The 25 biggest Cubs killers who haunted Chicago throughout history

In every hero's story, there is almost always a villain. If your heroes on the diamond are the Chicago Cubs and players like Ernie Banks, Sammy Sosa, and Pete Crow-Armstrong, you know many villains who have terrorized the Friendly Confines over the years. The franchise that plays on the corner of Clark and Addison has been around for 150 years as of 2026 and has faced so many great athletes in that time, from division rivals or otherwise, that it's almost hard to remember them all.

Yet, there are still big bads. True Cubs killers who stand unrivaled as titans of terror, ruined games, and haunted the North Siders and their fans even after their playing days were over. It's easy to dread seeing them, yet, deep inside, it's undeniable that they make this game interesting and create demons to be slain en route to greatness. They are an inevitable, necessary evil, and they deserve some begrudging respect.

Finding the most fearsome isn't easy. Some inflicted career-long damage, while others brought maximum pain at the worst possible moments. Sometimes, the very best killers are not Hall of Famers, but good-to-great ballplayers who uniquely crush the Cubs. This ranking, inspired by stats, emotions, opinion, and stories from the game, is meant to be a reflection of a variety of players who caused heartburn in their own special ways.

25. Ozzie Albies

While this list consists mostly of older players who've inflicted entire careers' worth of pain on the Cubs, Atlanta Braves second baseman Ozzie Albies has earned a spot for how uniquely terrifying he's been to Chicago in a relatively short time. In 217 plate appearances across 49 games since his 2017 debut, he's slashed an eye-popping .357/.412/.638 with 12 home runs. At just 29 years old, this sample has a big ol' incomplete next to it, too. Perhaps I'm experiencing recency bias, but he feels like he's on pace for Cubs-killer greatness with how many agonizing moments he's already authored.

Albies has been one of the league's premier second basemen for nearly a decade now. He's already accrued 23 fWAR across parts of ten seasons, has four All-Star nods to his name, two Silver Sluggers, and a World Series ring. A .262/.316/.446/108 wRC+ slash line is good, but those numbers are worlds apart from what he's done against the Northsiders. 2023 stands out among his many back-breaking hits, when his walk-off single after Ronald Acuna Jr's 40-70 celebration contributed to a September skid that ended with the team barely missing the playoffs.

24. Todd Worrell

The Cubs have been tormented by a few great closers. Among the top three in saves against the North Siders are Hall of Famers Trevor Hoffman, the former all-time saves leader, with 38, and Billy Wagner, arguably the greatest left-handed reliever ever, at 25. Sandwiched in between them at 30, however, is a closer who wasn't quite at their level, but shoved it down Chicago's throats throughout his career — Todd Worrell. He posted a stellar 1.79 ERA against them, all while only taking three losses in his 70 1/3 innings of work.

Worrell was a fine reliever across 11 seasons with the Cardinals and Dodgers, posting a career 3.09 ERA and 3.41 FIP and winning Rookie of the Year in 1986. Against the Cubs, though, he pitched as if he belonged in the Hall. The first save of his career was against Chicago as a Redbird, and, in total, 11.7% of his saves were reserved for the Cardinals' rival.

23. Bobby Abreu

Of all players with 150 or more plate appearances at Wrigley Field who have never worn a Cubs uniform, the one with the highest OPS isn't a traditional villain of the team like Albert Pujols or Ryan Braun (foreshadowing!). He's not even the biggest Cubs menace in his team's history. It's instead the deeply underrated Bobby Abreu, with a .333/.416/.682 slash line that adds up to a 1.097 OPS at the Friendly Confines.

Forget Wrigley, though. The lefty outfielder, best known for his time in Philadelphia, absolutely murdered the Cubs overall to the tune of a .323/.432/.638 line in 278 career plate appearances. Making this one extra painful is that Chicago had interest in him in 2009 and could've ensured he spent most of his time hitting in a ballpark that he loved. Instead, they let him leave to the Angels and immediately regretted it when the Halos came to town in the summer of 2010, and Abreu went 4 for 5 with a walk in a 12-0 massacre.

