25 biggest disappointments in Cubs history that still sting Chicago fans today

Even growing up in the 1990s, the Chicago Cubs were the 'Lovable Losers'. Sure, they'd at least gotten back into the playoff picture a few times in the 80s and, as a little boy, Sammy Sosa's historic 1998 season captured my wildest imagination, but there was little to show in the way of results for my team.

Looking back over the Cubs' 150-year history, you could write a book (or several) on all the disappointment, heartbreak and gut-punch moments the team has delivered. But, here's a look at some of the biggest that recent generations may recall. And, don't worry, modern-day fans aren't spared pain here, either.

25 moments in Cubs history fans wish they could forget

25: Decades of futility: A nearly-40-year stretch with nothing to show

After losing the 1945 World Series to the Detroit Tigers, the Cubs embarked on a two-decade streak with zero playoff appearances to their name. The next time Chicago played postseason baseball came in 1984, when Ryne Sandberg captured NL MVP and Rick Sutcliffe dominated after coming over at the trade deadine. Unfortunately, the magic of that summer faded come fall... but more on that later.

24: The 2024 fade : Another disappointing finish

Craig Counsell was the missing piece. At least, that's the message fans got from Jed Hoyer when they fired David Ross in Nov. 2023. That message fell flat late the next summer, though, when the Cubs went 13-13 in the final month, falling just one game short of a playoff spot. Oh, and just to rub salt in the wound, Counsell led the team to the same 83-79 record Ross posted the year prior.

23: Trading Rafael Palmeiro: A future 500-homer bat is dealt to Texas

With Mark Grace on the rise, the Cubs traded Rafael Palmeiro (and the embodiment of longevity, Jamie Moyer, among others) to the Rangers in exchange for a package headlined by Mitch Williams. The lefty was an All-Star closer in 1989, which was the primary focus, but Palmeiro went on to smack more than 500 homers, establishing himself as a premier power threat for years to come.

22: Another October loss to the Marlins: An eerie 2020 Wild Card Series

The 2020 MLB postseason was a strange time. The world was still locked in the throes of the COVID-19 pandemic and the majority of the playoffs were played in empty stadiums with cardboard cutouts. At least nobody had to watch the Cubs get bounced by the Marlins at Wrigley Field in what wound up being the core's last playoff appearance, I guess?

21: The Corked Bat: Sammy Sosa's infamous 2003 ejection

A misused batting practice bat or something more? Sammy Sosa is best remembered for being the only player in MLB history to have three 60+ homer seasons to his name, but alongside PED allegations, his reputation took a hit when he was ejected after using a corked bat during a June 2003 game against the Tampa Bay Devil Rays. He played just one more year with the Cubs before getting traded to Baltimore following the 2004 season.

20: Corey Patterson goes down: Devastating injury sidelines young outfielder

Given how the 2003 campaign wound up playing out, losing Corey Patterson to an ACL + meniscus injury in early July remains one of the great 'what if' moments in recent decades for Cubs fans. Instead of finishing his breakout campaign, he was sidelined in October and, after a strong 2004, never came close to replicating his early-career success.

19: 2019 September swoon: Collapse ends the Joe Maddon era

I remember sitting at a local bar, watching the Cubs lose their eighth straight game in September, knowing a reckoning was at hand. Turns out, I was right. Joe Maddon was given the boot, David Ross replaced him and the beginning of the end was at hand for the group that changed Cubs history forever.

18: Mark Prior runs into Marcus Giles: Talk about a freak injury

It hurts knowing Mark Prior has multiple World Series rings - but none came with the Cubs. He's cemented himself as the Los Angeles Dodgers' pitching coach, but once upon a time, he was going to be a generational arm for the Cubs. In July 2003 (seriously, a lot happened that year), he knocked Marcus Giles out cold in an on-field collision, injuring his shoulder. That injury is widely viewed as the catalyst for all of Prior's future arm troubles that had him out of the league by 2007.

17: Billy Goat Curse: Legend comes to embody decades of disappointment

During the 1945 World Series, Billy Sianis brought his pet goat to the game (buying a ticket for it, even), but fan complaints about the animal's odor led to Cubs owner Philip K. Wrigley forcing Sianis and the goat to leave. Sianis fired back, saying, "The Cubs ain't gonna win no more. The Cubs will never win a World Series so long as the goat is not allowed in Wrigley Field." Chicago didn't play in aniother World Series for 71 years when, in 2016, they finally ended the 'curse'.

16: 2023 September collapse: Wild Card berth evaporates in final weeks

We didn't know it at the time, but change was at hand in the dugout for the 2023 Cubs. In early September, the David Ross-led team had playoff odds north of 92 percent. But a combination of poor bullpen work, shoddy defense and a streaky offense saw the team go into a tailspin. Chicago went 7-14 from Sept. 7 and wound up missing the postseason.

15: Dodgers end repeat hopes: Cubs run out of gas in 2017 NLCS

A World Series hangover in the early-going and a team running on fumes by the end. The Chicago Cubs made a historic third-straight League Championship Series, but it was pretty clear they were outmatched by the Los Angeles Dodgers, who avenged their NLCS loss the year prior by vanquishing Chicago four games to one.

