CHICAGO -- Last Tuesday, at the brink of MLB's trade deadline, Chicago Cubs president of baseball operations Jed Hoyer had a decision to make: Trade catcher Willson Contreras for what he believed was below market value, or keep him and potentially get an extra draft pick if Contreras leaves as a free agent at the end of the season.
For weeks, it had been a fait accompli that Contreras would be moved, especially after Hoyer had pulled off another deadline dump one year earlier with stars Anthony Rizzo, Kris Bryant and Javy Baez. The Cubs are rebuilding and focusing on youth, so getting another prospect or two in exchange for a few months of Contreras' service was attractive to Hoyer and his front office.
There were conversations, of course, with Cleveland and Tampa Bay, both organizations that have a need at catcher but are usually loath to give up prospects with team control. The Mets were involved early but never moved, perhaps feeling burned by trading for Baez while giving up rising prospect Pete Crow-Armstrong the year before. The San Diego Padres were also in the mix but fell out once they traded for Juan Soto earlier in the day. The 6 p.m. ET deadline hit, and a deal had never materialized.
"Each offseason and trade deadline, you try to make the right decisions in the moment," Hoyer said this week. "I think we've done a good job of doing that, but you can't force your way in one direction or another. If a trade doesn't line up, you can't force it. You have to realize there may be another option the Cubs can benefit from."
History and reputation allow Hoyer the benefit of the doubt. One current GM described the Cubs as "fair, direct and transparent" when it comes to making trades. And it's not as though Hoyer sat idle -- despite the non-trade of Contreras, the Cubs still made several deals as Mychal Givens, David Robertson, Chris Martin and Scott Effross all changed teams.
The deals made this the second consecutive year Chicago has subtracted instead of added at the trade deadline. It's an unusual position for one of baseball's marquee clubs, even one undergoing their second rebuild in a decade. But their 45-65 record tells the story of this season.
"If everything had gone right and we hit the 90th percentile on certain things, maybe we could have gotten to that point [of adding]," Hoyer said. "But the margin for error was small and being in the position that we are, we should have sold. I don't enjoy the process of selling. I want to flip that to the buy side as soon as possible."
The Cubs are one of baseball's most storied franchises. They're often featured on the national scene -- like in this year's Field of Dreams game against the Reds on Thursday -- and will play the Cardinals in London next season.
All of those opportunities come in part because they're also one of the sport's most beloved. This year, the Cubs have the highest per-game regular-season attendance at 32,873 of any losing team in baseball. It ranks seventh among all teams.
Cubs games are apparently must watch in Chicago, even if their product is unwatchable many nights. Now Hoyer and the rest of the team just have to find a way to change that.
"It's a fan base that deserves a winner because they do show up," shortstop Nico Hoerner said. "They take the time and effort to support us here and even in spring training, when 16,000 come to games. They deserve a winner."
Team owner Tom Ricketts expressed similar sentiments in a statement to ESPN.
"I'll be the first to acknowledge this is not the type of baseball Cubs fans deserve," Ricketts said. "Our decision last year to move away from Cubs players who brought us a World Series title was tough, but we have a plan to return to championship contention by building the next great Cubs team around a young core of players augmented by free agent signings -- and we're making progress."
Ricketts has kept a low profile while Hoyer has gone about the work of building a contender again from the ground up, an undertaking that cites several factors as causes. Over the past decade, the Cubs drafted and developed hitters well, though they failed to do so with pitchers -- save Dylan Cease, whom they traded to the White Sox in 2017, and Paul Blackburn, who netted them Mike Montgomery in July 2016. Montgomery ended up saving Game 7 of the World Series a few months later.
But unlike what the Washington Nationals just did with Soto, the Cubs didn't move any of those homegrown stars at the peak of their value. Those hitters won them a World Series -- but by the time Chicago traded Rizzo, Baez and Bryant last year, the returns were enough to improve their farm system, not remake it with the next Bryant-in-waiting.
So last year, without a pipeline of major-league-ready pitchers and prepared to watch their veteran position players move on, the Cubs believed they had no choice but to start over.
Hoyer is trying to do it differently this time. The Cubs are starting to develop pitchers, beginning with starters Justin Steele and Keegan Thompson. Both have established themselves at the major league level this year, as have position players Hoerner and Christopher Morel and some other pieces. And there are more arms on the farm.
