5 Trades the Chicago Cubs should make at the deadline if they continue to struggle

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This is not going to be an article that has the Chicago Cubs receiving top prospects in return for aging veterans on rental contracts (mostly). We won’t see any trades within the division regardless of how badly the Cardinals need pitching, because it is exceedingly rare. The idea here was to focus on a couple of things:

  1. Who are players the Cubs don’t view as part of their long-term plans? 
  2. Who are teams that could use the players the Cubs would be looking to deal at the deadline?
  3. Who are players the Cubs might covet as pieces that can help them during their contention window, which they expected to open this year, on the teams that could match up as trade partners?

With that being said, here are five trades that the Cubs should be ecstatic to be offered at the trade deadline if they continue to play like one of the worst teams in baseball.

Trade 1: The Chicago Cubs trade LHP Drew Smyly to the Toronto Blue Jays for RHP Hagen Danner, LHP Jimmy Burnette, and INF Riley Tirotta

The 33-year-old Smyly is under contract through 2024 and has a mutual option for 2025 making him a valuable piece to a team in contention. He’s enjoying his best season in about a decade and if not for Yan Gomes spear-tackling him in the 8th inning against the Dodgers, he may have thrown the 24th Perfect Game in major league history earlier this year. 

That being said, while he could be a valuable piece for the Cubs moving forward as well, he is likely more valuable to them in terms of what they can get in return. The Cubs have Jameson Taillon and Justin Steele under team control through 2026 and 2027 respectively, along with Kyle Hendricks through 2024 and players like Hayden Wesneski, Ben Brown, and Jordan Wicks that could join the rotation as early as later this season. They also hope to be bidders in the Julio Urías/Shohei Ohtani sweepstakes this winter and therefore a player like Drew Smyly becomes a little superfluous.

Insert Hagen Danner and Jimmy Burnette. Both are 24 in AA right now, both have over 15 K/9, and both have incredible mustaches. Danner is a RHP that ranks as the 22nd best prospect in the Blue Jays system while Burnette is not currently ranked in the top 30 according to MLB Pipeline. The Cubs biggest problem with the bullpen this season has been an inability to miss bats, and these two solve that problem.

The last piece doesn’t bring a ton to the table as a 24 year-old in High A but he’s currently carrying a slash line of .317/.424/.573 with three homers and five stolen bases. He’s never played a level of minor league baseball where he was younger than the average player for that level and yet has also never had an OPS over .775, so there’s not a ton going on here, but a player with defensive positional flexibility in the infield has benefits.