With the Cubs returning to the postseason in 2025, here’s a look back at their biggest October blasts since the dawn of the new millennium.
Although the 2025 Chicago Cubs season has come and gone with a disappointing loss to the Milwaukee Brewers in the NLDS, the North Siders’ return to the postseason included a series victory in the NL Wild Card Round before overcoming a 2-0 NLDS deficit to tie the matchup before ultimately losing.
The Cubs’ four postseason victories brought fans on Chicago’s North Side a reason to celebrate October baseball for the first time since 2017, the last time the Cubs had won a playoff game or series up until this season.
While the Cubs have been around for nearly 150 years, it’s no secret that many of the franchise’s biggest moments have happened in the 21st century. Highlighted by breaking a 108-year championship drought in 2016, the Cubs also delivered significant playoff runs in 2003, 2015 and 2017, while making additional postseason appearances in 2007, 2008, 2018 and 2020.
With the World Series underway, myself and likely many other Cubs fans are reminiscing on their 2016 championship run along with the biggest playoff moments for the Lovable Losers in recent years.
Though there is little doubt that the biggest moments came in 2016, here’s a look at what I believe to be the 10 biggest Cubs playoff home runs of the 21st century.
10. 2016 NLDS Game 3: Kris Bryant two-run shot off Sergio Romo, 9th inning
After winning the first two games of the NLDS against the San Francisco Giants at Wrigley Field, the series shifted to then-AT&T Park as the Cubs looked to complete a sweep and move on to their second-straight NLCS.
Though the Cubs held a 3-2 lead in the eighth inning and looked to be in decent position to finish off the series, a three-run Giants rally gave San Francisco a 5-3 lead heading into the ninth, seemingly dashing the Cubs’ hope for a sweep.
After a Dexter Fowler leadoff walk, the 2016 NL MVP rocketed a two-run shot into the left field stands, tying the game at 5 and rejuvenating hope for the Cubs.
Although the Giants ultimately won Game 3 in the 13th inning, Bryant’s game-tying home run was a thrilling moment that solidified the club’s persistence and no-quit mantra that drove them to a championship later the same year.
9. 2003 NLCS Game 1: Sammy Sosa two-run shot off Ugueth Urbina, 9th inning
In a wild NLCS Game 1 that saw the Cubs squander a 4-0 lead in the first inning, the North Siders were left with one last chance to tie the game in the ninth inning, staring down an 8-6 deficit and a 1-0 hole in the best-of-seven championship series.
With two outs in the inning and facing Florida Marlins closer Ugueth Urbina, Cubs icon Sammy Sosa demolished a 1-1 slider, sending the ball onto Waveland Avenue and tying the game for the Cubs while they were down to their last out.
Though it’s no secret that the Cubs went on to lose this game in an 11th-inning heartbreaker en route to falling short in the series in seven games, there’s no overstating how massive this moment was for the Cubs and their fans.
It had been 95 years – this was one of those moments where it simply felt like destiny, even if it wasn’t anything close. Today, that matters little to Cubs fans – this moment remains legendary.
8. 2015 NLDS Game 2: Jorge Soler two-run shot off Jaime García, 2nd inning
It feels weird to assign this level of significance to a second-inning two-run shot, but it’s certainly crystal clear that this blast served as a massive turning point in this Cubs-Cardinals series.
After getting shut out 4-0 in Game 1 of the series in St. Louis, the Cubs fell behind early in Game 2 by virtue of a Matt Carpenter leadoff home run, leaving fans on the North Side grumbling at the possibility of a sweep at the hands of their archrivals.
The Cubs had an immediate answer, however, and managed to score three runs in the second inning with the ball only leaving the infield once. With a runner on first base and two outs, the Cubs looked to likely hold a solid two-run lead into the next frame – until Jorge Soler had something else to say about it.
The majestic blast doubled the Cubs lead, giving them all they needed for what would ultimately be a 6-3 win to even up the series. The home run also proved to be a turning point in the series as a whole, with the Cubs taking care of business at Wrigley Field to defeat the 100-win Cardinals in four games, their first NLDS victory since 2003.
7. 2003 NLCS Game 7: Kerry Wood two-run shot off Mark Redman, 2nd inning
Another moment that made it all feel like destiny when it ultimately wasn’t, Cubs fans still look back and rightfully treasure pitcher Kerry Wood’s majestic Game 7 home run that injected a true sense of hope into the Friendly Confines.
