Chicago Cubs History: Ranking the Theo Epstein era’s top 10 moments

Entering a new era under Jed Hoyer is not an easy pill to swallow. Considering the fact the Chicago Cubs have not won a postseason game since 2017 and are now entering “rebuild/retool mode” in what was supposed to be a contention window, there is much disappointment among fans. After 2016 it looked like the Cubs could be the next baseball dynasty. In the end, they were not.

It might be hard to look at this team at the moment and feel sentimental about them. 2016 was supposed to be just the beginning, and now the Cubs are now drawing comparisons to the 1985 Chicago Bears. A young team with so much promise after a championship win, ending up being one-and-done and eventually fading into oblivion. Like the ending of the Ditka-era Bears, this ending has not been particularly pretty. A sad ending to a story that once held so much promise.

With all of that said, this era of Cubs baseball was still the best any living fan had ever seen.

From 2015-2020, Chicago made the postseason five out of six years, won six playoff rounds (WC and series), won 92+ games in four consecutive years (2015-2018), and of course, won that elusive World Series title we had all waited for. If someone told me the Cubs would go on that kind of run back in 2014, I would have been ecstatic. The recent shortcomings are still very upsetting, but remembering the good times is what fans should do as we enter a tough road ahead for the rest of 2021 and beyond.

Here is a top 10 list of moments this core had. As usual, this list is up for conversation and debate.

Chicago Cubs: We enter our postseason moments, including crazy games and more grand slams

#7. Clinching the 2017 NLDS against the Washington Nationals – 10.12.17

The team’s last postseason series win came in the 2017 NLDS against a very good Nationals team. In a back and forth five-game series, the defending champion Cubs prevailed. Game 5 was a wild one at Nationals Park, ending in a high-scoring 9-8 win. It looked grim early as the Nationals took a 4-1 lead in the second, but the Cubs chipped away thanks to some timely hits and Nationals miscues, and they eventually took the lead. The Cubs would open up leads of 8-4 and 9-6, but Dusty Baker’s Nationals would not go away. A big double play ball off the bat of Adam Lind, followed by Willson Contreras picking off Jose Lobaton in the eighth helped the Cubs preserve a precarious 9-8 lead. Closer Wade Davis sailed smoothly in the ninth, eventually striking out Bryce Harper to end the game and series. It was a near five hours of torture, but Cubs fans were used to heart-pounding postseason games on the road. This marked the first time in Cubs history the team won a postseason series three years in a row.

#6. Miguel Montero NLCS Game 1 grand slam against the Lost Angeles Dodgers – 10.16.16

Here is a postseason moment that is not from a series-clinching game. Miguel Montero’s pinch-hit heroics in the first game of the 2016 NLCS will go down in history. One could argue it is the biggest, or at least most exciting, home run in Cubs postseason history. It was the bottom of the eighth in Game 1, score tied at three. The Cubs had just lost a 3-1 lead in the top of the eighth and were looking to take it back. They loaded the bases against veteran Joe Blanton, and Montero came up with two outs. Blanton got ahead 0-2 before delivering a flat slider to Montero, which he crushed to the back of the right field bleachers. Wrigley Field was shaking as the veteran catcher rounded the bases. The crowd was still celebrating when Dexter Fowler swung at the first pitch of his at bat and hit a solo shot off the digital boards in the right field corner. Cubs won 8-4 and took a 1-0 series lead.

Now for our top five!

Chicago Cubs: When the Pirates fans tried to use home field advantage to get into the Cy Young winner’s head, he assured everyone it wouldn’t matter

10.7.15. The first postseason game for the Cubs since 2008 would take place at PNC Park in Pittsburgh. Despite winning 97 games that year, the Cubs would have to face the division rival Pirates in the one-and-done NL Wild Card game. Jake Arrieta against Gerrit Cole.

PNC Park was “blacked out” with some splotches of Cubs blue in the stands. The Pirates faithful were loud and proud in the pregame as they wanted to give their team as much of an advantage as possible. Arrieta and the Cubs were not phased and quickly turned the cheers into silence.

