Cubs’ sweetest memory came in 2016

We’re about a quarter of the way through the 21st century, and already Cubs fans have experienced extreme highs — winning the World Series — and devastating heartbreak — watching the Curse of the Billy Goat work its magic.

Now in 2025, there are plenty of ways to reflect. One could chart a timeline, or plot a by-the-numbers breakdown, or create a highlight reel. One could acknowledge top Cubs players this century — a list that includes Kerry Wood, Mark Prior, Aramis Ramirez, Sammy Sosa, Derrek Lee, Anthony Rizzo, Kris Bryant, Javy Baez, Jon Lester and Willson Contreras.

The Sun-Times decided to pick out moments — 25 of them — that define this quarter century of Cubs baseball. Some are fond memories for Cubs fans. Some are closer to nightmares. Some set the trajectory of the team for years to come. And some are just entertaining stories to tell.

25. May 27, 2021

Javy Baez was aptly nicknamed “El Mago” for the magic he regularly performed on the field. That talent reached absurd heights against the Pirates when he made their first baseman forget the rules of the game.

With two outs in the third inning and Willson Contreras on second, Baez grounded to third, and the throw easily beat him to first. So he stopped and ran backward. If Pirates first baseman Will Craig had stepped on the base, the inning would’ve been over. Instead, he chased Baez all the way down the line, giving Contreras a chance to score. As the Pirates threw the ball around, Baez reached second.

24. Oct. 4, 2007

The image of Ted Lilly spiking his glove after giving up a go-ahead home run to the Diamondbacks’ Chris Young in the second inning of Game 2 of the National League Division Series is seared into Cubs fans’ brains. It encapsulated that disappointing postseason.

The Cubs had gone from finishing last in the NL Central in 2006 to winning the division in 2007. But the Diamondbacks steamrolled them in the NLDS. In a three-game sweep, the Cubs were outscored 16-6.

23. Sept. 15, 2015

Cubs manager Joe Maddon launched into a diatribe against the Cardinals after an 8-3 win during which the teams traded plunkings. Maddon torched the division rival for retaliating.

“We don’t start stuff, but we will stop stuff,” he said.

Maddon also took issue with Cardinals infielders playing behind the baserunners when the Cubs were up by five runs late in the game, warning that next time they would steal.

“I was a big Branch Rickey fan, but I never read this book that the Cardinals had written regarding how to play baseball,” Maddon said.

22. Aug. 22, 2010

Cubs manager Lou Piniella had made clear in July that the 2010 season would be his last at the helm. But after missing four games in August to spend time with his ailing mother, he moved up his plans.

Piniella, known for his outbursts and colorful ejections, was teary-eyed during his last game. It was No. 3,598, including the playoffs, in a 23-year managerial career with the Yankees, Reds, Mariners, Devil Rays and Cubs. He amassed a .517 regular-season winning percentage and won the 1990 World Series.

21. July 10, 2014

Anthony Rizzo tossed aside his glove and threw down his hat as he strode toward the home dugout at Great American Ballpark.

Tensions were high between the Cubs and Reds after brush-back pitches from Reds reliever Aroldis Chapman. The Cubs voiced their displeasure, but Chapman waved them off. The Cubs took the field, and Rizzo heard something that made him charge.

Some point to Rizzo deciding enough was enough as a cultural turning point in the rebuild. Either way, it endeared him to Cubs fans.

Two years later, the Cubs would acquire Chapman at the trade deadline with a World Series push in mind.

20. June 19, 2003

Speaking of brawls with the Reds, a famous one began with a tussle between Cubs pitcher Kyle Farnsworth and Reds pitcher Paul Wilson. After Farnsworth’s pitch sailed up and in at Wilson, who had squared to bunt, they exchanged words and ran at each other.

Farnsworth tackled Wilson and threw a punch before they were separated by teammates. Farnsworth walked away smiling and jawing, while Wilson was left with a cut on his nose and blood splattered on his jersey.

