{"id":758453,"date":"2026-07-22T12:21:21","date_gmt":"2026-07-22T12:21:21","guid":{"rendered":"https:\/\/www.rawchili.com\/mlb\/758453\/"},"modified":"2026-07-22T12:21:21","modified_gmt":"2026-07-22T12:21:21","slug":"column-how-aggressive-will-chicago-cubs-be-at-trade-deadline","status":"publish","type":"post","link":"https:\/\/www.rawchili.com\/mlb\/758453\/","title":{"rendered":"Column: How aggressive will Chicago Cubs be at trade deadline?"},"content":{"rendered":"

The Chicago Cubs<\/a> will be buyers at the trade deadline for the third time in the last four seasons, which means president Jed Hoyer will be active again.<\/p>\n

Just how active is anyone\u2019s guess, with the Cubs holding onto the top wild-card spot before Tuesday\u2019s 11-2 win over the Detroit Tigers, but six games behind the Milwaukee Brewers<\/a> in the National League Central.<\/p>\n

If the status quo plays out, they\u2019ll host a best-of-three wild-card series at Wrigley Field in October, just like last year, while the Los Angeles Dodgers and Milwaukee Brewers get byes again.<\/p>\n

\u201cI think you have to go into the deadline thinking about it analytically,\u201d Hoyer said last Friday. \u201cThinking about OK, getting a bye is effectively winning a series and weakening your opponent in the next series. That\u2019s a really big deal. So if the odds say that you can do that, then that\u2019s a different equation than if not. I think you have to be aware of those things.\u201d<\/p>\n

The Cubs have a 79% chance of making the playoffs, according to FanGraphs, but only an 8.6% chance of winning the division and a 4.8% chance of a first-round bye.<\/p>\n

\"ChicagoChicago Cubs third baseman Alex Bregman throws to first base on a ground ball in the first inning of a game against the Minnesota Twins at Wrigley Field in Chicago on July 18, 2026. (Chris Sweda\/Chicago Tribune)<\/p>\n

In a fantasy world that only exists on the internet and selected Cubs blogs, the team will be in on Tarik Skubal, Mason Miller, Joe Ryan, Josh Hader or maybe another elite pitcher who may be available for a slew of top prospects.<\/p>\n

In the real world we\u2019ve been living in over the last four years of the Hoyer regime, the Cubs are more likely to be in on Freddy Peralta, Jos\u00e9 Soriano, Casey Mize, Brooks Raley or a few other pitchers who\u2019ve dealt with injuries or recent struggles and won\u2019t cost them an arm and a leg, prospect-wise.<\/p>\n

But who knows?<\/p>\n

Perhaps the 2016 reunion weekend<\/a> will spur Hoyer to make a big, bold move at the Aug. 3 deadline. Maybe Chairman Tom Ricketts will give Hoyer the leeway to go for it, as he did last January with the signing of Alex Bregman to a five-year, $175 million deal while the Bears were mounting an epic comeback against the Green Bay Packers in the playoffs.<\/p>\n

Either way, the spotlight will be on Hoyer, and to a lesser extent Carter Hawkins, the general manager who generally stays out of sight.<\/p>\n

Here\u2019s a brief reminder of what they\u2019re done the last three deadlines:<\/p>\n

In 2023, Hoyer was a likely seller until the team went on an eight-game win streak in late July, pulling to within 3 1\/2 games in the Central and getting in the thick of the NL wild-card chase. Instead of dealing Cody Bellinger and Marcus Stroman, Hoyer went the other route and acquired third baseman Jeimer Candelario and cash from the Washington Nationals for prospects Kevin Made and DJ Herz, along with reliever Jos\u00e9 Cuas from the Kansas City Royals for outfielder Nelson Vel\u00e1zquez.<\/p>\n

\"ChicagoChicago Cubs’ Christopher Morel celebrates after hitting a three-run walk-off home run in the ninth inning of a game against the Chicago White Sox at Wrigley Field on Wednesday, Aug. 16, 2023. (Chris Sweda\/Chicago Tribune)<\/p>\n

Neither Candelario nor Cuas made a big impact, but the Cubs were in position for a wild-card spot in mid-September until a 4-11 stretch did them in. The collapse cost manager David Ross his job, even as Ricketts told reporters on the final day of the season: \u201cRossy had a great season, and the players play hard for him. He\u2019s our guy.\u201d<\/p>\n

Well, that was technically true at the time. But soon Craig Counsell was his guy, agreeing to a five-year, $40 million deal to work his magic in Chicago.<\/p>\n

