In 1997, the Chicago White Sox famously made what is known as the “White Flag Trade.” Pitchers Wilson Alvarez, Danny Darwin and Roberto Hernandez were dealt to the San Francisco Giants at the trade deadline for a slew of prospects, effectively ending any chance the White Sox had at the postseason.

The deal was the kind of move that teams out of contention make every year leading up to July 31. But this one was particularly controversial because the White Sox weren’t clearly out of the race. On the final day of July — when the three pitchers were traded — the team was just three games behind the first-place Cleveland Indians, however, the White Sox were in third place and just .500 at 53-53.

Owner Jerry Reinsdorf waved the white flag on the season. The White Sox had no winning vibe, they weren’t drawing fans and their chances at having a special season were extremely slim.

“I was always thinking about going for it, but unfortunately I had a boss,” then-White Sox GM Ron Schueler said in a recent phone interview. “Jerry has a unique saying over the years I was with him. He doesn’t like to spend money that he doesn’t have. For the most part, I have to agree with him.”

Reinsdorf summed it up more succinctly at the time, telling the Chicago Sun-Times, “Anyone who thinks we can catch Cleveland is crazy.”

Fast forward to 2021.

We’re five months from the trade deadline, but the team on the other side of Chicago could easily be facing the same dilemma. In fact, it’ll be a surprise if the Cubs aren’t in some kind of similar position.

On paper, they’re too good, in a mediocre division, to be that far out of the race, but they’re also not likely to be good enough to be World Series contenders.

Whoever does win the Central is likely to be heavy underdogs to come out of the National League, at least that’s the vibe heading into the final weeks of spring training.

And there’s one more thing about the 2021 Cubs that could make the decision even harder: Half of the likely Opening Day roster will be free agents come November. From Javier Baez to Zach Davies. From Kris Bryant to Craig Kimbrel. The list of players at the end of their contracts, or of team control, is long.

“That presents some challenges, dealing with guys and their anxieties about their future,” new president of baseball operations Jed Hoyer said at the start of spring training. “The one that’s unique to the Cubs is that we have so many guys in walk years.”

How they got here

Winning a World Series has its costs. The cost for the Cubs was the ensuing years after their championship in 2016. They were filled with underachievement. First, it came under Joe Maddon, and then, once more, in David Ross’ first mini-season at the helm in 2020.

Underachieving doesn’t mean the Cubs were a bad team. There were successes. Their talent, character and camaraderie led them to playoff appearances — but those accomplishments also don’t wash away the idea that this group could have had more. Even they have admitted as much.

“If you go back 12, 13 months, it’s just been marked by underachievement and uninspired play,” Epstein said during one bad stretch in 2019, about 14 months before leaving the team.

It’s a notion Epstein repeated several times the further the calendar got from 2016. And each time, the Cubs would bring back their core players only to have them disappoint in the end.

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Why did they crumble at the most important times from 2018 to 2020? After all, these were the same players who won that World Series. They held it together in 2017, attempting to repeat, but fell short in the NLCS. Then things got worse. A quick October exit in 2018 was followed by a non-playoff season in ’19, which was followed by a two-game sweep by the Marlins last year. The Cubs haven’t won a playoff game since 2017.

The best explanation came recently from shortstop Javier Baez.

“I kind of got away from baseball, mentally,” Báez said just last Friday. “Our hunger kind of slowed down.”

Baez has spoken about himself and his teammates in a similar manner over the past few seasons. The Cubs had an air of “we got this” about them in the years after the World Series, but feeling it or saying it didn’t translate to doing it.

Cubs brass isn’t exempt. After breaking the longest championship drought in the history of North American professional sports, perhaps the message needed a tuneup. Instead, they fell into the trap of believing that because they did it once, they would do it again. Slowly, the people in charge realized this group wasn’t going to achieve greatness again.

When the Cubs fell meekly to the Miami Marlins, it was the final straw. The team needed change. Epstein got out of the way to allow Hoyer room to make his own long-term decisions — and to be accountable for the results. Epstein’s early departure was the first sign the Cubs were beginning a transition. Does anyone really think he would have left if the team was on the verge of another long October run? Of course not.