It was a year of notable NL Central spats. Less than three months later, during a massive five-game series between the Cubs and Cardinals, Cubs manager Dusty Baker and Cardinals manager Tony La Russa got into a shouting match across the field over hit batters on both sides.

19. May 20, 2006

Sticking with the theme, who could forget Cubs catcher Michael Barrett punching the White Sox’ A.J. Pierzynski, heightening tensions in the crosstown series?

Pierzynski tagged up on a sacrifice fly and barrelled into Barrett at home, slapping the plate after the collision. Then Barrett threw his haymaker, and the dugouts cleared.

18. Oct. 3, 2004

The Cubs’ 2004 collapse featured a unique twist. Before the season, Sports Illustrated picked them to win the World Series, featuring Kerry Wood on the cover of its baseball preview.

They would go on a five-game losing streak in the last week of the season, finishing third in the division with an 89-73 record.

Infamously, Sammy Sosa arrived late to the season finale and left early.

17. Feb. 25, 2016

Reports swirled in February 2016 that Dexter Fowler was joining the Orioles on a three-year deal after rejecting the Cubs’ qualifying offer.

Then he showed up at the Cubs’ spring-training complex, surprising his teammates, whom Maddon had gathered around the pitcher’s mound.

Fowler would become an All-Star that season and etch his name in the record books with the first Game 7 leadoff home run in World Series history.

16. Oct. 3, 2018

One line from president of baseball operations Theo Epstein’s end-of-season comments would reverberate over the next several years as the Cubs tried to reclaim the magic of 2015-17. The team had just lost the wild-card game to the Rockies 2-1.

“Our offense broke somewhere along the lines,” Epstein said.

The team fired hitting coach Chili Davis a week later. That was the beginning of the end for Maddon, who would enter the next season as a lame-duck manager.

In 2019, the Cubs had control of a wild-card spot in late September before going on a nine-game skid. They went 2-10 to finish the season, snapping a four-year playoff run.

15. Oct. 1-4, 2008

After the disappointment of 2007, 2008 surely would be different, right? The Cubs finished the season with the NL’s best record (97-64) by a wide margin.

Then they met the Dodgers, whom the Cubs swept in May at Wrigley Field, in the NLDS. But the Dodgers won both playoff games at Wrigley, rallying to take Game 1 on James Loney’s grand slam and exploiting four Cubs errors to blow out Game 2.

14. Sept. 14, 2008

The game between the Cubs and Astros moved to Milwaukee’s Miller Park after Hurricane Ike swept through Houston.

The Cubs had a six-game lead in the NL Central, and the Astros, a division rival, were in the mix with the Brewers and Phillies for a wild-card spot. The Astros were the home team, but because of the game’s proximity to Chicago, it was a Cubs-friendly crowd.

Cubs starter Carlos Zambrano hadn’t pitched in almost two weeks because of a shoulder strain. But there was no easing back in for him. His no-hitter included 10 strikeouts, and he retired the last 13 batters.

13. Nov. 6, 2023

Most managers aren’t usually covered like players in free agency. But considering Craig Counsell’s track record in Milwaukee, he wasn’t most managers.

In the fall of 2023, reports followed Counsell’s meetings with the Mets and Guardians, as well as the Brewers’ interest in retaining their manager. Then a mystery team entered the equation.

To kick off the general managers meetings, the Cubs fired David Ross to hire Counsell in one fell swoop. The move was made more stunning by the team’s praise of Ross during his three years as manager. A fan favorite from the World Series team, Ross led the Cubs to a division title in the COVID-19-shortened 2020 season, his first at the helm.

12. June 3, 2003

In the first inning of a game against the Devil Rays that the Cubs would go on to win 3-2, Sosa splintered his bat on a groundout. The cork in the core of the bat was left exposed, and Sosa was ejected.

Sosa insisted he used the corked bat only for batting practice and accidentally picked it up that day. None of his other bats were found to be corked.