22. Mark McGwire

One of the most absurd statistical standouts among all players to ever face the Northsiders is also tied to a standout moment in their history. While everyone remembers the 1998 home run chase between Cardinals legend Mark McGwire and Cubs slugger Sammy Sosa, McGwire actually didn't play all that many games against Chicago. He only appeared in 42 contests against the Redbirds' bitter rival, and boy did he make every single one count. Big Mac owns the highest OPS against the Cubs of any qualified player with an absurd 1.285, thanks primarily to an .832 slugging percentage.

McGwire accomplished that feat by, unsurprisingly, socking a lot of dingers. He hit 23 long balls against Chicago during his career, including the milestone 62nd homer that cleared Roger Maris' single-season record. For beating Sosa to the record and inflicting nigh-unparalleled damage in such a short time, he deserves to make the cut.

21. Jeff Blauser

Against every other team in baseball, Jeff Blauser was a good player. He accrued a respectable 19.7 WAR over 11 seasons with the Atlanta Braves and two with the Cubs, hitting .262/.354/.405 with a 105 wRC+. In Chicago, though, then-Tribune writer Skip Bayless dubbed him "Jeff Lousy" for his lackluster .226/.343/.342 play to end his career. The shortstop would've been an inner-circle Hall-of-Famer, however, if he could've exclusively played against the North Siders. His .351/.413/.611 slash line in 299 plate appearances ranks as the tenth best among all players with 150 or more PAs.

So notable was Blauser's torture of Cubs pitchers that SABR specifically mentioned his stellar performance against the team in his bio. His most notable feat of destruction came on July 12, 1992, when he posted the only three-homer game of his career against Chicago, including the big three-run shot that flipped the game in favor of Atlanta in the tenth. Despite only appearing in 78 games against the Northsiders, his 15 long balls against them would be tied for his third-highest total over an entire season.

20. Adam Dunn

Adam Dunn is the three true outcomes of baseball made manifest, and he showed the Cubs one of those an awful lot. The longtime Cincinnati Reds slugger hit a home run just over 9% of the time when facing his division rivals, resulting in 43 long balls throughout his career. Nobody with nearly that many dingers against the North Siders has as few at-bats as his 472. The closest is likely Ralph Kiner, who clubbed 46 bombs in 552 at-bats, but he was a Hall of Famer, and that rate still doesn't quite compare.

The flip side is that Dunn accompanied that ludicrous rate of launches with a strikeout rate just under 30%. As such, his slash line of .242/.379/.559 isn't quite as fearsome as other Cubs killers, but that's still markedly better than his career overall. Not to mention, when he hurt the baby bears, he inflicted maximum pain. I could mention any of his climactic blasts with Cincinnati, but his 2012 performance in the twilight of his career with the White Sox, when he hit a home run and walked four times against the North Siders, is a perfect portrait of the Adam Dunn experience.

19. Gary Sheffield

Gary Sheffield bounced around the league for much of his career, but no matter where he was, from Milwaukee to Florida or Los Angeles, he always raked against the Cubs. Slashing .323/.461/.567 against Chicago, he somehow managed to be considerably better than his already impressive career line of .292/.393/.514, or a 141 wRC+. It was about a coin-flip chance that, if Sheff was at the plate, he would get on in some way or another. Sure, only 18 of his 509 long balls came off of North Side pitchers, but he didn't need to wield his prodigious power to be a menace.

On the plus side, the Cubs got to stick it to this killer in 2003. En route to their fateful NLCS appearance against the Marlins, they vanquished Sheffield's Braves in a five-game set and held him to just .143/.294/.143 with a 32 wRC+. Had he performed more like his third-place MVP self that season, perhaps the baby bears would have been sent home before experiencing one of the franchise's darkest hours. On second thought, maybe that makes him an even greater villain in the long run.

