Now happy with the Giants, Kris Bryant has no regrets about how his Cubs career ended

SAN FRANCISCO, CALIFORNIA - AUGUST 01: Kris Bryant #23 of the San Francisco Giants takes fielding practice before the game against the Houston Astros at Oracle Park on August 01, 2021 in San Francisco, California. Bryant was acquired by the Giants in a trade with the Chicago Cubs on July 30. (Photo by Lachlan Cunningham/Getty Images)
By Jon Greenberg
Aug 6, 2021

MILWAUKEE — It was about 10 minutes until the trade deadline and Kris Bryant was confused.

“I heard some rumblings, but it’s like, man, after three years of answering all the questions about being traded and stuff, and I’m not going to be the one who is traded? How did that work out?” he said Friday afternoon.

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It was his wife, Jessica, who first broke the news to him. And just as he was talking to her, Giants GM Scott Harris was calling him.

In that viral video you saw, he was talking to Cubs president Jed Hoyer, but he already knew he was heading to San Francisco. It was Anthony Iapoce, the Cubs’ hitting coach, who made him tear up.

“He’s crying, like ‘Everybody’s going away,’” Bryant said. “That got to me.”

Five games into Bryant’s second life as a professional baseball player, he’s nothing but smiles. The weight is off his shoulders. After years of rumors, it finally happened. And it has worked out great for him so far. The first-place Giants have won four of five games since he reported to San Francisco. He homered in his debut, and he led the Giants to a wild comeback win to close out their series in Arizona.

Bryant said he hasn’t connected with Anthony Rizzo and Javy Báez about how they all homered in their first games, but yes, he thought it was cool, and he understands how the fan base saw it.

“What a coincidence for all that to happen and just pouring salt on a wound, kind of,” he said.

Indeed.

All three players are with teams in the playoff chase and that could conceivably give them a long-term home.

“I think there was a little bit of ‘let’s get these guys somewhere they deserve to be and want to be,’ and I appreciated that,” Bryant said.

Where Bryant belongs is with the Cubs, the team that drafted him and made him the centerpiece of their rebuild. Scott Boras aside, and I know that’s easy for me to say, the Cubs should’ve signed him to an extension, found some kind of common ground even if they had to overpay him. Letting Bryant leave before he retired might make fiscal sense, but it doesn’t make baseball sense.

What that in mind, what did Bryant think about Hoyer’s strong language in his ESPN 1000 interview, in which he essentially pinned the lack of contract extensions on the players?

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“It’s tough because I always wanted to take the high road,” Bryant said. “And I’ve never been about calling out people who’ve done special things for me in my career. And regardless of the negatives, or anything that has surrounded me or the situation there, I always think back to my time there and feel happy about it and have great memories about it. And, you know, I have praise for Jed and Theo (Epstein), and there’s a lot of stuff that I went through and stuff that necessarily I didn’t agree with all the time, but they gave me an opportunity to wear the pinstripes and play for such a historic organization and win there, and I’m always going to let that overshadow any negative things that are out there.”

Bryant was asked if Hoyer was wrong in his assessment that his “Big Three” didn’t want to sign extensions.

“Well, in his mind, he’s going to be right, and then maybe in ours, he will be wrong,” Bryant said. “And it’s OK to disagree and then you just move on from there.”

While it doesn’t mean there weren’t more front-office conversations with Boras, Bryant said the only time he was personally approached by the front office about signing an extension was during spring training in 2017.

“I kind of felt like it was always out there, like, ‘Hey, we’re constantly trying to get an extension done’ and stuff like that,” he said. “And in reality that didn’t happen. There were conversations after 2016 and then after that, it was like, nothing. I was always open to hearing, and I’ve always said that. But there was just wasn’t anything after that.”

The early success of the Cubs and their young players was certainly an impediment to getting them to sign a team-friendly extension. The Cubs got Rizzo to do it early in 2013, when he was on one of the worst teams in baseball. The White Sox inked many of their young players to long-term deals before they even came up to the majors.

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It was different on the North Side.

“At the end of the day, like Jed said, he puts his head on the pillow at night and, you know, I know that I gave it my all and I was always willing to listen to anything,” Bryant said. “And at the end of the day, we had conversations after 2016 and that was it. So that’s just where I’m at. And like I keep saying, there’s no hard feelings. I’ve had great, unbelievable memories there. And, you know, just I look back and it’s like it’s some of the happiest moments of my life, and nothing can change that.”

Bryant wishes the contract talk wasn’t overwhelming the narrative around him the past few years.