The incident became a national story. But it was dwarfed years later, when the New York Times reported that also in 2003, Sosa was one of over 100 players who tested positive for a performance-enhancing drug in an “anonymous” MLB survey.

11. Sept. 27, 2001

In the days after Sept. 11, the nation grieved together with so many touched by the tragedy. And for the Cubs’ first home game after the attacks, Sosa carried an American flag as he took the field in an emotional moment for those in attendance and watching from home. When he homered later in the game, he again carried a flag with him around the bases.

It was one of the most memorable moments of Sosa’s career — which included a 20-homer month in the midst of the 1998 home-run chase — for the connection he forged with fans at such a painful time.

10. Oct. 25, 2016

The outfield collision that tore two ligaments in Kyle Schwarber’s left knee in April was supposed to end his season. But about six months after surgery, he stepped into the Progressive Field batter’s box in Game 1 of the World Series.

He went a stunning 7-for-17 (.412) in the series, recording three hits in Game 7. His leadoff single in the 10th inning started the rally that clinched the title for the Cubs.

9. Dec. 10, 2014

Jon Lester’s six-year, $155 million deal with the Cubs came together in the wee hours of the morning at the winter meetings in San Diego. Not only had the Cubs landed an ace, but they’d convinced the two-time World Series champion that they were ready to take the next step. With him, they became legitimate playoff contenders.

Lester would go on to post a 3.64 ERA in six years with the Cubs, earn two more All-Star selections and, of course, lead the team to a World Series title. His signing would go down as one of the best in Cubs history.

8. Oct. 15, 2016

Cubs catcher Miguel Montero didn’t even think he was going to get to hit when he strode toward the batter’s box that October night with the bases loaded and Game 1 of the NL Championship Series tied at 3 in the eighth inning.

Pinch-hitting for closer Aroldis Chapman, Montero assumed the Dodgers would make a pitching change and Maddon would have to counter. That didn’t happen.

Montero drove the third pitch of the at-bat into the right-field bleachers. It was the third pinch-hit grand slam in postseason history and the first to claim the lead.

Also in that game, which the Cubs won 8-4, Javy Baez became the first Cub to steal home in a postseason game since Jimmy Slagle in the 1907 World Series.

7. Oct. 22, 2016

No moment in Kyle Hendricks’ 11-year Cubs tenure encapsulated “The Professor’s” unwavering composure quite like Game 6 of the 2016 NLCS against the Dodgers.

The Cubs were one win away from claiming their first trip to the World Series since 1945, and the 26-year-old was matched up against three-time Cy Young winner Clayton Kershaw.

The Cubs scored all five of their runs against Kershaw. And Hendricks held the Dodgers to two hits in 7⅓ scoreless innings.

No other pitcher in postseason history had thrown seven-plus innings while allowing two or fewer baserunners in a potential clincher.

6. Oct. 7, 2015

Jake Arrieta’s wild-card shutout against the Pirates would have been plenty notable on its own, but a social-media interaction before the game showed just how much bravado he carried into his first postseason appearance.

A parody account of the Pirate Parrot tweeted at Arrieta to “be ready for the sea of black,” in reference to the blackout game at PNC Park, with a string of hashtags, including “#crowdisGoingToEatYoualive.”

Arrieta responded, “Whatever helps keep your hope alive, just know, it doesn’t matter.”

He more than backed up that statement, striking out 11 in nine innings of dominance and sending the Cubs to the NLDS. That performance was the icing on a regular season that earned Arrieta the NL Cy Young Award and included his first no-hitter.

5. Oct. 13, 2015

It was clear the Cubs had an exciting young team in 2015. It wasn’t obvious just how far it would go. But after losing the first game of the NLDS in St. Louis, the Cubs rattled off three straight victories, claiming a berth in the NLCS with a 6-4 victory at Wrigley Field.

Facing John Lackey for the second time in the series, the Cubs put together a four-run second inning. Starting pitcher Jason Hammel initiated the scoring with an RBI single. Then Baez launched a three-run homer into the right-field bleachers to give the Cubs the lead.

