MLB Insider Proposes Blockbuster Trade Idea Solving Three Cubs' Issues
The Chicago Cubs had a stellar first half of the MLB season, finishing with a 57-39 record, good for first place in the National League Central and the second-best record in the NL. However, with the incredible first half, the Cubs sit just a game above the Milwaukee Brewers in the division.
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Like many teams, Chicago will be buyers at the 2025 MLB trade deadline. But with the Brewers' strong push before the All-Star break, the Cubs may have to be even more aggressive to put themselves in a position to win their division and make a run in the postseason.
The Cubs' primary need is starting pitching. But, after that, the Cubs could use a third baseman and some bullpen help. The two main starting pitching names thrown around are Pittsburgh Pirates' pitcher Mitch Keller and Miami Marlins' pitcher Sandy Alcantara, as the two teams are obvious sellers at the deadline.
Pirates' reliever David Bednar has also been a hot name for top relief pitching. There are expected to be many trades with top targets involved and under-the-radar guys for contending teams to go after.
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On Sunday, the New York Post's MLB Insider Jon Heyman proposed a blockbuster five-player trade that would land the Cubs three players at the three positions of need.
Heyman proposed the Pirates trade Keller, Bednar, and third baseman Ke'Bryan Hayes to the Cubs for third baseman Matt Shaw and top outfield prospect Owen Caissie in return.
At first glance, this trade proposal is loaded with talent. Keller might be the top starting pitching option on the market. Bednar is one of the top closer options available, and Hayes is still a young, developing player with elite defense at third base. However, to get a lot of talent, you must give some too.
Chicago Cubs manager Craig Counsell (11) is interviewed in the dugout before the game against the Houston Astros at Daikin Park. Troy Taormina-Imagn ImagesTroy Taormina-Imagn Images
Shaw was a former top prospect for the Cubs, but has struggled at the major league level. As for Caissie, the young prospect has had an impressive season in the minor leagues, batting .278 with a .961 OPS. He's hit 19 home runs and driven 42 guys in.
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But, recently, he has caught fire. Caissie hit .316 with a 1.040 OPS in June and has hit .394 with a .1578 OPS in July. The Cubs' top outfield prospect has seven home runs, nine RBI, and six walks in eight games in July.
"The Cubs are scouting the Pirates (as are most contenders). Keller will be one of the better starters available and Hayes is a great defender who needs a change of scenery," Heyman wrote (h/t The Sporting News). "The Pirates seek and need young guys who can hit."
The trade would deliver a one-stop shop for everything the Cubs need at the deadline, but it would come at the cost of some of their top prospects. However, if the Cubs plan on getting a top-level starter, they might have to plan on shopping a top prospect regardless.
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Another added advantage of this proposal for the Cubs is that none of the players involved are in the rental business. Keller signed a five-year, $77 million contract in 2024 and is under team control through 2028. Bednar has another year of arbitration in 2026, and Hayes is in the fourth year of an eight-year, $70 million contract with a club option in 2030.
Who knows if this trade would ever be agreed to, but it would solve all the Cubs' problems and the Pirates would get a couple of young, talented prospects to build their future on.
Related: Cubs Could Poach Yankees 31 Home Run Target, Per MLB Writer
This story was originally reported by Athlon Sports on Jul 15, 2025, where it first appeared.
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