Cubs Get Flexibility With Willi Castro, a Lefty Bullpen Arm With Taylor Rogers

The Cubs approached the trade deadline with pitching as their top priority. They traded for Michael Soroka on Wednesday to shore up the starting rotation and added Andrew Kittredge to the bullpen later that night. That didn’t stop them from making a trade to improve their hitters: Getting in on the Twins’ Thursday fire sale, Chicago acquired utilityman Willi Castro for two pitching prospects, Ryan Gallagher and Sam Armstrong. And right before the buzzer, the Cubs also acquired left-handed reliever Taylor Rogers from the Pirates for outfield prospect Ivan Brethowr. This was the second swap Rogers was part of within a roughly 27-hour span, after he went from the Reds to the Pirates in Wednesday afternoon’s Ke’Bryan Hayes deal.

The Cubs have one of the best lineups in baseball. They lead the majors in runs scored and the National League in wRC+. So they didn’t necessarily need to upgrade their offense before the deadline. Castro’s calling card is his versatility, and that’s the primary reason they acquired him. Just this year, he’s played every position but catcher and first base. Defensively, he’s probably a little in over his head at either of the premium up-the-middle positions — his career FRV at shortstop is -3 and -2 in center field — but he’s perfectly acceptable as a second baseman (2 FRV) or in either outfield corner (5 in left, -2 in right). In previous years, he was also slightly above average at third (2 FRV) before taking a step back this season (-3), though small-sample caveats certainly apply for his defensive metrics at any specific position because of how much he’s moved around. Only once has he logged more than 500 innings at an individual position in a season, and that was back in 2021 when he played 713 2/3 innings at second base with the Tigers.

That said, he is way more than just a multi-positional backup. At the plate, Castro has been solidly above average since joining the Twins in 2023; during those first seasons in Minnesota, he posted a combined 107 wRC+ and accumulated 5.4 WAR. This season, his offensive production has been slightly better — .245/.335/.407, 109 wRC+ — than in recent years because he’s tapping into his power more. He’s already smacked 10 home runs in 344 plate appearances after hitting a career-high 12 last year across nearly 300 more trips to the plate. That he is a switch-hitter only adds to his flexibility. He has been platoon neutral for his career, but he’s hitting left-handed hurlers much better this year (131 wRC+) than he has righties (100). Castro has been worth 1.1 WAR this season, a step back from his last two years despite his offensive improvements because his defensive value has declined. Some of this is due to a dip in his defensive metrics — his only plus position this season by FRV is left field — but it also has to do with the positional adjustment, as he’s spent more innings this season at positions further down the defensive spectrum; after playing 465 2/3 innings at shortstop in 2024 and another 211 1/3 in center field, he’s logged just 26 at shortstop this year to go along with a one-inning cameo in center.

Castro will reach free agency for the first time in his career at the end of this season, meaning he was always likely to be moved as soon when the Twins decided to sell. His name had been connected to a number of teams over the last few weeks, with the Mariners, Yankees, and Astros all showing interest as well. That the Cubs ultimately landed him comes as somewhat of a surprise. Jon Berti, the other utilityman on Chicago’s roster, has made just five starts since May 19, the day the Cubs recalled third baseman Matt Shaw from Triple-A. At the very least, the Cubs are getting a much better version of Berti to be a reliable depth piece. However, with the Twins, Castro was nearly an everyday player. Ideally, the Cubs won’t need to lean on him as much as Minnesota did, as they have established starters at every position. What Castro represents, then, is an opportunity for the Cubs to keep their starters fresh down the stretch. He could still end up playing frequently in a Ben Zobrist-type role, but barring injury, he almost certainly isn’t going to supplant any individual starting position player, with one possible exception: Shaw.

Shaw entered this season as the organization’s top prospect and ranked 22nd overall. He made the Opening Day roster but struggled to a 62 wRC+ in his first 18 games before he was optioned to Triple-A. He has produced a 90 wRC+ over 204 plate appearances since returning to the majors, and he’s caught fire in his 12 games since the All-Star break: Across 40 plate appearances, Shaw is slashing .359/.375/.744 with four homers and a 212 wRC+. He surely won’t sustain that level of production, but given his prospect pedigree, it’s possible he is closer to the player he’s been lately than what he showed during his first stint in the majors. Even so, Castro has been a better overall hitter this year than Shaw (109 wRC+ vs. 83), so if the rookie slips down the stretch, Castro would be a capable replacement.

