Jed Hoyer changed the entire narrative that's surrounded him for pretty much all his time as the Chicago Cubs' president of baseball operations, aggressively adding ahead of this week's trade deadline, acquiring proven pieces like Kevin Gausman and Clay Holmes to shore up the pitching staff.
It was one of Hoyer's busiest trade deadlines and positions the Cubs to be a legitimate contender come October. Across the league, several former Cubs players (and a critical Cubs prospect) were traded, as well. Here's a rundown of those moves and how they could impact Chicago.
Several NL contenders made key trades involving former Cubs players
Caleb Kilian
Caleb Kilian, who first came to the Cubs organization in the 2021 Kris Bryant trade, made his MLB debut with the team the following year and made a handful of largely ineffective appearances before coming full-circle and re-joining the San Francisco Giants prior to the 2026 campaign.
The right-hander is in the midst of his best season to-date, accumulating a 3.59 FIP across 45 appearances. That performance drew the eye of the Philadelphia Phillies and Dave Dombrowski, who acquired Kilian in the deal that also brought Luis Arraez to Philly on Monday.
It adds a valuable relief piece to Don Mattingly's bullpen, which entered Tuesday ranked 23rd in ERA. The clock is ticking on this Phillies core and the hope is that Kilian and Arraez can help push them over the top in their quest to bring a championship back to the city before it's all said and done.
Gage Workman
Remember when there was a chunk of Cubs fans clamoring for Gage Workman to play a meaningful role for the team last year? Yes, the same Gage Workman who owns a career 45 OPS+. That was fun.
Anywho, since his brief stint on the North Side ended, Workman has suited up for both the Chicago White Sox and Detroit Tigers and the latter sent him to a new organization Monday afternoon, trading him to the San Diego Padres along with Casey Mize in exchange for minor league pitchers Jackson Wolf and Kash Mayfield.
I'd be shocked if Workman even appears in a game for the Friars. He's batting just .158/.158/.395 in 38 plate appearances this season. Mize was the key piece for San Diego in the deal - now we see if he can help carry the team into the postseason.
Brooks Raley
A former sixth-round pick of the Cubs way back in 2009, Brooks Raley is not only still hanging around, but was a hot commodity at the trade deadline - and it's not hard to see why. The southpaw made 45 appearances for the New York Mets, pitching to a 1.96 ERA and, dating back to the start of the 2022 season, has tossed nearly 200 innings of 2.42 ERA ball.
Now, he'll join Kilian in Philadelphia in the new-look Phillies bullpen after David Stearns traded him to the Phillies in exchange for a pair of prospects, Luke Gabrysh and John Spikerman. The 38-year-old is a free agent at season's end, and given where he's at in his career, he'll be as motivated as anyone to win a ring in Philly.
Codi Heuer
A key piece in the 2021 Craig Kimbrel trade with the White Sox, Codi Heuer showed a brief flash of brilliance for the Cubs, posting a 3.14 ERA following his move across town, but injuries hit him hard and he's been a near-non-factor at the big-league level ever since. This season, he's made eight appearances with the Guardians and that's the most action he's seen since that 2021 campaign.
Even so, he was traded not once, but twice this week. First, Cleveland traded him to the Brewers (and nightmares of Milwaukee miraculously unlocking him immediately flooded my mind), but then he was flipped again, landing in Baltimore by the time the dust settled in exchange for cash considerations.
Zyhir Hope
If you want to know how the Zyhir Hope trade will impact the Cubs, you got the answer on Tuesday night, when Tarik Skubal made his Los Angeles Dodgers debut at Wrigley Field.
Skubal provided an immediate (and massive) boost to the Dodgers' already sky-high World Series odds as they look to join the elite club of MLB three-peat champions. A free agent at season's end, the left-hander seems likely to set a new high-water mark for a pitcher on the open market (CBA changes could impact that).
The long story short? If the Cubs and all their trade deadline additions want to return to the Fall Classic this October, the road runs through Skubal and the Dodgers.
