James Shields will forever be a player that haunts Chicago White Sox fans. Fair or not, Shields will forever be known on the South Side for being the guy that the White Sox traded away future superstar Fernando Tatis Jr. to acquire.
It's not even Shields' fault, although his 5.31 ERA in a White Sox uniform certainly doesn't help. This is just how it goes when you're involved in a franchise-altering trade.
James Shields being the figurehead of the 2016 White Sox collapse and the worst trade in franchise history has actually made a lot of fans forget about his other role in baseball infamy. Fortunately and hilariously, his old White Sox teammates still remember and never let him forget.
In one of his final starts with the San Diego Padres before being traded to Chicago, Shields gave up a home run to New York Mets starting pitcher Bartolo Colón. It was a moment that seemed impossible and took the baseball world by storm.
"THE IMPOSSIBLE HAS HAPPENED!"
— FOX Sports (@FOXSports) May 7, 2025
OTD in 2016, pitcher Bartolo Colon hit his first and only career home run at age 42 pic.twitter.com/ewfv9PPXyQ
The White Sox teased Shields
According to former White Sox third baseman Todd Frazier, it's a moment that would come up in the clubhouse from time-to-time.
"Me and Mike Pelfrey and Derek Holland were really close with him," Frazier told me in an interview a few weeks back. "When we were playing cards and we ended up beating him or he's beating us, we'd bring up some things. Knowing him, he was like 'Bro, really you're going to bring that up?!'"
The Baseball Insiders - Talking with former #WhiteSox third baseman Todd Frazier! @FlavaFraz21
— Sam Phalen (@Sam_Phalen) June 3, 2025
- The James Shields trade
- Hawk Harrelson leaves the booth to check on him
- Which former teammates are HOF worthy?
WATCH: https://t.co/zzCQi0WYx3 pic.twitter.com/nEqhmwpZ50
It was all in good fun between Frazier, Shields, and other White Sox teammates. Frazier referred to Shields as a "fun loving guy" that he always enjoys seeing.
Holland and Pelfrey both pitched for the White Sox for one season in 2017. It makes sense for that to be the year to take some jabs. There was way less pressure with the Sox starting a rebuild.
This is an example of what happens in a baseball clubhouse when the players have good chemistry. The 2016 White Sox often get a bad wrap for having clubhouse issues and tension between players, but in many ways, Frazier believes it was trade rumors that tore the Sox apart.
"You think it's motivation, but you don't know what everybody's thinking," Frazier said of the White Sox front office making a gutsy mid-season move to acquire Shields. "Next thing you know, they're talking about me ending up leaving, and you're like 'Why are we not just playing baseball? Put the best guys out there to play the game.' We're losing games left and right, fans are getting restless, the Cubs are doing better than the White Sox, and it just fell apart."
The White Sox started the 2016 season with a 23-10 record. They went 4-15 over their next 19 games, putting them in a desperate spot to find answers.
On June 4, the Sox traded Tatis to San Diego for James Shields. They played mediocre baseball with a 49-57 record the rest of the way.
Chicago traded Chris Sale and Adam Eaton in the ensuing offseason, sparking a massive rebuild. Frazier was traded to the New York Yankees in July of 2017.
Todd Frazier spoke with Southside Showdown on behalf of OFF! and their new Squish the Bug campaign, which ties into a Little League World Series sponsorship. Before Todd was a Home Run Derby champion, he was a LLWS hero for Toms River in 1998, of course.