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

CLEVELAND, OH - NOVEMBER 02: The Chicago Cubs celebrate after defeating the Cleveland Indians 8-7 in Game Seven of the 2016 World Series at Progressive Field on November 2, 2016 in Cleveland, Ohio. The Cubs win their first World Series in 108 years. (Photo by Elsa/Getty Images)
CLEVELAND, OH - NOVEMBER 02: The Chicago Cubs celebrate after defeating the Cleveland Indians 8-7 in Game Seven of the 2016 World Series at Progressive Field on November 2, 2016 in Cleveland, Ohio. The Cubs win their first World Series in 108 years. (Photo by Elsa/Getty Images) /
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Anthony Rizzo / Chicago Cubs
(Photo by Ezra Shaw/Getty Images) /

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.

Next. Ranking the 25 best players in Chicago Cubs history. dark

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.