The worst trade in White Sox history is even worse than we thought

Until recently, former Chicago White Sox general manager Rick Hahn hasn’t been too outspoken about his failures on the South Side.

Hahn, who spent more than two decades with the White Sox organization, was relieved of his duties during the 100-loss 2023 season, just two years removed from a 93-win season and back-to-back playoff appearances.

While he brought a starved fanbase back to the postseason, Hahn’s tenure as GM will be remembered mostly for it’s shortcomings. The White Sox never truly reached the perennial contender status he hoped for.

On Sunday, Rick Hahn joined Matt Vasgersian on the MLB Network podcast and reflected on his years as White Sox GM. He also revealed some new information about his most infamous trade and somehow, it makes the deal look even worse.

White Sox trade Fernando Tatis Jr.

The aforementioned trade happened in June of 2016, when the White Sox acquired right-handed pitcher James Shields from the San Diego Padres in exchange for right-handed pitcher Erik Johnson and 17-year-old infielder Fernando Tatis Jr.

This trade, of course, went on to be a complete disaster for the White Sox, as Shields pitched to a 6.77 ERA for the rest of the 2016 season in Chicago. Things didn’t get much better for Shields afterwards either - he finished the 2017 season with a 5.23 ERA. 2018 turned out to be the final year of Shields' career, and although he was able to throw over 200 innings for the White Sox, he had a mediocre 4.53 ERA and led baseball with 16 losses. 

Not only was the James Shields experiment a failure, but Fernando Tatis Jr. quickly emerged as one of the biggest superstars in baseball for San Diego.

Tatis is a two-time All-Star, two-time Silver Slugger, Gold Glove Award winner, and former MVP finalist at just 26 years old. He led the National League with 42 home runs as a 22-year-old.

Needless to say, this was a bad trade, and Rick Hahn knows that as much as anyone else.

“It begins and ends with Tatis. What fool would trade him?” Hahn told Vasgersian when asked about the trade he wishes he could have a do-over on. “Here’s the thing about Tatis. Obviously, horrible trade. San Diego actually asked for Erik Johnson as well as another arm initially... we were reluctant to include two arms. The second arm never went on to actually appear.” 

Hahn went on to credit San Diego for identifying Tatis as a player they wanted while he was still in the Arizona Complex League. But he admitted that the Sox pushed back on the initial trade offer before settling on Tatis as the second piece.

The trade is even worse than we thought

It didn't seem like the Fernando Tatis Jr. trade, which still haunts White Sox fans, could get any worse. Somehow, it just did,

Although no name was provided, Hahn’s admission that Tatis wasn’t the original target for the Padres, and that the original target never even made it to the Major Leagues, is a jarring revelation.

Every MLB executive can look back on a trade and kick themselves for making the wrong decision, but very few can look back and wonder "what if" as much as Hahn can here.

Now, instead of just wondering what would’ve happened if they never made the Shields trade, Sox fans are left wondering what would’ve happened if they’d met the Padres original asking price. 

The team still would have gone into a full rebuild after failing down the stretch of 2016. They still would have had the assets to acquire their top prospects. Think about how different the "core" might have been if Yoán Moncada, Luis Robert Jr., Eloy Jimenez, and Dylan Cease were also paired with Fernando Tatis Jr...

While there are many reasons the White Sox rebuild failed, it’s natural to wonder how much different it would’ve been with a worldwide superstar like Fernando Tatis Jr. in tow.

How would having a talent like Tatis have impacted the organization's spending decisions, as well as their failed pursuit of other superstars? Would Jerry Reinsdorf have been more motivated to supplement the core with a player like Tatis aboard?

It’s also fair to question whether Tatis would even be the player he is had he remained in a White Sox organization that has had trouble developing position players.

There are many questions that we may never receive answers to. But the more details that emerge about the trials and tribulations of the era that was supposed to be the golden age of White Sox baseball, the more Sox fans will wonder how it was botched so badly.