18. Brian Giles

Brian Giles has since been a bit forgotten among baseball's greats in recent years. Between his time with Cleveland, the Pirates, and the Padres from 1995 through 2009, the left-handed outfielder put up borderline Hall of Fame numbers overshadowed by the steroid era, with a .291/.400/.502 career slash line, a 136 wRC+, and 54.8 WAR. Instead of Jim Hendry acquiring the underrated masher when he hit free agency in 2005, however, the North Siders spent his entire career getting thrashed.

Giles' .331/.453/.595 line against the baby bears in 396 plate appearances was his fifth-best against any team, though he made a habit of beating up on everyone in the NL Central. What makes him especially torturous for the Cubs, though, is how well he kept it up even as his career wound down in San Diego. No player since the turn of the century with 150 PAs or more against them has an OPS higher than the 1.062 Giles posted through the end of his career. He, of course, turned it on most aggressively when the Pirates were at their most competitive, though.

17. Craig Biggio

One of the Astros' Killer B's was bound to make this list, and Craig Biggio was the obvious answer.
That might come as a shock, since both Lance Berkman and Jeff Bagwell had a higher OPS than the second baseman's .824 against the Cubs. However, the big difference was home runs. Nobody was on the receiving end as often as Chicago, with Biggio crushing 34 long balls off North Side pitchers versus just 22 off the teams right behind them, the Cardinals and Padres.

Fittingly, Biggio's first homer was in the Friendly Confines off of Goose Gossage in 1988, perhaps a harbinger of the horrors he'd inflict. By the time he hung up his cleats, 11.6% of his bombs would be dropped on the baby bears, and he'd record the second most hits of any player in the divisional era against them at 264 across over 1,100 plate appearances. In my mind, he's the ideal of the small, solid-hitting second baseman that always beats the Cubs, an archetype that has haunted Chicago from David Eckstein to Tommy Edman.

16. Nolan Ryan

The Cubs will forever be haunted by the 1969 Miracle Mets that stunned them in one of baseball history's most epic collapses. However, the individual players from that accursed team would continue to plague them for years. For instance, whenever the Ryan Express pulled into town, it often brought devastation for the Chicago bats. The only mercy the legendary Nolan Ryan offered was that his strikeout rate against them was only 8.38 K/9 instead of his career 9.55.

While he may have been the king of K, Ryan didn't need strikeouts to shut out the Cubs. In 34 games, including 30 as a starter, he only took five losses against the Northsiders while twirling a 2.40 ERA in just shy of 200 innings. He could still dial up the swing-and-miss, though, baffling the team even when they were powered by the likes of Dawson and Ryne Sandberg.

15. Lou Brock

Ask any Cubs fan what the team's worst trade of all time is, and there's a near guarantee they'll say Lou Brock for Ernie Broglio. Chicago gave up a future Hall of Famer and former all-time stolen base record holder to their rival for a starter with a career 5.40 ERA and -1.6 fWAR in just over 200 innings pitched on the North Side. The extra salt in the wound? Brock always saved his absolute best for the team that gave up on him.

Brock's .334/.378/.479 in just over 1,100 PAs against his former team adds up to comfortably his best OPS versus any organization in baseball at .856. That comes out to about 27% better than his already excellent career. For fans at the time, it had to be doubly painful watching him blossom into a six-time All-Star and two-time World Series champion as he bludgeoned them with every meeting. Other killers crushed the Cubs more, but nobody ripped their hearts out in the same way he did.

14. Steve Rogers

If you scour the 1970s-80s Montreal Expos, there are more than a few Cubs villains present, from catcher Gary Carter to eventual North Side legend Andre Dawson. In the rotation, though, was a particular thorn in their side — Steve Rogers. The righty spent his entire 13-season career with Canada's team and often found himself on the winning end of matchups against Chicago. His 2.69 ERA against them across 328 innings was nearly half a point better than his career 3.17.