“Sometimes it would honestly be easier if there were no extension talks or any of that,” he said. “It’s just like, OK, you’re here, you’re here for seven years in my case, and you’re gone or you’re here.”

The way Bryant sees it, the Cubs front office shouldn’t live with any regret either.

“I know that that has been a big story, but it really shouldn’t be the story,” he said. “The story should be what we accomplished there and just the good things that we’ve done there, and the good people that they signed and how they’ve grown into winners. And now they can look back and see me here, see Javy, Craig (Kimbrel) and Rizz and be proud of the players that we are because they’ve had a big impact and making us who we are.”

Maybe that goes for Cubs fans too, at least the ones who are still angry about the end of this era.

It was here in Milwaukee where the Cubs’ season fell apart, which led to the window closing. On June 28, it was a tie score going into the bottom of the eighth when the Cubs gave up 10 runs to lose 14-4. The next day they lost 2-1, and the day after that, after scoring seven runs in the first inning, the Cubs lost 15-7. They came into the series down three games to Milwaukee in the NL Central and left with a six-game deficit. By the time they lost their 11th game in a row, they were down nine games and the sell-off was imminent.

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“Things just kind of unraveled quickly, and sometimes that happens and the perfect storm of everything,” Bryant said. “And everyone is gone.”

Now, on his second road trip with the Giants, Bryant was in the home clubhouse and the TV was on. The White Sox were playing the Cubs at Wrigley Field, and he wasn’t there.

“It’s weird sitting here on a Friday and watching the Cubs game on TV at 1:20,” he said. “We would always talk about that there. On Friday, you take pride you’re the only team playing at that time and everybody is watching you. It’s true. It’s on in the clubhouse and it’s kind of funny to watch. I’m looking at the lineup and trying to figure out who’s who and stuff like that. But seeing them on TV is kind of surreal.”

Bryant said he’s open to talking to the Cubs about a new contract this offseason, and Hoyer told him he is as well, but everyone knows that a new deal is unlikely. Bryant will get a handsome contract this winter, possibly from San Francisco, which seems like a perfect long-term fit.

He joked about wanting a throne and a red carpet for his return to Wrigley Field on Sept. 10, but really he just wants to be remembered there as someone who ran hard down the line, did what he could and, most importantly, as someone who helped lead the Cubs to what they’ve wanted since 1908.

The Cubs’ tanking in 2012 led to Bryant’s drafting in 2013. It was inarguably the most important juncture of the last rebuild. If the Houston Astros had drafted Bryant instead of Mark Appel, we’d still be talking about the Cubs’ drought. Bryant was the Rookie of the Year when the Cubs arrived in 2015 and the MVP when they won it all. I joked with him about getting his number on a flag, and maybe it happens one day.

But seven years is a long time. Bryant said he can’t put his finger on why the Cubs didn’t win another World Series because he knows, from the inside, how hard this game really is. Since the Giants won their third World Series in five seasons in 2014, six teams have won a championship. Maybe that’s how it should be.

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“It would be great for a fan base to say, ‘Hey, we won five World Series in a row.’ Is that good for the sport?” Bryant said. “Who knows?”

While we call the Cubs the “’85 Bears” as a pejorative, it’s not like Chicago doesn’t cherish that team. The same will be said of the 2016 Cubs in the decades that follow.

“I think we’ll look at that era like that’s one of the more dominant eras of baseball, and I feel really proud of that,” he said.

Any regrets? Bryant said he probably showed up too early sometimes, unlike more laid-back teammates like Rizzo. He said he loved living in Wrigleyville with his family this year, after six years of living downtown, and he wishes he would’ve made that move earlier.

As his time wound down at Wrigley Field, Bryant played a lot in the outfield, which showed his versatility. But it also allowed him to interact with Cubs fans, who let him know they wanted him to stay. They extended their love to him in those games, and there’s no arguing that fact.

“Yeah, it was really cool,” he said. “It was nice to hear them compliment me, and I gave it back a little, too. I’m not super playful out there in the outfield. But you know, when they’re just all over me the whole game telling me how much they love me, I’ve got to show some love back, because they’ve done some great things for me and my family.”

(Photo: Lachlan Cunningham / Getty Images)

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Jon Greenberg

Jon Greenberg is a columnist for The Athletic based in Chicago. He was also the founding editor of The Athletic. Before that, he was a columnist for ESPN and the executive editor of Team Marketing Report. Follow Jon on Twitter @jon_greenberg