The question again hanging over the Cubs at the trade deadline: If not now, when?

New York Times

10 hours ago

CHICAGO — In closing a controversial deal that aimed to end the Chicago Cubs' 108-year World Series drought, Theo Epstein memorably declared: 'If not now, when?'
Back in the summer of 2016, the Cubs had built a star-studded lineup and a dominant rotation that kept them on pace to win 100-plus games. Feeling the weight of the franchise's disappointing history, and sensing an enormous opportunity at the trade deadline, Epstein gave up future All-Star Gleyber Torres to get Aroldis Chapman, who had begun that season with the New York Yankees serving a suspension under Major League Baseball's Joint Domestic Violence, Sexual Assault and Child Abuse policy.
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Without Chapman that October and November, the Cubs believe they would not have advanced through three postseason rounds and won Game 7.
That history is relevant because Chapman is still an exceptionally talented closer, now with the Boston Red Sox, one of several underperforming teams that could swing the July 31 trade deadline by deciding to sell. And it's instructive when the Cubs are in a buying mood, feeling like they are having one of those magical years.
Though 1908 no longer hangs over their players and management team, the Cubs will be operating with a sense of urgency and from a position of strength. As a first-place team on the Fourth of July, the Cubs are in the market for a late-game reliever, a solid starting pitcher and a right-handed hitter. The larger context also matters.
The big-game energy has returned to Wrigleyville, enhancing ownership's portfolio of investments around the neighborhood. Cubs president of baseball operations Jed Hoyer entered this season in the final year of his contract, putting pressure on the entire front office. At the age of 23, Pete Crow-Armstrong is blossoming into a superstar. In a few months, All-Star outfielder Kyle Tucker will likely explore his options as a free agent.
Seven strong from Cade 😤 pic.twitter.com/B9XxviMioX
— Chicago Cubs (@Cubs) July 4, 2025
The Cubs are 52-35 after sweeping the Cleveland Guardians out of Wrigley Field with Thursday night's 1-0 victory, which featured seven stout innings from rookie pitcher Cade Horton, yet another bullpen group effort and Matt Shaw's sacrifice fly off Emmanuel Clase in the 10th inning. A crowd of 38,450 watched the Cubs increase their lead to four games in the National League Central.
Again, the question will be asked: If not now, when?
'Let's wait (to) make that determination,' said Hoyer, who previously worked as Epstein's longtime general manager in Chicago. Experience has taught Hoyer that so much will happen in the final month before the trade deadline, and he noted that the Chapman transaction wasn't finalized until July 25 that year.
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'When you think about that deal, it wasn't about playoff odds,' Hoyer said. 'That was about World Series probabilities. You add a dominant closer like that because there was a gap for us. We talked over and over throughout August and September about not using him for more than three-out saves because we wanted to be able to unleash his talent in the postseason to get to the World Series.'
The Cubs were fortunate in that the Yankees, a perennial contender, sold at the trade deadline for the first time in a generation. That will be part of the scoreboard-watching this July, seeing what the Arizona Diamondbacks decide to do at the last minute, whether third baseman Eugenio Suárez and pitchers Merrill Kelly and Zac Gallen become available.
The Kansas City Royals are among the clubs also in a holding pattern, with Seth Lugo profiling as the type of pitcher who would be a good fit in Chicago. MLB's gambling-related investigation into Cleveland pitcher Luis Ortiz, who was scratched from Thursday's start at Wrigley Field, could ultimately force the Guardians to unload major-league talent and reposition for the future.
Either way, the playoff format still accentuates the value of high-leverage relievers, which means the Cubs can fully believe in Daniel Palencia right now and still look to acquire another closer this summer. Héctor Rondón had been an excellent closer in 2015 (1.67 ERA, 30 saves) and the first half of 2016 (1.72 ERA, 14 saves), but Chapman pitched at a higher level, with an air of intimidation.
Then and now, adding Chapman would potentially keep him away from a team the Cubs would have to beat in October. While a 100 mph fastball is almost normal now, Chapman's velocity was a real outlier in 2016, when the Cubs had five healthy starting pitchers who routinely pitched deep into games. The current formula is more complicated.
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'There's a difference between playoff odds and World Series odds,' Hoyer said. 'Just getting in is not necessarily the ticket. High-leverage relievers do have a significant impact on your World Series odds. We obviously have those discussions all the time, but I don't think we're there yet in those discussions. We'll give that some time. There are different ways to think about what you're trying to accomplish.'
That is the internal mandate: Get creative. Perhaps that means a three-team deal, taking on contracts that go beyond 2025, targeting younger players or some combination of moves. Trade talks will likely accelerate after the All-Star break, given the timing of the MLB Draft (July 13-14) that occupies all 30 front offices.
The Cubs entered Thursday with a 97.1 percent chance to qualify for the playoffs, according to Baseball Reference, and a 16.1 percent chance to win the World Series. FanGraphs presented a slightly less optimistic, though still rosy, picture, setting Chicago's playoff odds at 90.3 percent, with a 5.7 percent probability of winning the World Series.
'Not to be Belichick about it,' said Hoyer, who graduated from Wesleyan University in Connecticut, the same school that once produced the famously grumpy football coach. 'But you have to take it one series at a time.'
(Photo by Geoff Stellfox / Getty Images)