In 1997 the Chicago White Sox made the so-called “White Flag Trade”. Pitchers Wilson Alvarez, Danny Darwin and Roberto Hernandez were distributed to the San Francisco Giants at close of trading for a range of prospects, effectively ending any chance the White Sox had in the postseason.
The deal was the kind of move teams outside of the competition make through July 31st each year. But this one was particularly controversial because the White Sox were not clearly out of the running. On the last day of July – when the three pitchers were traded – the team was only three games behind the Cleveland Indians in first place, however the White Sox were in third place and only .500 at 53-53.
Owner Jerry Reinsdorf waved the white flag of the season. The White Sox had no winning mood, they didn’t attract fans and their chances of a special season were extremely slim.
“I’ve always thought about it, but unfortunately I had a boss,” said then White Sox GM Ron Schueler in a recent telephone interview. “Jerry has a unique saying over the years I’ve been with him. He doesn’t spend money he doesn’t have. For the most part, I have to agree with him.”
Reinsdorf summed it up more succinctly and told the Chicago Sun-Times: “Anyone who thinks we can catch Cleveland is crazy.”
Fast forward to 2021.
We’re five months from close of trading, but the team across Chicago could easily face the same dilemma. Indeed, it will come as a surprise if the Cubs aren’t in a similar position.
On paper, they’re too good in a mediocre league to be that far from the race, but they’re probably not good enough to be World Series competitors either.
Whoever wins headquarters is likely to be a strong underdog coming from the National League. At least that’s the mood in the final weeks of spring training.
And something else about the 2021 Cubs could make the decision even more difficult: half of the expected opening roster will be free agents in November. From Javier Baez to Zach Davies. From Kris Bryant to Craig Kimbrel. The list of players at the end of their contracts or team control is long.
“That brings with it some challenges dealing with guys and their worries about their futures,” said the new president of baseball operations, Jed Hoyer, at the start of the spring training session. “What’s unique about the Cubs is that we’ve had so many people over the last few years.”
How they got here
Winning a World Series has its cost. The cost of the Cubs was the following years after their championship in 2016. They were filled with poor performances. First it came under Joe Maddon and then again in David Ross’ first mini season at the helm in 2020.
Underachieving doesn’t mean the Cubs were a bad team. There have been successes. Their talent, character, and camaraderie led them to playoff appearances – but those successes also keep the notion that this group could have had more. Even they admitted it.
“If you go back 12, 13 months, it’s just marked by underperformance and uninspired play,” Epstein said during a bad stretch in 2019, about 14 months before leaving the team.
It’s an idea that Epstein repeated several times the further away the 2016 calendar was. And every time the Cubs brought back their core players only to let them down in the end.
Why did they collapse at the key times from 2018 to 2020? After all, these were the same players who won this World Series. They held it together in 2017 and tried to do it again but stayed behind in the NLCS. Then it got worse. A quick exit in October 2018 was followed by a non-playoff season in 19, followed by a two-game sweep by the Marlins last year. The Cubs have not won a playoff game since 2017.
The best explanation recently came from shortstop Javier Baez.
“I somehow got away from baseball mentally,” said Báez just last Friday. “Our hunger has slowed down.”
Baez has spoken about himself and his teammates in a similar way over the past few years. The Cubs felt, “We got it” in the years after the World Series, but feeling it or saying it didn’t make them do it.
Cubs brass is no exception. After breaking the longest championship drought in North American professional sport history, the news may have had to be improved. Instead, they fell into the trap of believing that because they did it once they would do it again. Those responsible slowly recognized this group was not will reach greatness again.
When the Cubs meekly fell on the Miami Marlins, it was the last straw. The team needed change. Epstein stepped out of the way to give Hoyer space to make his own long-term decisions – and to be accountable for the results. Epstein’s early departure was the first sign that the Cubs were beginning a transition. Does anyone really think they would have left if the team was close to another long run in October? Of course not.