In 2024, the Cubs flopped in May after a strong start and had the fourth-worst record in the National League at the deadline, ending any potential drama. Hoyer dumped Christopher Morel on the Tampa Bay Rays in a deal that netted third baseman Isaac Paredes, who was later part of the offseason deal that brought in Houston Astros star Kyle Tucker, a one-and-done guy. The only other move was dealing Mark Leiter Jr. to the New York Yankees, but no one really cared.<\/p>\n

Last year was Hoyer\u2019s big opportunity to channel his inner Theo Epstein<\/a>, with the Cubs neck-and-neck with the Brewers in the Central and looking at a chance to clinch that coveted first-round bye. Ricketts handed Hoyer an extension three days before the deadline, showing faith in his guy, who had gone playoff-free in his first four seasons.<\/p>\n

Once again, getting pitching help was the primary goal,<\/a> but Hoyer wound up getting a soon-to-be-injured starter in Michael Soroka, two leverage relievers in Andrew Kittredge and Taylor Rogers, and a utilityman in Willi Castro. He managed to keep his top prospects \u2014 Mois\u00e9s Ballesteros and Owen Caissie \u2014 and rookie Matt Shaw.<\/p>\n

\u201cThe asking price we felt like was something that we couldn\u2019t do to the future,\u201d Hoyer said after the deadline passed. \u201cIn the end, the asking price on those guys would have been so detrimental to our future that we decided against it.\u201d<\/p>\n

Hawkins later defended the moves to ESPN<\/a>, telling reporter Jesse Rogers: \u201cTeams are trying to find that guy that can lock down the eighth or ninth inning, but that also costs a lot. That costs a lot of future wins. We have a responsibility to the 2025 Cubs but also the 2032 Cubs. That\u2019s not always popular in the moment, but it\u2019s decisions we have to make.\u201d<\/p>\n

That didn\u2019t go over well with Cubs fans, who weren\u2019t really thinking about 2032 at the time.<\/p>\n

Two weeks after the trade deadline, the Cubs were nine games behind the Brewers and spent the rest of the season focusing on the wild card. They wound up beating the San Diego Padres at Wrigley before losing the National League Division Series to Milwaukee in five games. The season was considered a stepping stone to better things in \u201926.<\/p>\n

None of the four deadline acquisitions returned, and Kittredge was even sent back to Baltimore, where the Cubs got him. Caissie was dealt after the season to the Miami Marlins to bolster the rotation with the addition of Edward Cabrera, who currently remains on the 15-day IL and is not close to returning. Ballesteros is trying to rediscover his stroke at Triple-A Iowa, and Shaw was made into a utilityman when the Cubs signed Bregman. He\u2019s also out for a while with a wrist injury.<\/p>\n

Now we\u2019re back to watching what Hoyer will do next. He has always been an advocate of \u201cintelligent spending,\u201d<\/a> which is \u2026 what exactly?<\/p>\n

\u201cObviously there\u2019s a danger in free agency of committing a lot of years and a lot of dollars to players in sort of a decline phase of their career,\u201d Hoyer said back in \u201921 when he started the reboot. \u201cYou always have to be mindful of what the biggest value is in that contract. Free agency is valuable. Free agency is also dangerous.\u201d<\/p>\n

So here we are, with two weeks to go until the deadline and 2032 still a long way away.<\/p>\n

It\u2019s Hoyer\u2019s most crucial trade deadline to date.<\/p>\n

Keep him in your thoughts.<\/p>\n","protected":false},"excerpt":{"rendered":"The Chicago Cubs will be buyers at the trade deadline for the third time in the last four…\n","protected":false},"author":2,"featured_media":758454,"comment_status":"","ping_status":"","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[2399],"tags":[5,12679,138,24,4245,161,93971,884,4,3449,93972],"class_list":["post-758453","post","type-post","status-publish","format-standard","has-post-thumbnail","category-chicago-cubs","tag-baseball","tag-carter-hawkins","tag-chicago","tag-chicago-cubs","tag-chicagocubs","tag-cubs","tag-cubs-buyers-or-sellers","tag-jed-hoyer","tag-mlb","tag-mlb-trade-deadline","tag-when-is-the-mlb-trade-deadline"],"share_on_mastodon":{"url":"https:\/\/channels.im\/@mlb\/116963605750560808","error":""},"_links":{"self":[{"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/posts\/758453","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/users\/2"}],"replies":[{"embeddable":true,"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/comments?post=758453"}],"version-history":[{"count":0,"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/posts\/758453\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/media\/758454"}],"wp:attachment":[{"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/media?parent=758453"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/categories?post=758453"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.rawchili.com\/mlb\/wp-json\/wp\/v2\/tags?post=758453"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}