Everything was set up for a night of redemption. The fans buzzed with cautious optimism, the kind you feel when your team is clinging to a playoff pulse. There had already been some dramatics and a ninth-inning grind that highlighted something larger—could be a bounce-back win and could be a defining late-May moment.

However, then came the unexpected. In some time, cheers became stunned silence at Wrigley. The Chicago Cubs, who had clawed to keep aspects close, stood helplessly as the game slipped out of their control. In addition, one moment, one inning, transformed the tone completely.

The team was on the verge of what could have been a stunning comeback win. Entering the 11th inning, the day was tied at 5-5. In addition, it looked like the Cubs could pull it off. But then came Ryan Pressly. He has been solid in his current appearances. However, the star took the mound in that game in a vital extra-inning moment. What came after was nothing short of a nightmare. Pressly faced seven batters without recording a single out, enabling nine runs to score. It was the most ever in a single extra-inning frame in the team’s history. This established an unfortunate team record and broke the old one set in 1921. He became only the eighth reliever in MLB history to face at least eight batters without retiring any.

It was a total disaster. Yet, the Cubs did not turn on Pressly. Instead, Collin Rea provided some much-needed thought process. “He is obviously a really good pitcher,” he said. “We all believe in him. It was just one of those nights where it was not going the way you wanted to, but come out tomorrow and get a series win”, he added. Rea’s words were more than just a reassurance for Pressly—they were a statement of belief in the team. The team had rallied earlier in the game, tying a two-run tie in the ninth inning. In addition, this was still the Cubs that fought after the collapse.

While Pressly’s meltdown was jarring, it was not entirely reflective of the star’s season thus far. Before that night, Pressly had allowed just one unearned run in his last 10 appearances. In addition, he spanned over 10 innings. Pressly’s fastball velocity remained steady at 93.3 mph, which matched last season’s data. However, his fight to miss bats was clear, with an 8.1 percent strikeout rate and 12.9 percent walk rate. The team’s manager, Craig Counsell, acknowledged that while Pressly had not fought in his past appearances, the star could not end hitters on this night. It was a rare failure in what had otherwise been a promising stretch for Pressly.

“I thought I executed my pitches really well,” Pressly said. “I was not really leaving anything over the middle part of the plate. I just did not get my job done. It sucks, but got to get ready to go tomorrow,” he added. Pressly is 36, and he had his right knee drained on April 22, which briefly limited his availability. The two-time All-Star reliever did not utilize that inactivity as an excuse. “Everything is fine”, he said. “Body felt great. Like I said, did not do my job tonight. Everybody else did,” he added.

From meltdown to momentum, can the Cubs afford to secure their $600M future?

The team’s resilience in the face of Pressly’s historically brutal outing said more than the scoreboard. It highlighted the base with the power of the Cubs trying to establish something larger—a culture that does not implode after one bad night. That is exactly why the team now faces a team-defining choice: do they need to invest long-term in a future powered by Kyle Tucker and Pete Crow-Armstrong?

Financially, it is a stretch. The Cubs have not provided a contract north of $200 million in team history. However, with the Jays currently shelling out $500 million to retain Vladimir Guerrero Jr., the market is transforming. Jon Heyman thinks the Cubs will not match a more than $500M tag for PCA, saying, “That is not the Cubs. But you have got to make him a good offer and give it a shot.” The same thought process applies to Tucker, who is open to staying. The concern is whether the Cubs will finally break their spending pattern.

Still, data do not lie. Tucker carries a 168 wRC, walks more than he strikes out, and meshes effectively with Crow-Armstrong. Cooperatively, they have already launched 18 of the Cubs’ 22 home runs this season. PCA’s defense remains elite. In addition, his bat is heating up. If the team is serious about ignoring nights like Pressly’s from defining their season, locking in this duo could be the first—and most effective—step forward.

The Cubs can not afford to stay passive. One bullpen collapse will not define the team’s season; however, failing to extend Tucker and PCA just could. If the Cubs think of transforming from surviving games to establishing a dynasty, the time to commit is now. Bet on the future—and risk watching it walk away.

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