Arrieta got an early 1-0 lead before taking the mound thanks to an RBI single by Kyle Schwarber, scoring Dexter Fowler two batters in. Schwarber’s next trip to the dish in the top of the third ended with him hitting a titanic two-run blast completely out of the ballpark and into the Allegheny River. Fowler added a solo homer in the fifth to make it 4-0 Cubs. As for Arrieta, he would go on to pitch a complete game, five-hit shutout. He struck out 11 batters and walked none.

The Pirates hitters were flustered all night, and even a bases-loaded threat in the sixth inning did not phase Arrieta. Nor was he phased by getting thrown at, resulting in a benches-clearing situation, in the seventh. (RIP Pirates Gatorade cooler) Pirates catcher Francisco Cervelli lined out to Starlin Castro for the 27th out, as Arrieta and the Cubs mobbed each other on the field.

Ironically, this would be the final MLB game in the career for former Cubs All-Star Aramis Ramirez, who finished his career with the Pirates, the same team that traded him to the Cubs in 2003.

This was the Cubs’ first postseason win since 2003.

Chicago Cubs: What looked like the makings of yet another postseason collapse, the 2016 team proved they were not like the teams of Cubs past

10.12.16. The story of the 2016 Cubs postseason run began with an epic series against the San Francisco Giants. Taking the first two games at Wrigley Field, which saw Javier Baez hit a game-winning solo shot in Game 1 and a Travis Wood home run in Game 2, the Cubs needed just one more win to advance to the NLCS as the series shifted to San Francisco. Game 3 ended in heartbreak as the Cubs lost the lead in the eighth inning and eventually lost the game in extra innings, setting up Game 4. John Lackey against Matt Moore.

Veteran catcher David Ross provided both Cubs runs in the first eight innings with a solo home run and a sac-fly, but they trailed 5-2 in the ninth. Moore pitched eight innings of two-run ball and struck out 10 Cub hitters on 120 pitches. If Chicago could not pull off a miracle, they would have to play a winner-take-all Game 5 at Wrigley Field and likely face both Johnny Cueto and MadBum. Giants fans were all up and loud as they felt like “even year” magic was unfolding for them yet again. The Giants had roughly a 97 percent win change entering the ninth. Not. So. Fast.

Enter the shaky Giants bullpen.

Derek Law comes in and gives up a single to Kris Bryant. Javier Lopez replaces Law and walks Anthony Rizzo. Sergio Romo replaces Lopez and gives up an RBI double to Ben Zobrist, cutting the San Francisco lead to 5-3. Will Smith replaces Romo and gives up a game-tying RBI single to Willson Contreras. Jason Heyward bunts, forceout at second, but Heyward makes it to second on Brandon Crawford throwing error. Hunter Strickland replaces Smith and gives up a go-ahead RBI single to Javier Baez. Ross grounded into a double play to finally end the inning.

Cubs went from 5-2 down to leading 6-5 in a matter of five pitching changes. The visitor’s dugout was going nuts as they were on the verge of the NLCS. It was not time to celebrate just yet though, the Giants still had three more tries to tie or win it. Aroldis Chapman would shut down the Giants as he struck out Gorkys Hernandez, Denard Span and Brandon Belt all swinging to clinch the series and advance to the NLCS. One of the best comebacks seen in a modern postseason game.

This marked the first time in team history the Cubs made it to the NLCS in consecutive years.

Chicago Cubs: Outside of winning the World Series, beating the rival Cardinals in the postseason might have been the sweetest feeling in the world for Cubs fans

10.13.15. Wrigley Field was buzzing with anticipation as the Cubs held a 2-1 series lead over the 100-win Cardinals in the NLDS. The game began at 3:38 PM and the 101-year old ballpark was drenched in a golden glow from the Chicago October sunset. John Lackey taking on Jason Hammel.

