Jake Woodford's 2026 season reads like a well-traveled guy checking bags at every gate in the league. Drafted 39th overall by the Cardinals back in 2015 and a big leaguer since 2020, Woodford has bounced between six different organizations since early 2025 alone, with MLB stints for the D-backs, Brewers and now the Cubs, plus minor league detours through the Yankees, Rockies and Rays systems. The guy is basically the sport's most well-traveled bullpen arm, and Chicago just made him a two-time Cub in the span of about two weeks.
MLB Trade Rumors confirmed the move Friday, and it's the kind of low-stakes transaction that would normally fly under the radar if the timing weren't so on-the-nose.
Cubs Re-Sign Jake Woodford To Minor League Deal t.co/KMH00lSjuj
Woodford's first go-round in Chicago didn't last long. He'd signed a major league contract with the Cubs on July 4, but got designated for assignment shortly after to clear a roster spot for reliever Phil Maton, who was coming off the injured list. His lone appearance in a Cubs uniform wasn't pretty either: 2 innings, 3 earned runs on 5 hits including a homer, 3 strikeouts and no walks. He went unclaimed on waivers, which usually means a guy's headed elsewhere for good. Instead, the Cubs just... signed him again.
That's not as strange as it sounds once you factor in what Chicago's pitching staff actually looks like right now. The rotation has been gutted by injuries, with Cade Horton, Justin Steele, Edward Cabrera, Ben Brown and Jameson Taillon all currently on the IL alongside multiple relievers. That's not a depth problem, that's a five-alarm fire, and it explains why a team would rather have a known-quantity swingman parked in Triple-A Iowa than gamble on an unknown. Woodford's best stretch of baseball actually came against these same NL Central circles, back in 2022 with St. Louis, when he posted a 2.23 ERA over 48 1/3 innings in 27 appearances. He's never been a star, but he's been a guy who can eat innings without wrecking a bullpen.
Nobody's going to confuse this with a trade-deadline blockbuster. But minor league fliers like this are exactly the kind of moves contenders lean on when the alternative is calling up a Double-A arm mid-Twins-series. Woodford stashed in Iowa gives the Cubs rotation depth and length insurance without burning a 40-man spot, and if the injury list gets any longer, don't be surprised if he's back in Chicago for a third stint before September.