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Underdog: Mike Montgomery threw the greatest pitch in Cubs history

A solid but unheralded acquisition that July, Mike Montgomery became the hero Chicago needed.

World Series - Chicago Cubs v Cleveland Indians - Game Seven
Mike Montgomery picked a hell of a night for his first career save.
Photo by Elsa/Getty Images

By the time Mike Montgomery entered Game 7 of the World Series, I was in agony. And not the semi-fun baseballish “can you believe how tense this meaningless game played by strangers is making me feel” kind. Legit “five decades from now, a mortician will examine my body and ask, ‘What the hell happened on November 2, 2016?’” agony.

As Montgomery trotted in from the Jacobs Field (#NeverFlo) bullpen with two outs, one Cleveland run already scored, and freshly minted foulest villain in human history Rajai Davis on first representing the tying run, I was barely hanging on to any vestiges of emotional stability, begging the TV, “Just... get... the third out!”

My ultimate dream as a baseball fan... the “what if” I had imagined a seemingly infinite number of times since I had fallen hard for the Chicago Cubs as a child... was one more out away. And never in my 37 years on this planet had it felt so distant.

At the time when they needed the gutsiest pitching performance in the history of the franchise, the Cubs were turning to a second year curveball specialist who topped out at 93 MPH. It felt like in his greatest hour of need, Joe Maddon had decided to signal for MLB The Show Create-A-Player.


When the Cubs acquired Montgomery on July 20th of that year, I didn’t know much about him. In fact, I initially got him confused with another relief pitcher named Mike MacDougal because my brain sometimes factors similarity scores based solely on alliteration. MLB trade experts analyzed the deal and seemed to agree that Montgomery was left handed. He had some good numbers and felt like the very definition of an anonymous bullpen depth piece.

World Series - Chicago Cubs v Cleveland Indians - Game Seven
Mike Montgomery, about to change all of our lives for the better.
Photo by Jason Miller/Getty Images

At the time of the trade, Cubs President of Baseball Operations Theo Epstein had this to say about his new southpaw:

“If we hit on this deal and Montgomery becomes someone who can help us now as we head down the stretch and help us later, we’ll be very happy with this transaction.”

It’s nice to know that if Theo ever gets tired of baseball, he can pick up a fallback career in dramatic foreshadowing.

Five days later, the Cubs made a much more celebrated trade, acquiring flamethrowing closer Aroldis Chapman. As a relief pitcher, he was dominant. As a human being, he was horrific, having served a 30 game suspension for domestic violence that spring. My friends and I dreaded the likely thought that if the Cubs were to make our dreams a reality, it would come with Chapman on the mound.


Flash forward back to Game 7 and an exhausted Chapman had blown a 6-3 lead with four outs to go and given up one of the most infamous game-tying home runs in baseball history to a player who had hit only 57 career homers previously. Karma picked a hell of a time to exist.

You know the story from there. The Cubs left the go ahead run at third in the ninth. Rain delay. Jason Heyward speech. Ben Zobrist clutchest RBI double ever. Anthony Rizzo hands on head screaming. Miguel Montero insurance run RBI. Two quick outs in the bottom of the 10th. And then a walk, stolen base, and RBI single made it a one run game that would... not... end. The Cubs needed someone... anyone... to finish the job.

Enter the anonymous bullpen depth piece. When he arrived at the mound, Montgomery was already spent, having warmed up four times previously that night. Plus, he hadn’t thrown a single curveball for a strike in the bullpen. He asked Montero how they were going to attack Cleveland’s Michael Martinez. Montero’s response: “I don’t know, dude. Let me think about it.”

I will see the following sequence every day for the rest of my life: first pitch curve ball strike. Second pitch curve ball chopped weakly to third. Joe Buck proclaims, “This is gonna be a tough play... Bryant... THE CUBS...” And by the time he adds, “WIN THE WORLD SERIES,” I am in an ecstasy that I didn’t know existed anywhere in the universe until that moment.

The Cubs did win a championship thanks to the trade they made that July. It just wasn’t the one they assumed it would be. From that night forward—and for the rest of his life — Mike Montgomery was promoted to Create-A-World-Series-Hero.