Cubs history has plenty of heartbreak, and a ranking of 25 of its biggest disappointments still stings. Entries include decades of postseason futility after 1945, Craig Counsell's 83-79 2024 finish one game short, and the Rafael Palmeiro trade. 💔
Scott Boras is urging teams to sign free agents before the Dec. 2 lockout, and the Cubs, reportedly an expected bidder for Tarik Skubal, are positioned to act. Boras' recent deals with Hoyer (Bellinger, Bregman) suggest a workable relationship. 🔒
Nico Hoerner slid to .263 and an 84 OPS+ in 2026, yet his .297 xBA and elite contact marks hold steady. Craig Counsell says luck hits him hardest because he puts the ball in play so much. BABIP swings (.313 to .275) look like the culprit. 🎲
Jackson Cluff, a 29-year-old shortstop who joined the Cubs on a minor-league deal in mid-August after the Mets released him, has retired. He hit .148 in 18 games for Triple-A Iowa and never reached the majors in an eight-year pro career.
Teruaki Sato's Triple Crown season in Japan (39 HR, .991 OPS) makes him tempting, but the Cubs reportedly lack a clean fit. Bregman holds third and Busch first, so Sato would only fit in right if Suzuki leaves, and re-signing Suzuki looks like the safer play.
Cubs second-rounder Caden Sorrell looks like an early win from the 2026 class: .295/.347/.523, 131 wRC+, five homers and eight steals in 22 Single-A games. MLB Pipeline ranks him seventh in the system, behind three outfielders, which could make him interesting in trade talks. 🌽
Offseason chatter is already heating up: Mason Miller, Brandon Woodruff, Tarik Skubal and an NPB arm are all floated as possible Cubs targets. Nothing is confirmed, and the proposed Miller deal reportedly carries a steep farm-system cost. 🔍
The Cubs are reportedly listed among potential suitors for Tarik Skubal, with over $100M coming off the books. But a deal projected above $300M would top their $200M ceiling, and Jed Hoyer's history suggests long odds against the Dodgers and Mets. 🎯
Cubs could pursue Dodgers free agent Alex Vesia, a lefty with a 32.4% career strikeout rate, rather than lean on Ryan Rolison. Rolison's 3.14 ERA came with a 4.03 xERA, so regression looms. Bat-missing is the pitch. ⚾
A Cubs Roundtable writer floated Matt Shaw as a possible offseason trade chip for pitching help. Shaw hit .237 with five homers in 77 injury-hampered games in 2026, and the infield is crowded. Nothing is confirmed. 🔍
Dansby Swanson hit .213 with 19 homers, 69 RBIs and 17 steals in 126 games, and the Cubs still owe him $78 million over the next three seasons, per Spotrac. The bill arrives after a Wild Card sweep by the Padres. 💸
Speculation: with the rotation facing free-agent holes, Seibu Lions righty Kona Takahashi is floated as a low-cost Cubs target. He posted a 2.54 ERA in 138 1/3 innings in 2026 and is a groundball arm overshadowed by Taira and Sato. 🎯
Catching prospect Owen Ayers, the Cubs' No. 2 prospect, started 2026 at High-A and ended it with a Wrigley locker, soaking up big league clubhouse life. With Carson Kelly's $7.5M mutual option looming, he's a catching-future storyline. 🔒
Cubs could target impending free agent Mauricio Dubón, a Gold Glove-nominated utility man from the Braves. He wouldn't replace Happ or Suzuki's bats, but a .719 OPS and 99 wRC+ plus elite versatility could ease the outfield losses. 🧰
Ex-Cub Trevor Megill closed out the Brewers' 3-2 World Series Game 1 win, a bumpy ninth with a couple of singles. Chicago picked him in the 2019 Rule 5 Draft, then waived him in Nov. 2021 after an 8.37 ERA. NL Central discards, now on the big stage. 🎯
Speculation floats a Cubs trade for Guardians OF Steven Kwan, a four-time Gold Glover with one year left, if Seiya Suzuki and Ian Happ leave. A proposed package of Kevin Alcantara and B.J. Murray could work, but nothing is agreed. 🧤
Pete Crow-Armstrong is stacking hardware: Sporting News MLB Player of the Year, voted on by fellow players, plus The Fielding Bible's Defensive Player of the Year. Cubs award season opens with the center fielder in front. 🏆
Cubs' pitching plan: Tarik Skubal is the dream target, though the Dodgers and Mets are seen as favorites. Sonny Gray, a familiar name, is pitched as the realistic option. Chicago's $100M+ in expiring money gives room to at least make Skubal sweat. 💰
Jackson Cluff, a 29-year-old shortstop, retired Wednesday after eight minor-league seasons. He finished 2026 at Triple-A Iowa, hitting .148 in 18 games after the Cubs signed him in mid-August. A quiet exit, and no big-league time with the Cubs. 👋
A hypothetical Mason Miller trade could reportedly cost the Cubs top prospect Josiah Hartshorn plus more, with one proposal adding Jaxon Wiggins. Fixing the bullpen looks pricey, and Jed Hoyer would have to decide if Miller, controlled through 2029, is worth it.
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