Spiegel: Why The Machado Miss Hurts So Much

Sad truths emerged as history repeated itself in some ways.

Matt Spiegel
February 20, 2019 - 4:42 pm

(670 The Score) It hurt White Sox fans like a knife to the ribs. I was surprised at how much it hurt them.

And the news itself shouldn't have. The story brewed for months, the White Sox evolving in that time to become the all-too-familiar organization known as The Chicago Leverage. The Padres dominated the rumor mill over the last three weeks, and star free agent Manny Machado choosing them over the White Sox on Tuesday should've felt more inevitable.

But it stung people, brutally. And over the next 24-36 hours, it has only gotten worse.

Sad truths have emerged.

The entire White Sox organization, including the owner, genuinely wanted to sign Machado. This wasn't some PR show to feel like a real big boy franchise with a seat at the table. They legitimately tried to get it done. Myriad staffers got involved in recruitment pitches. Family and friends were signed as if the White Sox were Kansas basketball hiring Ed Manning as an assistant coach so son Danny would attend. They wanted Machado. 

But in the end, the White Sox decided to draw their own specific line in the sand, and it killed them -- $300 million guaranteed wasn't going to happen. Their offer was for eight years and $250 million guaranteed with vesting options in the ninth and 10th years -- which are theoretical realities, not direct deposits showing up every two weeks like clockwork. And so Machado agreed to a 10-year, $300-million deal with the Padres.

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The difference between $250 million and $300 million isn't as big to the team as it is to the player. The player sees that extra $50 million guaranteed and feels the difference -- viscerally, easily. It’s an entirely understandable deal-clincher. The team is balking at money due in 2027 and 2028, when the landscape of the entire sport could have shifted and a title or two could have already been delivered. To offer an average annual value of $31.25 million dollars for eight years and then balk for two more years makes little sense.

For the White Sox, it’s an extremely shortsighted hard line to draw. Especially when you’ve known for the entire offseason that $300 million guaranteed is exactly what Machado wanted.

Side note: Executive vice president Kenny Williams needs to not be allowed to speak when news of this size breaks. His awkward muscling up has become so predictably off-putting. He delivers double talk that leaves a mess for general manager Rick Hahn to clean up. Williams brings anger mixed with disdain. He doesn't make fans feel better.

And what of the player opt-out after year five that Machado got in San Diego?  Was it in the White Sox's offer or not? They refuse to clarify explicitly. In a general sense, the report of the White Sox not believing in opt-outs as an organizational philosophy has since been aggressively fought by the team itself. Hahn already took to the radio and refuted it. Several media members received texts from White Sox brass specifically about that report, wanting us to know that it was wrong.

The White Sox did give Albert Belle an opt-out in his five-year contract he signed ahead of the 1997 season. But remembering he specifics of it, you realize it came with a big ole team-friendly caveat.

Belle’s then-record $55-million dollar deal had a unique clause calling for his pay to be consistently among the top three salaries in the game. If it wasn't, he had the right to opt out. After two seasons, that $11 million had dropped out of the top three, so Belle’s agent asked the White Sox for an overall raise of $4.25 million over the last three seasons. That amounted to 1.4 million annually. The White Sox refused, even though Belle had just hit 49 homers, and led the league with a 1.055 OPS and 172 OPS+. Belle elected to opt out of the deal as the clause allowed and went back into free agency. The Orioles gave him more than the rest of the White Sox contract called for over five sour seasons, so hey, good for Albert and the White Sox both. Belle faded and broke. The final three years of salary went to a man who didn't play.  

In January, there was a report from Andy Martino of SNY TV that the White Sox's contract offer to Machado had a potentially similar structure:

The sides have at least discussed a contract structure that would allow Chicago to exercise an option after year three that would trigger team control for an eighth or ninth year, according to major league sources. This probably accounts for some of the confusion over whether Machado has a seven- or eight-year offer on the table. He has likely been offered a contract that could be either.

In that structure, Machado would get to opt-out after 2021 if the team didn't opt in. The Yankees and reliever Zach Britton recently agreed to that structure, which Britton’s agent Scott Boras called a "swellopt" in an interview with Ken Rosenthal of the Athletic.

Maybe the lack of an opt-out didn’t matter to Machado. Maybe it was only about the simple $300 million guaranteed fully. But history says that if there were an opt-out even considered, the White Sox would 've wanted it to somehow be on their terms.

Machado chose a beautiful city in southern California in a market in which there should be little pressure to win and maybe even less to be a media-friendly role model. Despite the White Sox's legit courtship efforts, he turned them down. It stings to be passed over.  

Ultimately, this miss is a gut punch to the most ardent, because it’s hard to even call it progress. Yes, the White Sox were at the table. But the entrée never was served, for reasons all too familiar and within historical character -- ownership refused to go that extra financial mile. 

The restaurant will be open next winter as usual. The White Sox should make sure they come prepared to pay what the menu calls for.

Follow Matt Spiegel on Twitter @MattSpiegel670. For more from and about Matt, visit​​​