Pirates' roster crunch may have just opened door for Cubs to land bullpen savior

The Chicago Cubs have tried to patch up their injured and underperforming bullpen with a series of reclamation projects, from old friends Drew Pomeranz and Aaron Civale to a one-game marriage with Jake Woodford. Nothing has really panned out quite yet, but the strategy remains a sensible one until the trade deadline imposes an ultimatum on acquiring serious upgrades for the roster.

Well, the Pittsburgh Pirates may have just created the perfect chance for the Cubs to get a reliever with high-leverage upside before that Aug. 3 deadline rolls around. Dennis Santana has been designated for assignment, bringing another player with closing experience to the market.

He's having a difficult year (hence the DFA decision), but he emerged as the Pirates' closer down the stretch in 2025 and put together a few solid seasons before this one. As long as the Cubs are giving anyone with a pulse a chance to prove their worth in the bullpen, wouldn't it make sense to bring Santana in for a brief audition?

Dennis Santana is perfect buy-low relief target for Cubs ahead of trade deadline

Santana, 30, is a free agent at the end of the season, so there's no real harm in claiming him off waivers (or signing him as a free agent if he makes it through the process). He's only making $3.5 million in salary this year, more than $2 million of which has already been paid out by the Pirates.

He's responsible for a 6.05 ERA and 5.48 FIP this year, giving in to the same command issues that plagued him earlier in his career. Save for a preternatural ability to get tons of swings on pitches outside the zone, he hasn't done a lot well in 2026.

However, that's a huge departure from where he was even a year ago, when he racked up 16 saves and a 2.18 ERA while emerging as a go-to leverage option following the trade of David Bednar. He was one of few pitchers in the league to produce a positive run value with his fastballs, off-speed pitches, and breaking balls, running one of the deeper arsenals you'll ever see a true reliever work with.

He obviously wouldn't walk into the closer role in Chicago given how poorly he's performed recently, but it's also not like there's a lot stopping him from quickly entering Craig Counsell's circle of trust. Daniel Palencia has been out of action more often than not this year, and he hasn't been quite as electric in the ninth inning as his World Baseball Classic performance suggested he would be.

Bringing in other, more proven relief options is still a must, but if the Cubs are in the business of giving opportunities to those with a strong track record, giving Santana a shot is a no-brainer decision.

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