The 2025 World Series gets underway Friday night between the Toronto Blue Jays and the Los Angeles Dodgers.

Only one former Chicago White Sox player will appear on either roster — veteran right-hander Chris Bassitt.

Bassitt’s role with Toronto has shifted in October. The emergence of young arms like Trey Yesavage and the breaks between games (allowing for smaller rotations) have pushed him to the bullpen, but he’s still found ways to contribute. His scoreless eighth inning in Game 7 of the ALCS was a massive reason the Blue Jays punched their ticket to the Fall Classic.

Seeing Bassitt pitch in a big postseason moment — and now on the sport’s biggest stage — brings back memories of his brief stint on the South Side. More specifically, it reopens the wound of a trade that deserves far more attention than it gets.

The Infamous White Sox-Padres Trade

White Sox fans (and the rest of the baseball world) often point to the James Shields–Fernando Tatís Jr. trade in 2016 as the poster child for the franchise’s missteps.

After a hot start that year, the Sox tried to salvage fading playoff hopes by acquiring Shields from the Padres. The move was supposed to stabilize the rotation. Instead, it cost them Tatís — then a lightly regarded prospect “thrown in” alongside pitcher Erik Johnson.

Tatís went on to become a three-time All-Star, two-time Silver Slugger, and Gold Glove and Platinum Glove winner. He’s hit more than 150 home runs and was an MVP finalist in 2021. Yes, his injuries and PED suspension have dulled the narrative a bit. But for a while, Tatís was the face of baseball — and every highlight he produced was a painful reminder of the undoubted worst trade in White Sox history.

Or at least, that’s what everyone thought.

A Trade That’s Somehow Worse

Lost in the conversation is another trade — one arguably even worse — made just a year earlier.

After finishing 73–89 in 2014, the White Sox did what the White Sox always seem to do: overreact. They tried to patch together a contender with a handful of free-agent splashes — Melky Cabrera on a three-year, $42 million deal and David Robertson on a four-year, $46 million contract.

They also made a trade that was supposed to put the pitching staff over the top. They traded for Jeff Samardzija from the Oakland Athletics — a deal meant to create a three-headed rotation with Chris Sale and José Quintana. Samardzija had just posted a 2.99 ERA over 219.2 innings between the Cubs and A’s. On paper, he looked like the perfect workhorse.

The cost? First-base prospect Rangel Ravelo, catcher Josh Phegley, shortstop Marcus Semien, and starting pitcher Chris Bassitt.

Samardzija’s lone year in Chicago was brutal. He led baseball in hits and earned runs allowed, finishing 11–13 with a 4.96 ERA. The White Sox spent just two days all season above .500 — May 7 and May 9, when they were 18–17 and 19–18 respectively — and were 18.5 games back by September.

They traded for a rental, never extended him, and watched him walk for $90 million from the Giants that winter.

What The White Sox Gave Up

Meanwhile, the return package they sent away turned into a goldmine elsewhere. Marcus Semien has gone on to collect three All-Star nods, two Silver Sluggers, a Gold Glove, and more than 250 home runs. He’s finished top-three in AL MVP voting as a finalist three times and earned a $175 million contract from the Texas Rangers.

Chris Bassitt has made more than 200 career starts since leaving the South Side, owning a 3.64 ERA with an All-Star appearance and a three-year, $63 million contract from Toronto. Even Josh Phegley carved out an eight-year career as a reliable backup catcher.

Comparing the Mistakes

By total Wins Above Replacement (WAR), the White Sox were outgained by 67.9 WAR in the deal — more than double the gap from the infamous Tatís trade.

For context: Samardzija produced just 0.3 WAR in Chicago, while Bassitt has been worth 17.7 WAR since the trade. Semien has piled up 48.1 WAR, and Phegley added another 2.4. The difference between the two sides sits at 67.9 WAR. The Shields–Tatís deal? “Only” 26.9.

So yes — the numbers say it all. The Bassitt/Semien-for-Samardzija swap was statistically a far worse deal than the Shields-for-Tatís one.

Pointing this out doesn’t erase the pain of losing Tatís — it just highlights how many times the White Sox have repeated the same mistake. A front office desperate for shortcuts, trading years of control and upside for a short-term “win-now” arm that never delivers. That's how the White Sox did business, largely because Jerry Reinsdorf wouldn't spend at the top of free agency, so trades became Chicago's only path to acquiring stars.

Now, as Chris Bassitt takes the mound in the World Series, it’s hard not to think about what could have been — and how much further the White Sox might be if they’d learned from their own history a decade ago.