After a Miguel Cabrera three-run shot in the first inning put the Marlins up 3-0, Wood found himself at the plate with two outs and a runner on base in the second inning after catcher Damian Miller converted on an RBI groundout.
Locked in a full count battle, Wood rocketed the seventh pitch of the at-bat deep into the night, sending Wrigley Field into an absolute frenzy as he tied the game.
Though Wood ultimately surrendered seven earned runs in a heartbreaking 9-6 Game 7 defeat, his home run is still remembered as one of the last gasps of hope from an incredible 2003 season that fell short in the most painful of ways.
6. 2015 NLDS Game 4: Javier Báez three-run shot off John Lackey, 2nd inning
Another second-inning blast, this will forever be a legendary moment that felt like the true beginning of postseason greatness from the young core the Cubs had at the time.
Ahead 2-1 against the Cardinals in the best-of-five NLDS, St. Louis took a 2-0 lead in the first inning thanks to a Stephen Piscotty home run just four pitches into the game, putting the Cubs in an early hole. After getting a rally together in the bottom of the second inning, starting pitcher Jason Hammel miraculously belted a two-out RBI single to cut the St. Louis lead in half and keep the inning alive.
Shortstop Javier Báez, who was starting in place for the injured Addison Russell, was up next and showed no hesitation with what he was trying to do. Dealt a fastball touching the outside corner on his first pitch, Báez smacked it to deep right field, putting Wrigley Field up for grabs with a monstrous three-run home run that gave the Cubs a 4-2 lead.
Another moment that made it all feel possible, the broadcast booth left in absolute amazement in the wake of the home run perfectly summarizes what fans were feeling – excitement, jubilation, but above all else, true awe.
5. 2016 NLDS Game 1: Javier Báez solo shot off Johnny Cueto, 8th inning
A year after that famous Báez home run against the Cardinals, Cubs fans were treated with another one as they entered the playoffs with 103 wins and the best record in all of baseball.
Game 1 of the NLDS against the Giants quickly turned into a vintage pitcher’s duel, with aces Jon Lester and Johnny Cueto matching each other every step of the way as both teams were locked in a scoreless tie.
With both starters locked in beyond belief, Báez made his way to the plate with the bases empty and one out in the eighth inning, contending with the wind howling in towards the plate, dampening any potential power all night.
Undeterred, Báez clobbered every bit of a 3-2 offering from Cueto, rocketing the ball into left field as it barely made its way into Wrigley Field’s basket, narrowly winning its battle with the wind as it gave the Cubs all they needed with a 1-0 lead.
I was lucky enough to be in attendance at this game, and words can’t properly do the abrupt mood swing of Wrigley Field justice after Báez’s titanic shot. Aroldis Chapman ultimately slammed the door in the ninth inning, locking up a 1-0 Game 1 win for the Cubs.
4. 2016 World Series Game 7: Dexter Fowler solo shot off Corey Kluber, 1st inning
There will never be another game in North American professional sports that can even rival the intensity and stakes that Game 7 of the 2016 World Series offered, which made Fowler’s leadoff shot seem all the more gigantic and improbable.
Always known as a speedster with plenty of pop, Fowler had previously hit four playoff home runs as a Cub over the course of 2015 and 2016, though I don’t think anyone predicted this kind of start to what may be the greatest baseball game ever played.
With tensions at unforeseen levels for Cubs fans and truly the entire city of Chicago, Fowler launched a 2-1 offering from Cleveland’s ace that just made it over the center field wall, giving the Cubs an early 1-0 lead in the biggest roller coaster of a sporting event we will ever see.
Fowler’s home run was the first of very many highs and lows both fanbases were subject to during Game 7, but it was also a moment of sheer joy for Cubs fans – they had arrived on baseball’s biggest stage and they made it immediately clear they weren’t folding over.
The Cubs ultimately won this classic of a game by a score of 8-7 in 10 innings, securing their third title in franchise history and their first since 1908.
3. 2016 World Series Game 5: Kris Bryant solo shot off Trevor Bauer, 4th inning
I grappled with where to place this home run quite a bit, and initially had it ranked first, as it served as the true turning point that sparked a 3-1 series comeback in the World Series.
