Braden Montgomery's Walk Off Joins List of White Sox "Instant Classics"

As soon as Braden Montgomery's first MLB home run snuck over the wall in left field on Tuesday night, giving the Chicago White Sox a walk-off victory over the Atlanta Braves, I immediately felt as though it was an "instant classic" for the White Sox fans tuning in.

That game had everything. Home runs, errors, defensive web gems, a White Sox comeback, and five runners thrown out at home plate. For a regular season game, the stakes felt incredibly high, especially for the White Sox, who have been scuffling a bit recently and are going to be seriously tested by the schedule over the next month.

So for the game to end that way, with one of the organization's most highly touted prospects hitting a walk-off home run against the best team in baseball and one of the best closers in baseball, becoming just the second hitter in the last 50 years to hit a walk-off home run in extra innings of his MLB debut, with Bob Costas on the call in the broadcast booth...that's one you'll remember.

And it got me thinking: What other games are on par with this one? If we look back at the last decade of White Sox baseball, what qualifies as an instant classic? A "remember where you were" game, if you will.

Incredibly, the White Sox have two and maybe even three of those games this season alone. But if you look at the last decade, moments like we had on Tuesday night are few and far between.

The other game from the 2026 season that is inarguably on this list is Edgar Quero's walk-off home run in the rubber match of the Crosstown Classic.

It was the most anticipated White Sox-Cubs series in years, and the game itself had everything. A clutch hit from Miguel Vargas, a verbal altercation between Cubs outfielder Pete Crow-Armstrong and a White Sox fan in the outfield that went viral and commanded national attention for weeks, a go-ahead three-run home run by Tristan Peters that was the first home run of his MLB career, and then a huge answer from Michael Conforto, who hit a three-run home run of his own to tie the game.

Then came the unlikeliest of heroes. Edgar Quero delivered a pinch-hit, two-run home run in the bottom of the 10th inning to send White Sox fans home happy.

It felt like a statement win for the White Sox at the time and a game that gave them momentum moving forward, as well as a feeling of belonging. It's also worth noting that the Cubs haven't won a series since that day in May. But in terms of all-time games between the Cubs and White Sox, this one is right up there, and it's a game Sox fans will remember for a very long time.

Shockingly (or maybe not shocking at all), you have to go all the way back to 2021 for the next instant classic game on my list. It's ALDS Game 3 between the White Sox and Houston Astros, the first playoff game played on the South Side of Chicago since 2008.

The energy in the ballpark that evening was unmatched. There were five lead changes in four innings. Sox fans serenaded Houston's starting pitcher out of the ballgame after a promising rally, and Leury Garcia's go-ahead three-run home run capped off a White Sox comeback that momentarily had every Sox fan believing the team might just come back and win the series.

While the White Sox bowed out with a whimper in Game 4 and were swiftly eliminated from the postseason, that night in Chicago felt like a reward for White Sox fans who had suffered through the rebuild and more than a decade of frustrating baseball.

And when I think about the future for the White Sox, whether it's in 2026 or in the years to come, my desire for more playoff appearances stems from chasing that feeling I had while sitting in the ballpark during Game 3.

Also during the 2021 season, no regular season game has felt as high-stakes as the matchup between the White Sox and New York Yankees at the Field of Dreams.

There was novelty to it at the time. There was pageantry. And for White Sox fans, it was a big deal to have the national spotlight shining on the South Siders.

The White Sox had played so well throughout the 2021 season, but a win over the Yankees on a national stage would feel like a true coming-out party, an announcement that the White Sox had arrived as contenders to win the American League.

What started as an incredible evening with a 7-3 White Sox lead turned into a nightmare when the Yankees stormed back behind home runs from Aaron Judge and Giancarlo Stanton in the ninth inning.

That blown lead has the White Sox about to embarrass themselves in front of the entire baseball world, but it simply set the stage for one of the most iconic moments in franchise history as All-Star shortstop Tim Anderson launched one into the cornfields and made himself a White Sox legend.

Of all the people to hit a walk-off home run, Anderson was the best possible option. He was the face of that team and one of the faces of baseball at the time. His energy and swagger embodied everything the White Sox wanted to be about.

And for a fan base that had only felt frustration from baseball over the previous decade, Anderson's home run created an indescribable feeling. It was a poetic moment that showed off why baseball is truly the best.

The final game on my list, and the final game that belongs in this tier over the last decade of White Sox baseball, is another White Sox-Cubs matchup. It's the go-ahead home run from Eloy Jimenez in 2019 and the iconic "Thanks Cubs" call from Jason Benetti echoing across Chicago television sets.

In 2019, the White Sox weren't quite contenders yet, but waves of prospects were beginning to arrive at the MLB level, and there was a clear feeling in the air that the White Sox were on the rise.

The Cubs, on the other hand, made the NLCS in three consecutive seasons from 2015-17. They made the playoffs again in 2018 but were clearly on the back end of their contending window, clinging to hope that their World Series-winning core could make one more run at a championship.

Tensions between the crosstown rivals were high back then. The White Sox wanted to break out of the Cubs' shadow, and the Cubs wanted to reassert their dominance.

To make things even more interesting, the 2019 White Sox saw the MLB debuts of Eloy Jimenez and Dylan Cease, two highly rated prospects the White Sox had received from the Cubs in a blockbuster trade.

That game on June 18 was the first time Jimenez had faced the Cubs in his MLB career, and the White Sox were still hanging around .500 at the time with a 34-36 record. So with the White Sox looking to make a statement at Wrigley Field, this was a game White Sox fans badly wanted to win.

And you couldn't script it any better than having Jimenez be the hero.

His go-ahead two-run home run felt like a shift in the Chicago baseball dynamic, even if the White Sox's run as the better team in town was ultimately short-lived.

At the time, though, I remember feeling like Eloy Jimenez was on his way to becoming a perennial MVP candidate and one of the best hitters in baseball. And the fact that the White Sox had gotten him from the Cubs twisted the knife a bit more and made it that much sweeter.

Perhaps this game loses some of its luster in hindsight, but the fact that we still remember Benetti's call so vividly speaks to the instant-classic status it carries.

Of course, with my list here, there's a pretty direct correlation between the White Sox being competitive and the number of games that stand out in our memory.

We've already had two of them this year, and you could argue that Miguel Vargas' walk-off home run against the Tigers after Munetaka Murakami went down with an injury also belongs on the list.

I opted not to include it because I do believe the instant-classic label is pretty exclusive. It's something that will stand out 10 years from now and still bring back vivid memories for White Sox fans.

But with the way 2026 has played out thus far, I wouldn't be surprised if there are more of these games on the horizon.