The Cardinals would tie the game in the sixth, but the Cubs answered immediately with a solo homer from Anthony Rizzo that put them ahead again.

That offseason, Lackey and Jason Heyward would leave the Cardinals in free agency and join the Cubs.

4. July 29-30, 2021

Two scenes defined the Cubs’ 2021 teardown.

Rizzo was the first to go. After the Cubs dealt him to the Yankees, Rizzo walked back onto the field with his family.

The team was heading to Washington, where they’d face the Nationals on deadline day. But Rizzo got to soak in a few final moments at Wrigley Field before he closed such a momentous chapter of his career. He leaned back against the ivy growing on the brick outfield wall.

The next day, Kris Bryant was spotted on the phone in the Nationals Park visitors dugout. He hung up and hugged hitting coach Anthony Iapoce after being traded to the Giants. The Cubs also traded Baez to the Mets.

It was clear as the deadline drew near that the Cubs wouldn’t continue with all three on the roster in walk years, but losing all of them was stunning.

It also ushered in a new era for the Cubs, with a prospect haul coming back that included Pete Crow-Armstrong, Kevin Alcantara, Alexander Canario and Caleb Kilian.

3. Oct. 12, 2011

Bringing in Theo Epstein as president of baseball operations was arguably the most influential move the Cubs have made in the last 25 years.

“I firmly believe that we can preserve the things that make the Cubs so special and over time build a consistent winner, a team that will be playing baseball in October consistently,” Epstein said in his introductory news conference, “and a team that will ultimately win the World Series.”

He delivered on his promise. And though his rebuild plan included growing pains, with the Cubs losing 101 games in Epstein’s first year and 96 the next year, the team went on to punch its ticket to the postseason five times in six years. The Cubs went to the NLCS three consecutive times and won the 2016 World Series.

Epstein stepped down after the 2020 season and handed over the reins to his second-in-command. Jed Hoyer has been leading the baseball operations department ever since.

2. Oct. 14, 2003

One of the most infamous moments in Cubs history, the Steve Bartman incident was a tale of heartbreak. And Bartman, a fan himself, became the target of the fan base’s ire for years to come.

Bartman sat down the left-field foul line at Wrigley Field for Game 6 of the 2003 NLCS against the Marlins. The Cubs led the series three games to two and were up 3-0 with one out in the eighth inning. They were five outs from punching their ticket to the World Series.

The Marlins’ Luis Castillo hit a fly ball down the line in foul territory, and Cubs left fielder Moises Alou tracked it to the side wall. He leaped. He reached. But so did Bartman.

Despite Bartman’s deflection, it was called a foul ball, not fan interference, because it was outside the field of play. The Cubs fell apart. They gave up eight runs in the inning and lost 8-3. They lost 9-6 in Game 7.

1. Nov. 2-3, 2016

There were times during a long and — fortunately for the Cubs — rainy Game 7 of the 2016 World Series when it seemed like they were still cursed: two runs scored on a wild pitch by Lester. Chapman entered in the eighth and immediately gave up an RBI double to Brandon Guyer and a game-tying home run to Rajai Davis. The momentum had swung wildly from Chicago to Cleveland.

The rain had other plans.

The Cubs’ players and coaches who witnessed Heyward’s famous speech still talk about the confidence in the conversations in the weight room behind the dugout as they took shelter during the delay. They weren’t trying to manage the grandeur of the moment; they were seizing it.

When they reemerged, the game was knotted at 6. The Cubs regained the lead with RBI hits from Ben Zobrist and Miguel Montero. In the bottom of the inning, Cleveland cut the lead to one. But then, mercifully, Mike Montgomery induced Michael Martinez to hit a grounder to third base with two outs.

“A little bouncer, slowly toward Bryant,” Hall of Fame announcer Pat Hughes said in his famous radio call. “He will glove it and throw to Rizzo. It’s in time! And the Chicago Cubs win the World Series!”

It was their first title since 1908.