After splitting the first two games in Cleveland, the Cubs dropped both Games 3 and 4 at Wrigley Field, putting them on the brink of elimination for their final home game of the season in Game 5.
A battle between Jon Lester and Trevor Bauer, the latter of whom was on short rest, it was the then-Indians who struck first thanks to a solo shot from José Ramírez, taking the air out of the ballpark as Cleveland was on top 1-0.
The Cubs had the heart of their order up in the fourth inning, feeling the urgency to score as star reliever Andrew Miller, who had stymied the Cubs and all opponents all year, was waiting in the wings.
In what was perhaps their last chance to get to a Cleveland starter, Kris Bryant launched a leadoff home run on a 1-1 offering, tying the game for the Cubs and sparking a much-needed rally.
The home run was immediately followed by an Anthony Rizzo double, leading to the Cubs getting two more runs that inning from an Addison Russell RBI single and David Ross sac fly. Chicago went on to win Game 5 by a score of 3-2, sending the series back to Cleveland where they would complete the historic comeback.
2. 2016 World Series Game 6: Addison Russell grand slam off Dan Otero, 3rd inning
Facing elimination once again in Cleveland for Game 6, the Cubs made some early noise with a three-run first inning rally to build an early lead, and appeared to be looking for more in the third inning.
Taking on Cleveland starter Josh Tomlin on short rest, the Cubs loaded the bases with just one out in the third inning, prompting manager Terry Francona to go to his bullpen in an effort to avert a game-breaking inning.
Righty reliever Dan Otero entered the game for Tomlin, who mistakenly left Cubs shortstop Addison Russell a 2-0 offering right over the plate that he didn’t miss a single bit of.
The monstrous shot gave the Cubs a 7-0 lead that seemed to have every fan at Progressive Field thinking about a Game 7, paving the way for what was ultimately a 9-3 Cubs win to tie the series up at three games apiece.
1. 2016 NLCS Game 1: Miguel Montero grand slam off Joe Blanton, 8th inning
Ranking these top three home runs was extremely difficult, and it felt a bit weird to say that a home run in the first game of the NLCS was bigger than any in that year’s World Series – but I’m at least here to make the argument.
Facing the Los Angeles Dodgers, Game 1 quickly turned into a nailbiter after the Cubs had built an early 3-0 lead and were in control for most of the game. While L.A. got a run back in the fifth inning, it was a two-out, two-run single from SoCal baseball mainstay Adrián González that tied the game up at 3 in the eighth inning, turning a joyous atmosphere into an exasperated and anxious crowd.
To further rub salt in the wound, González’s big hit came off of star closer Aroldis Chapman, who would either have to be taken out of the game or work a second inning to keep the Cubs tied or close in the ninth inning. None of that ended up mattering.
With the Cubs putting runners on first and second base with two outs, Dodgers manager Dave Roberts elected to intentionally walk outfielder Chris Coghlan, bringing Chapman’s spot in the lineup up at the plate and forcing Cubs skipper Joe Maddon to either have Chapman take the plate appearance or pinch hit to remove him from the game.
Maddon tapped catcher Miguel Montero to pinch hit for Chapman, who quickly went down 0-2 on two sliders from Blanton. Having already seen two of the same pitch with the game on the line, Montero decided to sit on a slider and hope for the best.
Enter – the best:
Blanton erroneously threw Montero a carbon-copy slider on 0-2, which the catcher absolutely demolished to give the Cubs a 7-3 lead to ultimately lock up a 1-0 lead in the series.
Though the home run felt massive at the time, it felt even more significant in the days that followed. The Cubs went on to get shut out in both Games 2 and 3 of this series, falling behind 2-1 while having to play Games 4 and 5 in Los Angeles. While the Cubs bounced back to win three straight in the series for a 4-2 series victory, a Cubs loss in Game 1 could have put the team in an inescapable 3-0 hole with all else equal, almost certainly eliminating the possibility of the Cubs winning it all in 2016.
Montero had just two hits for the Cubs in the 2016 postseason, but one could easily argue they were the two biggest hits of the playoffs. After his Game 1 grand slam, Montero slapped an RBI single in the 10th inning of Game 7 of the World Series to give the Cubs an 8-6 lead, ultimately proving to be the game and series-winning hit with an 8-7 final score in that contest.
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