One issue Hoyer will need to turn around is the club’s recent history of not drafting well on the mound. Not one pitcher taken in any of Epstein’s drafts from 2012 to 2020 has come close to being a regular starter on the team, and only a small handful have seen time in the bullpen. Draft picks Dylan Cease and Zack Godley were traded for veterans to help a team in win-now mode, but that’s really it. As a result, the Cubs have been forced to spend a lot of money on pitching over the years.

The mounting cost of their pitching staff only added to the problem that comes with having a core of players who all came up around the same time: Their free-agent clocks are all ticking at once — and only Kyle Hendricks has signed up for a long-term deal (so far). Even veteran first baseman Anthony Rizzo’s contract, signed in 2013, is — you guessed it — up at the end of 2021.

“We’ve said all along, we’d like to keep some of these players,” Hoyer stated. “That would be great, but it would be unrealistic to keep all of the players that were part of 2016. That’s just the reality.”

Baez and Rizzo are the two stars most likely to return next season and beyond. Locking them up this spring would at least give Hoyer a foundation for his long-term plan. Some shedding of 2016 mainstays began when the team said goodbye to Kyle Schwarber, Jon Lester and Albert Almora Jr. this winter.

His next chance to rework his team will come midsummer … or will it?

The big decision

In 2019, then-general manager of the Boston Red Sox, Dave Dombrowski, had his own white flag moment — except he didn’t wave it. His Red Sox were the defending champions and on July 27, 2019, had a 59-47 record having just won three straight against the Yankees.

“We went into a two-week period, after the All-Star break and before the trade deadline, and I’m sitting there saying, ‘What do we do?'” Dombrowski recalled recently. “How do you jump off at that point?”

The Red Sox were in second place but eight games behind the Yankees even after those three wins. So they were the opposite of the 1997 White Sox. A team with a good record but far from first place. Dombrowski decided to stand pat.

“Then we lost seven in a row, and afterward it was like, ‘Son of a gun,'” he said.

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Actually, it was eight in a row, and Boston missed a chance to retool. It’s what the aforementioned Yankees did so well in 2016, when they traded Aroldis Chapman, Andrew Miller and Carlos Beltran midseason. The players they got back have helped form the foundation of contending teams in the years since. Dombrowski, now in charge with the Philadelphia Phillies, might have learned something in ’19.

“If we’re close, but in my heart I know we can’t do it, I would make that decision to sell,” he said. “Luckily, I haven’t been there too many times.”

Neither has Hoyer. But it’s coming. And he needs to do what Brian Cashman did with the Yankees: Hit a home run with a trade or two. As is, it would take a herculean effort by his manager to keep all those would-be free agents thinking about wins and losses over money and security.

“I’m definitely not an expert on getting the big contract,” Ross joked about leading a team with so many free agents. “It’s on my radar, but I really value the quality of the human being we have in that locker room.”

Hoyer might have made it even tougher for himself when the team added quality outfielder Joc Pederson and veteran starter Jake Arrieta to the roster late in the offseason. The winter, prior to that point, had the organization flirting with a rebuild, especially after Yu Darvish was traded to San Diego for four prospects (and Davies).

But the Cubs were able to reach a higher payroll budget range later in the winter due to several factors, including the increased likelihood of fans at games to start the season along with corporate sponsorships. Now, Hoyer’s team might be just good enough to keep him up at night come July.

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Hoyer added: “We need to play well and be in a good position. Saying differently would be inaccurate, but I have every confidence we’ll go out and play well.”

“My hope is we’re on the buy side of that, but those are the tough decisions you have to make in this job if we’re not playing well.”

One AL executive, asked to analyze the Cubs’ situation, didn’t admire Hoyer’s position: “Threading that needle is really hard. He has to take emotion out of it and talk with everyone in his organization if the decision isn’t obvious. Hearing the truth in that moment is important. ‘Can we contend?'”

Hoyer can table all this for the moment. But he can’t avoid what’s coming. If he doesn’t pull the trigger on some midseason deals, he could be setting the Cubs’ future back even if the standings say his team can play in October. July 31, 2021, is what this Cubs season is all about.

“That’s my job,” Hoyer said. “I’ll have to make that call. We have a bunch of guys on their last years, and I hope they play great and we’re leading the division or right there in the race and looking to add in July. That’s the best-case scenario.

“There’s also a middle ground that makes it hard.”