Stephen Piscotty hit a two-run shot in the top of the first to give the Cardinals a 2-0 lead, but the Cubs rallied for four runs in the bottom of the second. Javier Baez hit his first career postseason home run, a three-run homer, to the opposite field to cap off the second inning rally. Wrigley Field was shaking violently as Baez ran the bases, and Lackey had steam coming out of his ears. The Cardinals tied it up in the top of the sixth, but Anthony Rizzo gave the Cubs the lead back in the bottom of the inning with a solo home run to right. 5-4 going to the seventh.

Then, Kyle Schwarber cemented his legacy in Cubs history.

Leading off the bottom of the seventh, Schwarber turned on a 1-1 Kevin Siegrist pitch and blasted it on top of the right field video board. While only a solo shot in the scorecard, it felt like it was worth so much more. Following the seventh, Pedro Strop shut down the eighth inning, and closer Hector Rondon came on to close it in the ninth. He got Tony Cruz to groundout, Mark Reynolds to strikeout, gave up a single to Matt Carpenter, then struck out Piscotty on three pitches to clinch it.

This victory marked the first postseason series win for the Cubs at Wrigley Field. It also broke a streak of four consecutive years the Cardinals made it to the NLCS or further. The “Lovable Losers” took down the closest team the National League has to the New York Yankees. For once, the Cubs were truly “on top” in the rivalry. It was a joyous night in Wrigleyville as the fans flooded the streets in celebration.

Chicago Cubs: First pennant win since 1945 came easily thanks to Kyle Hendricks

10.22.16. The last time the Cubs had a 3-2 series lead in the NLCS was 2003…and everyone remembers how that ended. That was not going to happen this time, and Cubs fans would experience little stress in this one.

Kyle Hendricks, the season ERA title winner, against All-Star Clayton Kershaw.

The Cubs got to Kershaw early with two runs in the first. Kris Bryant drove in the first run, and an Andrew Toles error set up a Ben Zobrist sac-fly. Dexter Fowler drove in a run in the bottom of the second with an RBI single. Willson Contreras hit a solo homer to left in the fourth and Anthony Rizzo hit one to right in the fifth, chasing Kershaw out of the game. Five runs (four earned) on seven hits off the three-time Cy Young winner.

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Meanwhile, Hendricks was dominating. He had the Dodgers off balance all night, getting outs and getting them quickly. He faced the minimum through seven innings, erasing a hit and a Javier Baez error with a double play ball and pickoff. Starting in the third inning, Hendricks retired the side five straight innings. With one out in the eighth, he gave up a groundball single to Josh Reddick and was pulled by Joe Maddon. The crowd gave him a roaring ovation as he walked to the dugout with Aerosmith’s “Sweet Emotion” playing over the Wrigley sound system.

Hendricks pitched 7.1 innings, 2 H, 6 K, 0 BB, 0 ER, 0 runs on 88 pitches. 57 strikes, 10 groundballs, seven flyballs, one line drive. He was responsible for only two Dodgers baserunners and not a single Dodger got into scoring position.

Aroldis Chapman would come on to get the final five outs. He induced a double play off the bat of Howie Kendrick to end the eighth. In the ninth, he struck out Kike Hernandez, walked Carlos Ruiz and then got Yasiel Puig to ground into a game-ending 6-4-3 double play.

“He’ll [Puig] hit a groundball towards short, Russell goes to Baez one, over to first…the Cubs are going to the World Series!” -Cubs radio play-by-play man Pat Hughes

42,386 fans at Wrigley Field, along with thousands more in the streets and Wrigleyville bars, all sang “Go Cubs Go” together as fireworks blasted in the sky. The ceremony on the field included interviews with Tom Ricketts, Theo Epstein and many of the players. It was arguably the greatest night in Wrigley Field history.

Chicago Cubs: There are a lot of other great moments that can be included on a top-list, so here are some honorable mentions before we get to our number one

Kyle Schwarber defeats the Reds at Great American Ballpark – 7.21.15

The rookie was playing in just his 11th career MLB game when he blasted a game-tying home run in the ninth, and then followed up with a game-winning homer in the 13th inning.