"The goal has been to add as much pitching as we possibly can," Hoyer said. "I look back on when we built up the first time, we had position players lined up, but we never got to the point of having pitchers lined up at every level."
ESPN prospect guru Kiley McDaniel has the Cubs 18th in his latest rankings of MLB farm systems, while Ricketts pointed out FanGraphs has them at No. 4. The team has young players in the low minors with upside, but they still lack a top-25 prospect to raise them any farther up the ranks (part of the reason behind the disparity between the two outlets).
Hoyer also knows that the lack of star power at the top is a problem.
"In 2014, we may have had three to four guys in the top 10," Hoyer said when asked how this season compares to that of 2014, when the Cubs were starting to get competitive. "We had a whole team of prospects on the field at the beginning of 2015. This is less so [now]. But that is what we're building toward. My vision is the same. We're not quite as far along as we were at the end of 2014."
In fact, this Cubs team may be closer to the team that lost 96 games in 2013. It's exactly what they're on pace for this season. But expectations are higher for Cubs fans these days. Winning a World Series in 2016 for the first time in 108 years has raised the bar in Chicago.
And with higher expectations comes more pressure, especially for a bigger market like Chicago.
The difference between the Cubs and smaller-market teams should be that they don't have to dump at the trade deadline more than a couple times to build up their team. Instead of getting rid of players for prospects every year for a half-decade, they can augment their rebuild by spending money. The Cubs' signings last winter of right fielder Seiya Suzuki for $85 million and pitcher Marcus Stroman for $71 million along with smaller signings, like Wade Miley ($10 million), Yan Gomes ($13 million) and Drew Smyly ($4.25 million), should calm some alarmists that they are playing it cheap. The team promises more to come.
"When we build this and get to the point that we've built something special, I know the money is going to be there," Hoyer said. "We want to be strategic and make good decisions with how we spend that money. I feel good about the money we spent on Stroman and Suzuki."
Ricketts added, in his statement: "Our moves over the past year and at the trade deadline have put us in a position of strength in both player and financial currency. We plan to be very active again this offseason competing in the free agent market."
But as Hoyer himself has pointed out many times since starting over, there is no fool-proof path back to contention. Adding a whole team of veteran stars might work for a year or two but almost by definition -- free agents come at an older age -- there is no sustainability to that strategy.
Still, perhaps one of Trea Turner or Carlos Correa or Aaron Judge will make his way to the North Side in 2023. Because unless Shoeless Joe Jackson walks out of the cornfields to play left field on Thursday night, the Cubs are going to have to keep searching for future All-Star or MVP candidates. Injuries at the minor league level have slowed some promising players down, but hitting the free agent market is still their best bet to satisfy that search.
"We have to reconfigure our offense," Hoyer said. "We don't have enough power right now. We have to get the ball in the air. Those are things we'll be focused on this winter."
Ian Happ, the Cubs' player rep and a free agent in 2024, added: "Every player wants to see money being spent across the board. There is some really good talent out there this offseason. There are going to be teams that go out and spend. I think the Cubs will probably be one of those, but only time will tell."
If they don't, a revolt might be at hand. Then again, the tickets keep getting sold -- in Iowa, at Wrigley and likely in England soon. It's no more obvious than in an example like this: On a Tuesday night a week from the deadline, more than 37,000 fans -- fewer than 5,000 short of a sellout -- showed up to Wrigley Field to see the last-place Nationals, without Soto, take on the Cubs.
The fans are there, still willing to pay high ticket prices -- for now. Will success on the field follow?
"It's always going to be fun here with big crowds," Happ said. "It's a destination. But it's a different feeling in August and September when you're in the hunt and playing for divisions and getting to playoffs.
"There are pieces here that can be part of a division-winning team. We just have to keep moving in the right direction."
For now, that direction has taken the Cubs west to Iowa, where players, team executives and ownership will take center stage for one of baseball's crown jewel events. The only thing missing is a winning team.
"We're looking forward to the Field of Dreams game," Ricketts said. "Cubs fans are the best in the world and this is a well-deserved experience for them -- especially for our loyal Iowa fans. The Chicago Cubs are one of the original franchises in Major League Baseball's rich history. Suffice it to say, we plan on making championship history again."