One problem Hoyer needs to reverse is the club’s recent history, where he didn’t draw well on the hill. Not a single pitcher who was included in any of Epstein’s drafts from 2012 to 2020 is nearly 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 in for veterans to help a team in win-now mode, but that’s about it. As a result, the Cubs have had to spend a lot of money pitching over the years.
The rising cost of their pitching staff only added to the problem that there is a core of players all showing up at the same time: their free agent clocks are all ticking at once – and only Kyle Hendricks opted for one announced long-term deal (so far). Even veteran first baseman Anthony Rizzo’s contract, signed in 2013, will run – you guessed it – at the end of 2021.
“We’ve been saying all along that we want to keep some of these players,” said Hoyer. “That would be great, but it would be unrealistic to keep all the players who were part of 2016. That’s just the reality.”
Baez and Rizzo are the two stars who are most likely to return for the next season and beyond. Locking her up this spring would at least give Hoyer a basis for his long-term plan. The 2016 mainstay dismantling began when the team said goodbye to Kyle Schwarber, Jon Lester, and Albert Almora Jr. this winter.
His next chance to overhaul his team will come in 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 – unless he wasn’t waving. His Red Sox were the defending champions, hitting a 59-47 record on July 27, 2019 after beating the Yankees just three times in a row.
“We were walking into a two-week period, after the All-Star hiatus and before trading close, and I sit there and say, ‘What are we doing?'” Dombrowski recalled recently. “How do you jump off at this point?”
The Red Sox were in second place, but even after those three wins, they were eight games behind the Yankees. 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 after that it was like ‘son of a gun’,” he said.
It was actually eight in a row, and Boston missed the chance to retool. It’s what the aforementioned Yankees did so well in 2016 when they traded with Aroldis Chapman, Andrew Miller, and Carlos Beltran in the mid-season. The players they got back have helped build the foundation of the competing teams over the past few years. Dombrowski, who is now in charge of the Philadelphia Phillies, may have learned something in 19.
“If we’re close, but in my heart I know we can’t, I would make that decision to sell,” he said. “Fortunately, I haven’t been there too often.”
Neither did Hoyer. But it is coming. And he has to do what Brian Cashman did with the Yankees: do a home run with a business or two. As it is, it would take a Herculean effort on his manager’s part to get all of these potential free agents to think about gains and losses in terms of money and safety.
“I’m definitely not an expert on the big job,” joked Ross about running a team with so many free agents. “It’s on my radar, but I really appreciate the quality of the person we have in this locker room.”
Hoyer might have made it even more difficult for himself when the team added high-profile outfielder Joc Pederson and seasoned starter Jake Arrieta to the roster late in the off-season. In the winter prior to that point, the organization flirted with rebuilding, especially after Yu Darvish was sold to San Diego for four prospects (and Davies).
But the Cubs were able to reach a higher salary range later in the winter due to a number of factors, including the increased likelihood of fans starting the season at games and corporate sponsorship. Now, Hoyer’s team might just be good enough to keep him up at night in July.
Hoyer added: “We have to play well and be in a good position. To say otherwise would be imprecise but I am confident that we will play well.”
“I hope we’re on the buy side but those are the tough choices you have to make in this job when we’re not playing well.”
An AL manager asked to analyze the Cubs’ situation did not admire Hoyer’s position: “Threading this needle is really difficult. He has to get emotion out of it and talk to everyone in his organization when the decision isn’t obvious. Hearing the truth at this moment is important. ‘Can we argue?’ “
Hoyer can put all of this on the table for the moment. But he cannot avoid what is coming. If he doesn’t pull the trigger on some of the mid-season deals, he could reset the future of the Cubs even if the leaderboard says his team can play in October. July 31st, 2021 is what this Cubs season is all about.
“That’s my job,” said Hoyer. “I have to make that call. We have had a lot of people over the last few years and I hope they play great and we lead the division or right there in the race and we want to add something in July. That’s the best.” Case scenario.
“There is also a middle ground that makes it difficult.”