Cubs' Mike Montgomery had the all-time moment in 2016. After that? Baseball wasn't easy

Mike Montgomery got the call. Then he got the ground ball.

A man could live 1,000 baseball lives and never come through in a bigger moment than two outs in the 10th inning of Game 7 of the 2016 World Series in Cleveland.

Throughout Cubdom, Montgomery’s one-out save — the first of his professional career — will live forever. Ten years since Nov. 2, 2016, the 37-year-old still can close his eyes and feel the rush of it.

“The highest high imaginable,” he says.

How many pitchers can say they got a final out that endures as toweringly as that one? But baseball isn’t a storybook, and Montgomery had to fight with all his might for every inch of success in the game after the night to end all nights. A former Royals first-round pick who threw back-to-back shutouts in his first month in the majors with the Mariners in 2015, Montgomery still believed after being traded to the Cubs in July of 2016 that he could become “one of the best players ever in the game.” Needless to say, that didn’t happen.

Instead, a lefty whom Kyle Hendricks predicted the following spring would become the Cubs’ next pitching star lasted another two-plus seasons on the North Side — never truly locking down a rotation spot — and was dealt in 2019 back to the Royals, with whom he fizzled out. From there, it was an odyssey: Montgomery was released in spring training by the Mets, bombed out in the minors with the Yankees, had an unsuccessful stint in Korea, gave it another go with the Mets in Triple-A but got shelled, signed with a Mexican League team but was soon released, pitched forgettably in the Dodgers’ system and in 2024 — making less than $3,000 a month in one last gasp — turned out to be just another arm for the Long Island Ducks of the independent Atlantic League.

It was over.

No more storybook moments. No more dream.

Fortunately, no regrets the size of which keep a man up at night.

“I’ve been in the highest of highs and then been in Mexico sitting there sick from the water, thinking, ‘What am I doing? I’ve got a two-year-old and a daughter about to be born.’ In Long Island, here I am a World Series champ with six years in the big leagues. I was throwing 90, 92, thought my stuff was good enough, but nobody called. …

“But I’ve talked with some close friends and my wife about this: What if I would’ve had a 12-year career and made hundreds of millions but never won anything? To be a part of one of the best moments in baseball history, I don’t think there’s enough money for that. I wouldn’t trade it for anything. It’s not like we’re broke. I could’ve had a better career, made more, but I had the kind of pinnacle moment that I can take with me forever.”

Since May, Montgomery, who lives in Scottsdale, Arizona, with his family, has been the rehab pitching coach for the Mariners, a job he’s enjoying. Son Max and daughter Zoe are growing. Life is good. Any regrets are small enough.

Courtesy of Mike Montgomery

“The last few years of my career, I battled with being kind of angry, with, ‘I’m not where I want to be considering I’ve already been to the top of the mountain,’ ” he says. “I’ve had to work through that, but I’m at peace with it. I’m very proud of my career. Man, I wish I could have been a 10-, 15-year player, All-Star games, all that. I may not have been the best player to ever play, but I have been to the best moment in baseball history.”

Among his worst moments: being ejected from a 2021 game in Korea with the Samsung Lions, and suspended for three weeks, having gone after a “disrespectful” umpire and needed to be held back by several teammates before pelting the ump with a rosin bag.

Nobody’s perfect.

Montgomery was far from perfect after going from Seattle’s rotation to the Cubs’ bullpen just before the 2016 trade deadline. He met the Cubs in Milwaukee, where he gave up a homer in his first appearance. In his next appearance, he got walked off by the White Sox. By the time he got to his locker at Wrigley Field for the first time, a letter from a “fan” was waiting for him.

“You’re the worst player ever. You must be pitching with the wrong arm,” Montgomery remembers it saying.

Not long after the final out in Cleveland, Montgomery actually wrote that person back — the only fan letter he ever returned. The message spanned all of seven words:

“I hope you enjoyed the World Series.”

Signed, Mike Montgomery.

That, too, would be mighty damn hard for anyone to top.