Cubs slug six homers against the Cardinals in Game 3 – 10.12.15

In their first postseason game at Wrigley Field since 2008, the young Cubs won 8-6 and took a 2-1 series lead in the NLDS behind six home runs. Those home runs were hit by: Kyle Schwarber, Starlin Castro, Kris Bryant, Anthony Rizzo, Jorge Soler and Dexter Fowler.

Jon Lester walk-off squeeze bunt vs. the Mariners – 7.31.16

In a game that saw the Cubs face an early 6-0 deficit and a catch at the wall in left by pitcher Travis Wood, it was only natural the ending would be crazy. After rallying and tying the game in the ninth, the game went to extras. Jon Lester was called upon to pinch-hit and lay down a squeeze bunt with Jason Heyward at third, he executed perfectly and Heyward scored the winning run.

Javier Baez game-winning solo home run against the Giants – 10.8.16

Game One of the NLDS in 2016 saw a pitcher’s duel between Jon Lester and Johnny Cueto. 0-0 in the eighth inning, Javier Baez blasted a deep drive to left, which fought the brisk Fall wind, but still landed delicately in the basket in the well area for a solo home run. Cubs took a 1-0 series lead with a 1-0 win.

Cubs clinch NL Central in St. Louis – 9.27.17

The defending champion Cubs needed to win just one more game to clinch their second-straight NL Central title. Despite trailing 1-0 early, they ended up cruising to a 5-1 win and got to celebrate at Busch Stadium.

Jason Heyward walk-off slam – 6.6.18

After losing the lead in the ninth inning, the Cubs faced a 5-3 deficit going to the bottom of the inning. With Adam Morgan on the mound and Jason Heyward up, the veteran outfielder turned on a 2-2 pitch and blasted a walk-off grand slam to right field.

Alec Mills no-hits the Brewers – 9.13.20

The former college walk-on threw a no-no against the division-rival Brewers at an empty Miller Park. Who would have thought?

And now, time for the number one moment.

Chicago Cubs: There will never be a greater moment for a Cubs fan than the time he/she watched 108 years of suffering get washed away in Cleveland

October 14, 1908, Bennett Park. Detroit, Michigan.

Cubs starting pitcher Orval Overall gets Tigers catcher Boss Schmidt to pop out in foul territory to Cubs backstop Johnny Kling to clinch the 1908 World Series title. The Cubs were back-to-back champions as they defeated the Tigers in five games, sealing the series with a 2-0 win.

108 years (approx. 39,466 days) later.

November 3, 2016 – 12:47 PM (EDT). Progressive Field. Cleveland, Ohio.

Cubs reliever Mike Montgomery gets Indians pinch-hitter Michael Martinez to ground out slowly to Kris Bryant at third, who slings the throw over to Anthony Rizzo to clinch the 2016 World Series title. A century-long drought, a supposed “curse”, gone.

The night fans had dreamt of for such a long time had finally come true when the Cubs beat the Indians 8-7 in 10 innings in Game 7. This was the ultimate goal of the Theo Epstein rebuild, and it was accomplished. This seventh game came after the Cubs were down 3-1 in the series, only having a 7.5% chance of coming back. A close 3-2 win in Game 5 and a 9-3 blowout win in Game 6 set it all up for an epic winner-take-all showdown in Cleveland.

Chicago Cubs: Remembering Game 7

Kyle Hendricks vs. Corey Kluber

Progressive Field was buzzing before the first pitch as one of baseball’s most historic games was about to get underway. While the Indians home field, the crowd was really neutral. Thousands of Cubs fans made their way to Cleveland that night and there were some sections that were more blue than red.

Kluber was tough as nails all postseason, but Dexter Fowler was not going to let the pressure get to him. His leadoff home run to dead-center field pumped up the Cubs and the Cub fans at Progressive Field as he became the first player in MLB history to ever lead off a World Series Game 7 with a home run. After two scoreless innings from Hendricks, the Indians would tie it in the third on an RBI single by Carlos Santana, 1-1 heading to the fourth inning.

