019, they could easily have afforded both players.

After the two players signed with other teams, Kenny Williams lamented in an interview:

"“Harper [was] well out of our range. With Machado, we extended ourselves as far as we could without jeopardizing what we’re going to need to do in the future.Our fans would have been much more disappointed in our inability to keep this next core together. We would have overextended ourselves had we gone to an uncomfortable level.”"

Kenny Williams claimed they couldn’t sign Machado because the fans would have been much more disappointed to keep this next core together.

This is hilarious in hindsight, not only because the core ended up not being that good, but it isn’t even true.

The White Sox let former first-round draft pick and 2021 all-star Carlos Rodon walk in free agency without so much as a qualifying offer because they were scared they’d have to pay him.

Jose Abreu (part of this core) may soon leave as well. This sounds more like they just don’t want to pay anyone, or at least anyone good.

Furthermore, if Harper is well out of thier range, why even bother meeting with him at all? Why waste everyone’s time making him a video presentation and sending Jim Thome to meet with him?

How are they this incompetent? Did they really think he’d accept the lowest of low offers? It was no secret both guys wanted 300 million plus.

If the White Sox weren’t willing to make him a real offer they should have spent the off-season pursuing more realistic free agents. It’s also not true that he was out of their range given their low payroll.

Instead, the Sox spent the offseason acquiring former San Diego Padres in Jon Jay and Yonder Alonso because they both knew Manny Machado. They thought that this would somehow make Machado sign with the Sox.

The former Padres instead likely told Machado to sign with San Diego instead, making them two of the most unlikeable figures in Chicago White Sox history.

Do you know who else knows Manny Machado? His former Team USA teammate Bryce Harper. Maybe they should have signed him instead.

This doesn’t even mention that the Padres rebuild was kick-started by the White Sox handing them Fernando Tatis Jr. and taking James Shields off their payroll. Maybe they never sign Machado without that happening.

Now here we are with the Manny Machado-signing Padres facing the Bryce Harper-signing Phillies in the League Championship Series, something the White Sox have failed to make since 2005 and haven’t reached the entirety of Rick Hahn’s tenure.

Maybe this would ignite some humility from Hahn and he can admit he was wrong to not sign the players but no. Instead, he brags about how much they’ve “accomplished” and says he was shocked with the team’s performance this year.

With the lack of star players on the roster, nothing about it was shocking. The fact of the matter is, if the best position player on your team is Tim Anderson, you’re not going to be winning a championship.

You might be able to squeak out a division title if you have an ace starting staff led by Carlos Rodon but the White Sox don’t even have that anymore.

The Chicago White Sox franchise was in desperate need of a superstar and they came across the best two chances they’ll ever get and they absolutely blew it. There will be no coming back from this.

This is what makes Hahn’s “seat at the table” comments so upsetting. This was a big opportunity as it doesn’t come around often and they completely blew it.

Even if the White Sox had only signed Machado, his 6.8 WAR this season would likely have put them in the playoffs which they only missed by 5 games. They also could have been more aggressive at the trade deadline before then. In the playoffs, anything’s possible.

Some detractors will point to the Cleveland Guardians as evidence that a team can win without spending money.

Yet, the Guardians still spent 150 million on Jose Ramirez which is more than double any contract given out by the White Sox.

There’s no way the Guardians would be as good as they are without superstar Ramirez who took a hometown discount and would have made a lot more on the open market.

The best thing the Sox could do to salvage their roster would be to give Machado’s 250 million dollar contract to Trea Turner or Carlos Correa (moving Anderson to 2B) as that would at least solve their infield problems. Yet Hahn isn’t even going to do that even though that’s probably what they should be doing.

Regardless, likely no free agent that hits the coming market will be as good as Harper or Machado, and free agents will only get more expensive as the years go on, putting them further and further out of the White Sox price range.

Do you think the Sox will spend 450 million on Shohei Ohtani or Juan Soto (who’s not as good as Bryce Harper/Manny Machado)? That’s a good laugh.

The fact is the White Sox could have easily afforded both future Hall of Fame players as their salaries will appear more moderate as inflation goes up.

Given the White Sox’s 196 million dollar payroll from last season, they could have given a combined 55 million to Harper and Machado, another 22 million for Carlos Rodon, and still have over 119 million dollars for the rest of the team!

Given how mediocre the rest of the team is, that shouldn’t have been a problem. The problem may be that the White Sox severely overrated their core, which really speaks to the arrogance of both Kenny Williams and Rick Hahn.

Despite all evidence to the contrary, they really think they are the smartest guys in the room and think they know so much better than everyone else.

Both of them should have been fired for their incompetence a long time ago, preferably during the White Sox reign of 7 consecutive losing seasons from 2013-19 which all happened with Hahn as the GM.

Unfortunately for Sox fans, Jerry Reinsdorf operates as if the game was the same as it was twenty years ago. Things won’t get better for Sox fans until a new ownership group comes along and fires Hahn and Williams.

That will be a great day to be a Chicago White Sox fan. Until then, we’ll have to settle for watching Bryce Harper or Manny Machado play in the World Series with an NL team and wonder what could’ve been.