From a team and off-the-field perspective, Montgomery will always carry the fondest memories and is sad to go. From an individual standpoint, he's excited to move and and get the chance to be a full-time starting pitcher.
"It's been a great run for me here in Chicago over the last three-and-a-half years," Montgomery said in an interview on the McNeil & Parkins Show on 670 The Score. "It's been unbelievable, and I had a son born here three months ago. There was the World Series. It's been a journey, for sure. It's come to an end. Obviously, it didn't work out ideally the last couple months but a lot more good times than struggles for me. And I grew up a lot as a player and a person here. I've learned a lot, especially in the last couple of months. I've really just learned a lot about myself. From a pitching standpoint, I feel good. I feel healthy, and I'm excited to get a new opportunity. I wish everybody here the best. The team has a lot of great expectations and a lot of great players to match that and unfortunately, my time here is done. But I'll be rooting those guys on. I wish them all the best."
Montgomery, 30, had long expressed his desire to the Cubs to be a full-time starter, but that role wasn't available in Chicago. He started 38 games for the Cubs in the previous three years, including 19 in 2018, but all 20 of his appearances had been in relief this season as the Cubs' rotation was set. Montgomery had struggled, posting a 5.67 ERA and 1.78 WHIP.
Asked if he formally requested a trade in conversations with Cubs management, Montgomery indicated it was a complicated situation.
"It wasn't a straight 'trade me,'" Montgomery said. "There's a lot of layers to it and a lot of moving parts. It was one of those situations where I see myself as a starter and they were kind of trying to fit me into the mold of a late-inning reliever. Look, I still think pitching is pitching. It's kind of tricky. I just didn't feel like I had consistent opportunities. I've been in the bullpen in the past. I grew up as a starter. I've always been a starter. It's where I feel like I fit best and provide the most value to a team. Being able to go back and forth the last few years has taught me a lot. I think it was time to just get a new opportunity. I'm so thankful for Kansas City giving me that shot. But being here in Chicago has been an unbelievable ride.
"There's so many good memories here. It's tough leaving. I'm definitely am going to feel some emotion leaving, and I have walking out today and getting my stuff. There's definitely emotions there. I think it was a good run. I think hey, it was just time for me to go. I think it's going to work out for everybody."
"It definitely was a life-changing moment," Montgomery said of that final out for the championship.