The Cubs would finally get the offense going as Addison Russell hit a shallow flyball to center, which ended up scoring Kris Bryant and Willson Contreras followed up with a double off the wall to score Ben Zobrist. In the top of the fifth, Javier Baez hit a solo shot to right center field, chasing Kluber out of the game and forcing the Indians to bring in stud reliever Andrew Miller to limit the damage. With Bryant at first with two outs, Anthony Rizzo doubled into the right field corner to score the fifth run. 5-1 Cubs going to the fifth.

Hendricks, while getting outs, was giving up some hard contact and after a two-out walk Joe Maddon made a controversial move (the first of several) to take The Professor out and bring in starter Jon Lester. With Lester and David Ross in, a single and wild pitch scored two Indians runs and made it a 5-3 game. Lester got out of it with the lead, but the damage was done.

Will Miller still in the game and Ross coming up to bat, the final at bat of his career, the 39-year-old took the All-Star reliever deep for a solo home run to make it 6-3. Now it was Lester’s turn to keep getting outs and preserve the lead for the next two to three innings. The score remained the same until the eighth. With two outs and nobody on…four outs from victory and hard-throwing Aroldis Chapman on the mound, the curse had one more shot at Cubs fan’s hearts. With a run in, and the tying run at the plate, Rajai Davis stepped up.

Everyone remembers what happened. A 6-3 lead turned into a 6-6 tie in the blink of an eye. Davis circling the bases with his tongue out and Cleveland fans going nuts. It felt like the Cubs could very well be denied again. Despite getting the potential go-ahead run to third in the top of the ninth, the Cubs failed to score with Baez bunting foul and Fowler bouncing out to the middle of the diamond. Maddon left the gassed Chapman in to pitch the bottom of the frame and somehow forced extra innings while throwing less than 100 MPH.

Down came the rain, and on came the tarp. Jason Heyward rallied the team together in the weight room at Progressive Field as they waited out the weather. It did not last long, and the game resumed in the 10th inning.

Kyle Schwarber, who tore his knee up in April, singled off Indians reliever Bryan Shaw to lead off the inning. Albert Almora came in to pinch run. Bryant flew out to the warning track, but Almora tagged up and went to second. Rizzo was intentionally walked to face Ben Zobrist. The veteran utility man smashed a rocket past Jose Ramirez down the third baseline to score Almora, as he pumped his fist when he reached second. 7-6 Cubs. Soon after the Cubs would load the bases and Miguel Montero singled to left to make it 8-6. They could have done more damage, but Heyward struck out and Baez flew out. Three more outs to get.

Carl Edwards Jr. came on for the Cubs and quickly got Mike Napoli to strike out and Ramirez to ground out to short. Two outs and nobody on, Brandon Guyer walked, took second, and Davis singled up the middle to make it 8-7. Maddon came out to pull Edwards Jr. to bring in Montgomery to face Martinez.

“Here’s the 0-1. This is going to be a tough play, Bryant, the Cubs…win the World Series! Bryant makes the play! It’s over! And the Cubs have finally won it all, 8-7 in 10.”

The team celebrated on the field and thousands of people took to the streets of Wrigleyville. Fireworks shot off all around Chicago as horns honked, champagne was uncorked and Old Style beer flowed through the mouths of fans. A few days later the city was filled with over five million people for the victory parade, one of the biggest gatherings in human history. I could write a book on that entire run, it was such a great time to be a Cubs fan and I will never forget it.

All good things must come to an end, right? Feels like it should not be coming to an end this fast but it is. Remembering these great moments puts things in perspective. Cubs fans could be lucky to put together a list of Top-10 great moments over a 70-year period from 1946-2014, and even so, they do not come close to some of the moments we had seen over the past six years.

I, like most fans, wanted much more after 2016. The promise of multiple title runs was enticing, to say the least, but it simply did not happen and the league quickly passed the Cubs by. For now, I will remember the good times and hope this next era brings more great memories.