Of course, offense has not been the issue for the Cubs. Pitching was their area of concern, and while they may not have done enough to reinforce their rotation, they did augment their bullpen, first with Kittredge and then Rogers. (You can read more about the Kittredge trade here.)

In his write-up of the Hayes deal that brought Rogers to the Pirates, Ben Clemens reasoned that Pittsburgh only acquired Rogers to offset the money owed to Hayes, and that Rogers probably would be flipped to another contender before the deadline. That’s exactly what transpired. Caleb Thielbar has pitched fairly well out of the Cubs bullpen as a lefty setup man, but the only other left-handed pitcher in their bullpen was Drew Pomeranz. Pomeranz made an impressive comeback at age 36 after multiple significant arm injuries the last few years. He had allowed just a single unearned run across 25 appearances through the end of June, but he has looked a little shaky in July, giving up eight runs in 10 appearances.

Relief pitching has been a source of stress for the Cubs for most of the year. Two of the relievers they were counting on in high-leverage situations, Ryan Pressly and Porter Hodge, struggled and ultimately lost their jobs; Hodge was optioned to Triple-A on Wednesday, and Pressly was designated for assignment on Thursday. Only when Daniel Palencia was inserted into the closer role did the pen stabilize a bit. Overall, the Cubs relief corps ranks 14th in park- and league-adjusted ERA, though just 24th in park- and league-adjusted FIP.

So what are the Cubs getting with Rogers? As Ben wrote in his analysis of the Hayes trade on Wednesday: “[Rogers] might not look like a world-beater, but there’s no way to slice his statistics where he isn’t at least serviceable.” As for those statistics, Rogers has a 2.45 ERA across 33 innings this season and a career 3.28 ERA. At a position of such volatility, Rogers has pretty much never been bad, even though you’re always a bit surprised when you look at his numbers. He is greatly overperforming his peripherals this season (3.96 xERA, 4.12 FIP, 4.48 xFIP), and he’s running the worst walk rate of his career (13.0%) and his lowest strikeout rate (23.3%) since 2017. But even if his true talent lies somewhere between his actual numbers and his expected ones, he should still be a dependable arm for the Cubs down the stretch and an upgrade from what they had.

For Castro and Rogers, the Cubs shipped out three prospects. Minnesota received two Double-A pitchers in Ryan Gallagher and Sam Armstrong. Gallagher was a sixth-round pick in last year’s draft and quickly ascended through Chicago’s farm system. A 3.72 ERA paired with an excellent 5.31 strikeout-to-walk ratio in High-A this year recently earned him a promotion to Double-A. Across those two levels, he’s posted a 28.2% strikeout rate thanks to a significant uptick in fastball velocity as a pro. Here are Eric Longenhagen’s notes:

Gallagher is a vert-slot righty with a 90-92 mph fastball that punches above its weight a tad and is routinely located at the top of the zone, where it plays best. His most outstanding pitch is a screwball-style changeup in the 75-79 mph range, roughly 14 mph separation from his fastball. He scatters it all over the zone and below, and it moves enough to play against hitters of both handedness even when it finds the meat of the zone. His slider command is much more typical, and Gallagher’s slot helps create some artificial depth on that pitch, which also plays against hitters from both sides. He isn’t throwing many strikes with his secondary pitches, but both are playing like comfortably plus offerings. He’ll be a 40 FV on the Twins list as I update it.

Armstrong seems more like an organizational depth piece — he wasn’t ranked on any public Cubs prospect lists. A 13th-round pick out of Old Dominion in the 2023 draft, he has pitched to a 4.62 ERA and 19.3% strikeout rate this year in his second taste of Double-A. Per Longenhagen: “He’s sitting 93, throwing an above-average rate of strikes, stuff looks average or a shade below across the board.”

For Rogers, the Pirates received outfielder Ivan Brethowr. A college teammate of Gallagher’s at UC-Santa Barbara, Brethowr was a power-hitting right fielder in college, blasting 28 home runs in 112 games. Drafted in the seventh round last year, that power he demonstrated in college has disappeared as a pro. He debuted in Single-A last year and hit .169/.274/.253 in 23 games. He was promoted to High-A this year and has looked a little better — slashing .221/.398/.312 in 83 games — though he’s still not hitting for power. More worryingly, his contact rate is just 66%, which won’t be viable even if he does regain the pop he showed at UCSB.