Win-loss record isn't a great indicator of his effectiveness, but the lopsided 21-13 mark he held over the North Siders across 46 games is still the result of his dominance. Entering Olympic Stadium with him on the mound inspired dread, but he often brought the fire to Wrigley Field, where his ERA dropped to just 2.55. However, his most dominant outing was saved for the home crowd, where, in 1982, he held the Cubs to just six hits in a complete-game shutout that killed their momentum from a four-game winning streak.

13. Tom Seaver

Yet another ghost of the 1969 Mets, Tom Seaver was, of course, phenomenal against the Cubs. In 320 2/3 innings, he recorded an excellent 2.51 ERA, but his domination is best showcased by a staggering 299 strikeouts. With the exception of Sandy Koufax, the only pitchers who have sent down more Chicago batters have tossed considerably more innings and, often, finished their careers before Tom Terrific ever stepped on a big league mound.

While his torment lasted throughout his entire career, the worst came in that fateful year. Seaver famously threw one of his best games against the Cubs on July 9, 1969. Only eight years into the Mets' existence and three years into his Hall of Fame run, he punched one of the greatest lineups in team history in the mouth, falling just short of a perfect game thanks to a Jim Qualls single. It was a defining early moment for the fledgling New York franchise at Shea Stadium, and the beginning of disaster for a team that forever left Cubs fans wondering what could've been.

12. Carlos Lee

Though not as imposing as some on this list on paper, few names haunted the nightmares of Cubs fans in the 2000s quite like Carlos Lee in his time with the Astros and White Sox. Lee was a good outfield bat who transcended into a superstar, hitting .294/.353/.552 when he was up against a North Sider. His 24 homers at Wrigley alone were more than he hit against any other team, regardless of park.

But what if you count the damage he did at home, too? Well, El Caballo's 39 bombs overall versus the Cubs are over double what he had against the next highest team at 19. He made them count, too. From the 10th-inning walk-off grand slam he hit on the South Side in 2001 to the 4th-inning three-run jack into the Crawford Boxes that won the game for Houston in 2008, he was often a one-man wrecking crew that dashed fans' hopes whenever he faced their favorite team.

11. Dwight Gooden

On the one hand, Dwight "Doc" Gooden didn't perform as spectacularly as some pitchers when facing the Cubs. In 284 1/3 innings across 40 games and 39 starts, he ended with a career 3.32 ERA against the baby bears. That's good, but there are more deserving on that front. No, the real reason he makes this list is his record. He only lost four times to Chicago and picked up 28 wins.

Again, I'm not a believer in wins as an ideal stat to evaluate pitchers. However, in talking about Cubs killers, it's fair to acknowledge an outlier. The only pitchers with a better win rate than Gooden's over the team didn't pitch as many innings and, save for one to be discussed, weren't as good. The fact is, for nearly 300 innings, the Mets hurler pitched better than his career ERA and won a higher percentage of games than against any other team he faced more than ten times. In his Cy Young-winning 1985 season, Doc also saw the Cubs five times and threw for a complete game every time with a 1.00 ERA.

10. Ryan Braun

It would be malpractice to not include a prominent Milwaukee Brewer in an era when they've become the Cubs' number one tormentor. Of the possible options, no one deserves the honor of chief torturer as much as Ryan Braun. Fans at the Friendly Confines saw a lot of the 2011 MVP across 193 games from 2007 through 2020, and he gave them many reasons to boo. With a .311/.387/.558 slash line and 40 long balls, he was the perfect villain to be the face of an organization on the rise.

One of those home runs set the tone early for his status as a player fans loved to hate. In 2008, with the Brewers seeking their first playoff appearance in 26 years, he took Cubs reliever Bob Howry deep to break a one-one tie in the eighth to punch their ticket to the postseason. Even as his career wound down, though, he kept turning back the clock when it was time to play Chicago. It's not like Wrigley contained him either, as he hit a similarly impressive .321/.373/.554 in enemy territory.