14: Will Clark ends the dream: 1989 NLCS loss to San Francisco

Still fairly new to the whole 'being in the playoffs' thing, the 1989 Cubs clinched a division title for the first time since 1984 but were dispatched by the San Francisco Giants in the NLCS, highlighted by Will Clark's two-run, eighth-inning single off Mitch Williams in Game 5. (Really makes the Palmeiro trade look bad knowing that's how Williams' '89 season ended, doesn't it?)

13: 97 wins, three games, done: 2008 NLDS sweep by the Dodgers

In 2008, the Chicago Cubs looked like the real deal, a team ready to put away talks of goats and black cats for good. They cruised to the league's best record (and a franchise high-water mark dating back to 1945), only to get boat-raced by Manny Ramirez in the NLDS. The Cubs were swept and, just like that, disappointment once again reigned in Wrigleyville.

12: Core gets torn apart: Emotional 2021 trade deadline fire sale

Family pictures in front of the outfield ivy. Emotional fans lined up outside Wrigley Field. The end of an era. The 2021 trade deadline saw Jed Hoyer trade Anthony Rizzo, Kris Bryant and Javier Baez, among others, closing the book on the 2016 World Series champion team and beginning a rebuild at the corner of Clark and Addison.

11: Mr. Cub never gets to October: 19 seasons, zero playoff appearances

Ernie Banks will forever be Mr. Cub. His loyalty, perseverance and character continues to stand the test of time. More than 10,000 plate appearances. Over 2,500 games. Zero playoff appearances. Just thinking about the fact that he never experienced playoff baseball with the team he loved so much... man, it just rips your heart right out of your chest.

10: Kerry Wood's elbow: A lost 1999 season after Rookie of the Year campaign

After turning in what's widely considered the best pitched game in MLB history in his fifth career start the year prior (and going on to win NL Rookie of the Year honors), Kerry Wood tore his UCL in spring training the following year, costing him the entire 1999 season. He wasn't done with the Cubs and was a huge piece of the '03 rotation, but at the time, it felt like, as Cubs fans, we just couldn't have nice things.

9: The Lou Brock trade: Brock dealt to the Cardinals in 1964

Worst trade in baseball history? Yeah, probably. The Cubs traded Lou Brock to the rival Cardinals in 1964 and he rewarded them by leading St. Louis to a World Series title (and another a few years later). A future inductee into the MLB Hall of Fame, Brock collected over 3,000 hits in his storied career - and only about 10 percent of those came in a Cubs uniform.

8: Maddux walks away: Cubs let future Hall of Famer walk after 1992

The Lou Brock trade might be the worst trade in baseball history, but the Cubs' decision to let Cy Young Award winner Greg Maddux walk after his Cy Young 1992 season is right up there with worst decisions ever made by any front office. Accusations of low-ball offers and an eventual breaking off of talks drove him to Atlanta, where he won the Cy Young in each of the next three seasons en route to Cooperstown.

7: The Last World Series: 1945 World Series loss to Detroit

When Sianis slapped the 'Curse of the Billy Goat' on the Cubs, the team was up two games to one in the 1945 World Series. They went on to lose the series in seven games to the Detroit Tigers, setting up what would eventually become one of the longest championship droughts in North American sports.

6: 48 hours at Wrigley: 2018 Game 163 loss + Wild Card loss to Rockies

Unfortunately, I personally bore witness to this one. Not only was I there for Game 163 and the Wild Card Game loss to - of all teams - the Colorado Rockies, but I was there for Game 162 as well. And, well, really since this point, the Milwaukee Brewers have had the Cubs' number and the National League Central has run through our neighbors to the north.

5: Swept by the Mets: 2015 Cinderella story gets snuffed out

Fan reactions to the 2015 NLCS were wildly varied. I, for one, was just thrilled to be along for the ride after the Cubs made their improbable run to the brink of a World Series. We all hated Daniel Murphy for his October heroics, but it definitely left a bitter taste. We'd feel a lot worse about this one if Chicago hadn't finished the job the very next year.

4: Another September stumble: 2004 late-season collapse

After coming tantalizingly close to a World Series appearance the prior fall, expectations were high heading into 2004. They had a two-game lead for a playoff spot with eight games left, but lost six of their final eight and were left shellshocked, watching the postseason from their couches just like the rest of us.

3: 1969 meltdown: Cubs squander a commanding NL East advantage

Cubs history is littered with late-season meltdowns, but nothing rivals that of 1969. The team blew an eight-game division lead in August as the 'Miracle Mets' surged, winning 24 of their final 32 as the Cubs dropped 18 of their final 27. Oh, and we added another chapter to the Cubs' book of curses, with the introduction of the black cat. Good times.

2: Through Durham's legs: 1984 NLCS Game 5

In the early-going, it was all good for Leon Durham and the Cubs in Game 5 of the NLCS against the Padres. He homered and Chicago had an early edge. Then, a ball went through his legs late, allowing San Diego to rally and go on to win the series, again stopping Chicago just shy of the Fall Classic.

1: Five outs away: 2003 NLCS Game 6

This list had to end this way and you knew it when you started reading. You'll notice that I didn't label this the 'Steve Bartman Game' because if you want a scapegoat, go find Alex Gonzalez, who booted a critical ground ball that should have stopped the bleeding. Regardless of where you put the blame, Game 6 of the 2003 NLCS against the Marlins was the backbreaker of a lifetime and, even more than 20 years later, it's unbelievable the Cubs lost that game.

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