After Cubs trade one-third of their opening-day roster, the offseason will be a true indicator of their retooling status

WASHINGTON — Roughly three hours after the Chicago Cubs concluded dramatically reshaping their roster — and by extension the organization — with their trade-deadline deals, right-hander Jake Arrieta stepped onto the mound at Nationals Park.

The symmetry was fitting: Eight years ago, Arrieta was one of two upside players the Cubs acquired in a July trade as the organization, early in the Theo Epstein-Jed Hoyer regime, targeted younger talent and assets in their rebuilding effort. Five playoff appearances, three division titles and a World Series championship later, Hoyer is tasked with overhauling the roster and retooling the Cubs into another consistent postseason presence in his first year as president of baseball operations.

The revamped Cubs tried to move forward Friday. It was not an easy task on an emotional day that ended in a 4-3 loss for a team that saw eight players depart this week in seven trades, three of which featured franchise icons Anthony Rizzo, Kris Bryant and Javier Báez. The carnage:

— The Cubs on Monday sent reliever Andrew Chafin to the Oakland Athletics for two minor league prospects: Triple-A outfielder Greg Deichmann and low-A right-handed starting pitcher Daniel Palencia.

— Reliever Ryan Tepera was traded to the Chicago White Sox on Thursday for minor league pitcher Bailey Horn.

— Rizzo, one of the cornerstones of the Epstein-Hoyer rebuild, was dealt to the New York Yankees on Thursday for minor league right-hander Alexander Vizcaíno and minor league outfielder Kevin Alcántara.

— The Cubs traded closer Craig Kimbrel to the White Sox on Friday for second baseman Nick Madrigal and reliever Codi Heuer.

— Shortstop Báez and right-hander Trevor Williams on Friday went to the New York Mets in exchange for outfield prospect Pete Crow-Armstrong.

— Bryant, the 2015 NL Rookie of the Year and 2016 NL MVP, was traded to the San Francisco Giants on Friday. The Cubs received a pair of prospects in return: right-hander Caleb Kilian and outfielder Alexander Canario.

— The Cubs on Friday sent outfielder Jake Marisnick to the San Diego Padres for minor league right-hander Anderson Espinoza.

Cubs manager David Ross described Friday as sad, emotional, difficult — “a lot of negative words that I usually don’t like to use.”

“They get a chance to go to some teams that are in the hunt and chasing championships,” Ross said. “I’m happy for them. But outside of the manager side, I feel like I’m losing some friends for a minute and I think that’s difficult for me personally.”

But there still was a game to be played so, around 5:15 p.m. ET, the Cubs began infield work. The sight was slightly jarring: Patrick Wisdom manning first base, David Bote and Sergio Alcantara at second and shortstop, respectively, with Matt Duffy at third. The Cubs’ new reality will create further scrutiny in the coming months following Hoyer and the front office’s commitment to trading the organization’s best players. One-third of the Cubs’ opening-day roster is gone. In return, the Cubs acquired 11 players, including nine prospects.

“The decisions that we have to make in this game sometimes are really difficult,” Hoyer said Friday, “and I hope that people don’t ever think that there’s not a real emotion that goes into doing that.

“When you make all these different bets on prospects, you know that you’re not going to hit on every one, but it’s certainly our hope, and it was our hope last time.”

Once they lost 11 straight games in late June into July, combined with the Milwaukee Brewers taking off with an uncatchable lead in the division and the National League wild card not a realistic shot because of the stacked NL West, “we got to a place where it was, at least to me, a very clear and obvious decision,” Hoyer said of the Cubs going all-in as sellers.

Hoyer, speaking for nearly 30 minutes after Friday afternoon’s trade deadline passed, believes the Cubs sped up their efforts to retool with the trades. He pointed to the Detroit Tigers, San Francisco Giants and Philadelphia Phillies as examples of teams with a stretch of good postseason runs, but when they got to the end of that cycle prolonged playoff droughts because those organizations “basically ran to the end of the cliff and they fell off and they had to rebuild.” The Giants haven’t appeared in the playoffs since 2016, while the Tigers’ postseason-less stretch began in 2015 and the Phillies own the second-longest streak, their last playoff game coming in 2011.

“We were willing to go to that point, if this was a winning team this year, but we weren’t,” Hoyer said. “So with that, we were able to, in my mind, speed that process up dramatically because we’re able to acquire a lot of young talent, some on the major league team, some that’ll be in the minors.

“We did everything we could today and over the last week to try to reset this organization and to try to make the best decisions possible.”

Nothing is preventing the Cubs from negotiating with soon-to-be free agents Rizzo, Bryant and Báez in the offseason, and the door isn’t closed on a potential return, Hoyer noted. But for any Cubs fans dreaming of the team reuniting with any of the now-former stars in free agency, the trio and organization had months to reach agreements on contract extensions. Yet they didn’t. Now the Cubs possess both prospect and financial capital to enact whatever approach Hoyer ultimately takes in building the next contender.

“We made offers to everyone that I believe will hold up exceptionally well and we weren’t able to reach deals,” Hoyer said. “Does that frustrate me? It does. I know we put our best foot forward and I’m proud of the offers we made.”

Hoyer has through the end of the offseason to prove the Cubs are indeed retooling and not doing some form of a rebuild. The trades made this week need to be viewed with that aspect and big picture in mind. Hoyer took a logical approach in cashing in two more months of Rizzo, Bryant and Báez, even though it forced Cubs fans to endure a painful 48-hour teardown. Strengthening a farm system that once was a valuable source of talent and trade commodities during the Cubs’ successful run the previous five years is part of the equation behind these moves. The Cubs don’t win the World Series in 2016 without them.

“We have raised the expectations of what people want in this city,” Hoyer said. “Cubs fans don’t expect to make the playoffs every 13 years like they did before. They expect to be in the playoffs, they expect to win. And I’m super proud that we created that, we caused that expectation. And now we have to live up to that expectation, and that’s fantastic.

“I don’t care about trying to look like you’re competing or finishing in second place. I care about trying to win championships.”

Hoyer doesn’t know what path the Cubs will take in the offseason in his quest to build their next World Series title contender. He will need to back up his assertion, through whatever direction they go, that the Cubs won’t be enduring another painful rebuild. Words only go so far. Action matters. The Cubs have only $44 million guaranteed currently on next year’s payroll. They should have the financial means to sign impactful talent in free agency. The offense is lacking star power after this week’s moves, and there are plenty of questions surrounding the pitching staff and who they can count on in 2022 and beyond.

Hoyer deserves an opportunity to put his mark on the team now that he’s running the show in baseball operations. With it comes added scrutiny, in both a short- and long-term lens for the seven trades and the 11 players the Cubs acquired this week.

“I don’t know where we’re going to go (in the offseason), but I promise you, the entire focus is going to be on ‘How do we figure out how we get to a place to have the next great Cubs team?’ ” Hoyer said. “Because people expect deep postseason runs. People here haven’t been satisfied with early exits or wild cards — and that’s awesome — and so that’s what we need to provide the fans.”