9. Rogers Hornsby

In the timeless rivalry that is the Cardinals and Cubs, I'd argue Rogers Hornsby is the first true Cubs killer to play for the Redbirds. They've had good players before him who have dominated the North Siders, but none who did so to such a degree that, despite also playing very well for Chicago, he's still remembered for the destruction he wrought against the team that plays at Wrigley Field. The Rajah of Swat felt as if he was setting the tone for this rivalry, and it was not a good one if you liked the guys in blue more.

Across 989 plate appearances, he still has the sixth-highest OPS among qualified batters, with a .364/.437/.592 slash line. Hornsby put up absurd numbers against, well, everybody, but of his division rivals, that's still the second-best line he recorded, behind only the Phillies. The Cubs had to watch him become the superstar of not just the Cardinals, but the NL as a whole, beating down their pitchers along the way with 40 home runs against them. Few players took over Wrigley like he did, with a .352/.438/.591 line in the historic ballpark.

8. Frank Robinson

The legendary Frank Robinson put up no shortage of monster seasons, primarily with the Cincinnati Reds and Baltimore Orioles. However, coincidentally, his 1.048 OPS against the Cubs across 202 games is just one point better than his best offensive season by the stat. Truly, he saved his very best for Chicago, and that involved the tenth-most home runs of all time against the team at 54. No team experienced his power more than the Northsiders, and when he left the yard, he did so in bunches.

Robinson is one of only two players ever with two seasons of nine or more homers against the Cubs. One season of nine long balls inflicted upon a single team is already exceedingly rare. Just eight batters have done it to the Cubs overall, with the last being Joey Votto in 2021. Players who never accomplished the feat include sluggers like Pujols, Hornsby, Willie Mays, and Hank Aaron. That, alone, earns Robinson a Chicago ownership license.

7. Randy Johnson

The Big Unit dominated many teams at the height of his powers, yet not once did he ever let the Cubs up for air. Randy Johnson is the only pitcher to throw over 100 innings against the North Siders and not once suffer a loss, going a perfect 13-0 and effectively sweeping them for his career. Ok, that's not entirely accurate, since he pitched in 15 games, but the only game Chicago ever won in which he was involved was when he made a one-inning relief appearance for the Giants in his final season.

Wins and losses are a little luck-based, sure, but Johnson didn't have to get that lucky, considering the Hall of Famer had a 1.91 ERA when facing the Cubs. He didn't just beat them, either. He mowed down this team, recording nearly 40 more strikeouts than innings pitched. Forget starters. The only qualified pitchers with a higher K/9 than his 12.41 against Chicago are relievers, namely Octavio Dotel and Josh Hader. Their only saving grace was that much of his career was spent in another division.

6. Hank Aaron

Hammerin' Hank Aaron, the former home run king, unsurprisingly hit a lot of long balls against the Cubs. So many, in fact, that his 87 big flies is second most all-time against the team and accounts for 11.5% of his towering career total of 755. It wasn't just about the hits that left the yard, though. The legendary Brave's .326/.376/.589 line was better than he performed against any team save for the Reds and Padres.

For Cubs fans of the time, he was best remembered for utterly dominating their pitching at Wrigley. 50 of his homers were hit within the Friendly Confines, making him one of only three non-Chicago players to cross that mark in his career. Without spoiling who's to come, the other two are still remembered as legendary crushers of North Side dreams, meaning he deserves to share their company.

5. Stan Musial

Stan "The Man" Musial is the picture of steady excellence, and that was very much true of his performance against the Cubs. While he gets some points docked as a villain for being better against most of the other NL teams, he still saved a lot of jaw-dropping performances for Chicago across a 126.4 WAR career. Sure, he may have struck more fear into the hearts of Dodgers pitchers, but a 317/.400/.539 performance across nearly 1800 plate appearances is nothing to scoff at.

Musial's 67 home runs against the Northsiders remains in the top five all-time, but most telling of his annoyance factor has to be his RBIs. No player comes particularly close to the 286 he drove in off of Cubs arms. That's partly due to just playing so many games against them, but it paints a picture of who he was. From his dazzling performance as a rookie in 1941 to his 3000th hit at Wrigley Field in 1958, he was always "The Man" when a clutch hit was needed.

