Manny Machado is off to San Diego. The Chicago White Sox decided it wasn’t a smart idea to pay Manny Machado, one of the greatest free agents we will ever see, an appropriate amount. Instead of adding Manny Machado, they added all of Manny Machado’s friends. But not him.

First of all, this is a cowardly move from one of the most cowardly owners in sports. Jerry Reinsdorf’s biggest contract with the White Sox is still the six-year, $68 million contract given to Jose Abreu. Reinsdorf was too scared to pay Machado a guaranteed salary in seasons in which he will be 93 and 94 years old.

Jerry Reinsdorf is the epitome of an owner the fans are bred to hate. Reinsdorf had always been heralded as the Messiah in Chicago, but ever since Michael Jordan left the Bulls, he has one title to his name with the Sox in 2005. He’s never spent money. He’s never truly cared about building a winning team. His claim to fame not being Rocky Wirtz really fades off when Rocky Wirtz is no longer in the equation.

We were all wrong about Reinsdorf. I know I wasn’t the only one that thought Jerry would actually want his teams to win another title in his lifetime. However, with Gar Forman and John Paxson still running the show, it’s clear that wasn’t going to be the Bulls. But the White Sox looked good, or so we thought.

If the White Sox were truly unwilling to give Manny Machado what he wanted, they aren’t going to give their Plan B, Bryce Harper, what he wants. They aren’t going to give Nolan Arenado what he wants, given their insistence on Yoan Moncada playing 3B in the future. They aren’t going to be players for Mike Trout in two years because Trout’s contract is going be monstrously higher than both Machado’s and Harper’s, and Reinsdorf won’t be willing to pay that.

They’ve got a good farm system, but is it good enough? Their golden goose, Yoan Moncada, still has a lot of developing to go at the major league level. Their future ace is already on the shelf with Tommy John surgery. Promising outfielder Luis Basabe is already hurt. None of their “first wave” have actually had successful rookie seasons in the majors. That’s something none of the previous rebuilds, like the Astros and Cubs, have been able to say.

The Sox better hope Eloy Jimenez is actually what their fans think he is, because only one of their other big-name prospects, Nick Madrigal, has really lit it up at the plate so far down on the farm. Manny Machado was going to be the piece that made the whole thing go. He was the signal that the White Sox are truly back. But he’s not going to be there.

Manny Machado would have been bigger for the Sox than just adding a generational shortstop. They would have finally started to shed that “little brother” label they seem contempt to keeping. They would have set a precedent that winning, or at least going all out to win, was in the White Sox DNA. But Jerry Reinsdorf would rather hoard money ten years from now rather than try to actually win baseball games.

I guess we shouldn’t be surprised that the White Sox are baseball’s poster child for futility. They’ve been to the playoffs only nine times since 1906. 1906!!! The Cubs, who went 108 years without winning the World Series, have won 11 pennants since 1906. No wonder the Sox are the “little brother,” they make no intention to change that.

The bottom line is this: you can’t win without spending money. The Cubs got their ace pitcher and their World Series MVP by spending big. The Astros spent a lot, adding an ace to a roster full of veterans paid quite a bit. The Red Sox had the biggest payroll last year by a mile. Those three teams had success, yet Jerry Reinsdorf wants to replicate them without spending money?

I’m starting to think the White Sox aren’t going to be good again until Jerry Reinsdorf is no longer running the show. Every team needs to make that one big addition to supplement their rebuild, and the White Sox have failed to do so. Where does this leave them? Well, for the time being, purgatory.

Manny Machado was the key out. With Reinsdorf running the show, it seems as if they’ll need a Houdini-esque escape.

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