Once a top Royals prospect, Mike Montgomery finds home in Cubs’ bullpen

For the last two seasons, Mike Montgomery watched nearly every pitch of the World Series. Maybe he would have done this anyway, he says. He’s always been a baseball junkie. But in this case, as he lounged on a couch and sat in front of the television, the viewing experience was deeply personal. He couldn’t take his eyes off the screen.

The Kansas City Royals were his first club, the organization that drafted him, nurtured him and offered him a career. As he watched during the last two Octobers, this strange feeling kept surfacing.

“I kind of felt the feeling of ‘What if?’” Montgomery says. “I could have been there. I should have been there — if I’d have done this differently or if I’d have just took this person’s advice.”

As Montgomery tracked those postseason runs, he thought about the long bus rides with Eric Hosmer and Mike Moustakas. He thought about the minor-league championships they won together. He thought about the hype — the Sports Illustrated article, the Baseball America covers, the hope that had coalesced around a group of young players.

Five years ago, Montgomery was one of baseball’s top pitching prospects, a jewel of one of the best minor-league systems in history, a future starter in the Royals rotation. And then, suddenly, he wasn’t. He hit a wall in the minor leagues. He was traded. He watched the Royals end a 29-year playoff drought and end up in the World Series. And in some ways, it was kind of a bummer. That was supposed to be him there, too.

But something strange happened last October, as he watched his old teammates finish a championship against the New York Mets. Above all, Montgomery says, he felt good for his friends. And he felt a sudden surge of confidence.

“It kind of gave me a sense of, ‘I’m gonna do it, too,’” Montgomery says. “I’m going to get to a World Series and win a World Series. Because I played with them. I played with that whole team. They can do it. So why not me?”

At this point, Montgomery points out that he did not expect this to happen so fast. One year later, he is at Progressive Field, entering his first World Series, as a left-handed member of the Cubs’ bullpen. As the Cubs opened the series against the Cleveland Indians on Tuesday night, Montgomery occupied space in the Chicago relief corps next to Aroldis Chapman and Hector Rondon. No, he could he not have predicted this.

“A crazy ride,” Montgomery says.

After beginning the season with the Seattle Mariners, Montgomery was acquired by the Cubs in a July trade. He joined the club’s bullpen and posted a 2.82 ERA in 38  1/3 innings. In the postseason, he has allowed four earned runs in 9  2/3 innings. At times, Montgomery says, it’s been hard to internalize the experience, to understand how he ended up here, in the middle of the Cubs’ first World Series appearance in 71 years.

“I’m not going to lie,” Montgomery says. “When I got over here, I didn’t realize the magnitude of this team.”

The Cubs targeted Montgomery to be an extra left-handed arm during the stretch run. Montgomery is hoping to oblige — and maybe be a little more. He is 27 years old now, years removed from top-prospect status. But he still believes in his ability to get major-league hitters out.

“I know that, if I’m at my best, both physically and mentally, I can be a very solid major-league pitcher,” says Montgomery, the No. 36 overall pick in the 2008 draft.

And yet, the road to here has been circuitous. In 2011, Montgomery was rated as Baseball America’s 19th best prospect after a dominating turn at Class A Wilmington and Class AA Northwest Arkansas. The Royals envisioned him as a piece for the future. He arrived at Class AAA Omaha the next season as a “cocky” 21-year-old. That’s his word.

“I didn’t know how to fail,” says Montgomery, a native of Santa Clarita, Calif. “Being that young, I had to understand that this game is a game of failure and a game of constant improvement, and I think I might have got a little complacent and a little cocky. (It was like) ‘OK, I’m 21 at Triple-A; I’m gonna be a dominant big-leaguer.’ But I didn’t realize the little things that you had to do to be that.”

Montgomery struggled in 2011 and 2012, posting an ERA above 5.00 each season. After the 2012 season, as his stock diminished, he was packaged in a deal with Wil Myers, Jake Odorizzi and Patrick Leonard to Tampa Bay for James Shields and Wade Davis. The deal set the stage for two World Series appearances in Kansas City. Montgomery continued to toil in the minor leagues.

After three seasons in the Rays organization, he was sent to the Mariners for pitcher Erasmo Ramirez before the 2015 season. Montgomery notched a 4.50 ERA in 16 starts last year before flashing promise — and increased velocity — out of the bullpen this season. On July 20, he was traded for a third time, sent to Chicago in a deal that included Cubs hitting prospect Dan Vogelbach.

On the day before the World Series, Montgomery pointed to a list of factors for the improved performance. He’s shored up his mechanics, becoming more consistent in his lower half. He’s worked on controlling his breathing patterns on the mound. The Cubs’ staff has worked with him on pitch sequencing.

But he also lists one appearance — a start — as a pivot point. On July 10, when he was still with the Mariners, Montgomery made his first start at Kauffman Stadium, allowing one run in 6  1/3 innings in an 8-5 victory. These days, Montgomery says he still holds fond feelings for the Royals organization, likening it to an alma mater. And in some ways, on that day, it felt like he had come full circle.

“It was kind of like that rewarding experience,” Montgomery says. “I finally made it to Kauffman Stadium.”

This story was originally published October 25, 2016 at 4:43 PM with the headline "Once a top Royals prospect, Mike Montgomery finds home in Cubs’ bullpen."