4. Joey Votto

Don't let Joey Votto's excellent turn as an analyst distract you from the fact that he was a cold-blooded killer of the Cubs. Since his debut in 2007, the Cincinnati Reds legend was truly automatic, slashing .308/.414/.575 in just shy of 1,000 plate appearances versus the team. By OPS, he's also just outside the top ten best hitters at Wrigley with 150 or more PAs. The biggest notch in his favor, of course, is that he was a career Red and thus kept this domination up longer than just about anyone since the turn of the century.

Staying in the Central allowed him to rack up 50 home runs and the eighth-most doubles against Chicago with 67. Votto also had a habit of reaching milestones off of the Cubs, including his 300th home run and 2,000th hit. As mentioned above, he's also recorded a nine-homer season against Chicago and became the second player in history to reach base nine times in a day during a doubleheader with them in 2015. Although I love him, I can't say that extended to when he was in the batter's box against my favorite team.

3. Albert Pujols

First base, for my money, might have the highest volume of Cubs killers of any single position. Atop that mountain, without question, is Cardinals slugger Albert Pujols, who not only was a franchise standout of Chicago's greatest rival, but never seemed to fail when his team needed a hit. Pujols didn't do anything too out of the ordinary for his extraordinary 89.9 WAR career, but his .292/.394/.605 slash line facing the North Side was to be feared.

Pujols ended his career in 2022 with 703 home runs, and a whopping 59 of those came against the Cubs. He didn't waste time proving he was going to be a problem for fans at Wrigley, either. In 2004, he was at the center of a wild one at the Friendly Confines, clubbing three-homers in a five-hit day to help the Cardinals come back from down 8-2. 2011 later saw him torture the boys in blue with not one, but two walk-off home runs in a row. Even in 2022, with Pujols chasing one more milestone before retirement, he still found a way to hurt his old foes one last time in the eighth inning of a game in September to cap off a sweep.

2. Mike Schmidt

For a generation of Cubs fans, and even for many fans today, Mike Schmidt is still revered as the ultimate killer. Regarded by many as the greatest third baseman to ever live, the Phillies legend slashed .292/.387/.598 when playing his division rivals and clubbed 78 home runs in 1,142 plate appearances, good for third all-time. That makes him by a country mile the leader in home runs against Chicago among players who started their careers in the divisional era.

Remember how I mentioned two players posted two nine-homer seasons against the Cubs? Well, Schmidt was the other. Except one of his was also a ten-homer campaign. Schmidt's big flies were also the backbone of some dramatic Phillies wins over Chicago. He clubbed four into the Wrigley bleachers — his first wasn't until the fifth inning — on April 17, 1976, helping power a Philadelphia comeback from down 13-2, the largest in NL history. However, most will likely remember him as the man who delivered the final blow in the highest-scoring MLB game ever, taking Bruce Sutter deep in the tenth to win the infamous 23-22 contest on May 17, 1979.

1. Willie Mays

At the end of the day, it's not a Cardinal, a Brewer, a Red, or a Pirate at the top of the list, but one of the greatest players of all time who made a habit of destroying the Northsiders. Willie Mays remains one of the few hitters in the conversation for greatest of all time. His overall numbers and 149.8 career fWAR are to be marveled at, but against the Cubs, he was especially brilliant. Only four players have more PAs against them than the Say-Hey Kid's 1,515, yet nobody in that ballpark has an OPS that can rival his pristine 1.000.

A big reason he's at the very top is the sheer number of long balls he's recorded, taking Cubs pitchers deep 92 times, five more than the next highest all-time. 54 of those jacks also came at, you guessed it, Wrigley Field, the most of any non-Cub. The Friendly Confines were especially friendly to Mays, as he also has the third-highest OPS among players with 150 or more plate appearances at 1.077. He had more than a few memorable moments at the Cubbies' expense, too, including hitting his first home run in San Francisco in 1958.

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