
The St. Louis Cardinals are clearly in the midst of a rebuild, and the next logical move in this process could involve trading Pitcher.
With Helsley on an expiring contract and Spotrac estimating he could secure about $81 million in free agency next winter, it’s unlikely the Cardinals will re-sign him next offseason. Therefore, trading him now makes a lot of sense, particularly if St. Louis can secure a significant return.
Conor Liguori of Athlon Sports recently predicted the Cardinals would eventually trade Helsley to the Chicago Cubs in a rare interdivisional trade.

“In a trade with the Cardinals for Helsley, the Cubs would likely have to depart with two of their top 30 prospects but might be able to avoid dealing multiple players in the top 10,” Liguori wrote. “The Cubs could also add a controllable bullpen arm, like Tyson Miller, in the trade.
“If the Cardinals are out of the playoff race by the trade deadline, trading Helsley for prospects and improving the farm system may be the organization’s preferred course of action as they enter what they hope will be a quick rebuild. For the Cubs, Helsley can become the club’s full-time closer, and Pressly can transition to a setup man, a role he thrived in for several years with the Astros and Minnesota Twins.”
It will probably take more than just two top 30 prospects for the Cubs to acquire Helsley from the Cardinals. Given that Helsley is likely to be targeted by every playoff-contending team, St. Louis would probably prefer to trade him outside of the division. As a result, the Cubs may need to make a significantly over-the-top offer to secure him.
Ultimately, the Cardinals will be looking to maximize the value they get from their star closer. If the Cubs are willing to offer a strong deal, they could be the team to land Helsley.
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