https://northsidebaseball.com/videos/chicago-cubs/page/2/?d=3Chicago Cubs Videos: Chicago Cubs Videosenhttps://northsidebaseball.com/videos/chicago-cubs/why-the-cubs-got-a-steal-in-jacob-webb-r270/The Chicago Cubs signed veteran right-handed reliever Jacob Webb to a 1-year, $1.5 million deal with a club option in 2027. Here's a deeper look at how the 32-year-old is only getting craftier with time despite not having high velocity or strikeout rates.270Fri, 26 Dec 2025 14:39:00 +0000https://northsidebaseball.com/videos/chicago-cubs/5-cubs-prospects-ready-to-explode-in-2026-r269/Here are five Cubs prospects who are destined to break into the major leagues, with or without the team, in the coming year. Cory Sparks dives into the strengths, weaknesses, and fit of Jaxon Wiggins, Ethan Conrad, Jonathon Long, Grant Kipp, and James Triantos.269Mon, 22 Dec 2025 14:15:00 +0000https://northsidebaseball.com/videos/chicago-cubs/cubs-continue-hunting-small-signing-caleb-thielbar-tyler-austin-r268/The Chicago Cubs' quiet offseason continues, as the team made two more savvy signings in Caleb Thielbar and Tyler Austin while waiting out the top end of the free-agent market.268Fri, 19 Dec 2025 14:55:00 +0000https://northsidebaseball.com/videos/chicago-cubs/winter-meetings-review-all-quiet-on-the-midwestern-front-r267/The Chicago Cubs didn't do much at the Winter Meetings, but as their signing of reliever Hoby Milner proves, they're clearly planning to be active throughout the rest of the offseason.267Fri, 12 Dec 2025 14:46:02 +0000https://northsidebaseball.com/videos/chicago-cubs/phil-maton-is-a-good-start-but-cubs-bullpen-overhaul-has-only-just-begun-r266/The Chicago Cubs wisely scooped up strikeout artist Phil Maton for their depleted bullpen, but their need for velocity and more relievers still stands out like a sore thumb on the roster.266Tue, 02 Dec 2025 14:45:01 +0000https://northsidebaseball.com/videos/chicago-cubs/what-cubs-fans-are-thankful-for-this-thanksgiving-r265/It's that time of year again! North Side Baseball invites you to discuss your favorite players and moments from the 2025 Chicago Cubs season!265Wed, 26 Nov 2025 14:48:02 +0000https://northsidebaseball.com/videos/chicago-cubs/dream-cubs-free-agent-acquisitions-for-2025-2026-offseason-r264/As the Chicago Cubs plot their course for the offseason, which free agent and trade targets should they prioritize pursuing? How would Dylan Cease or MacKenzie Gore look at the top of the rotation? Would Bo Bichette be a fit in the infield? How about Steven Kwan roaming the outfield?264Tue, 18 Nov 2025 14:57:00 +0000https://northsidebaseball.com/videos/chicago-cubs/cubs-rumors-shota-imanaga-pitching-upgrades-franchise-direction-r263/The Chicago Cubs sit on the precipice of their most important offseason in a decade, though their commitment to the short-term window remains a genuine question.263Fri, 14 Nov 2025 14:47:01 +0000https://northsidebaseball.com/videos/chicago-cubs/3-cubs-win-gold-gloves-certifying-status-as-elite-defensive-team-r262/Nico Hoerner, Ian Happ, and Pete Crow-Armstrong brought home Gold Gloves for their defensive efforts in 2025, as the Cubs were rewarded for their conscious decision to build a defense-first team.262Thu, 06 Nov 2025 14:49:00 +0000https://northsidebaseball.com/videos/chicago-cubs/shota-imanaga-shown-the-door-andrew-kittredge-sent-packing-r261/The Chicago Cubs executed a pair of cost-cutting maneuvers with their pitching staff by declining the option of Shota Imanaga and trading Andrew Kittredge, leaving questions about their desire to seriously compete in 2026.261Wed, 05 Nov 2025 14:44:00 +0000https://northsidebaseball.com/videos/chicago-cubs/cubs-2025-season-eulogy-brewers-end-world-series-hopes-r260/After staging an impressive NLDS comeback, the Cubs fell flat in Game 5 against the Brewers. With so many offseason questions awaiting them, what can Chicago learn from the 2025 season?260Tue, 14 Oct 2025 13:29:58 +0000https://northsidebaseball.com/videos/chicago-cubs/cubs-shutout-brewers-putting-nlds-in-sudden-death-territory-r259/Behind Matthew Boyd and brilliant pitching from the bullpen, the Cubs leveled the NLDS with the Brewers. Who has the advantage heading into the winner-takes-all Game 5?259Fri, 10 Oct 2025 22:43:02 +0000https://northsidebaseball.com/videos/chicago-cubs/cubs-exhaust-bullpen-to-win-game-3-whats-left-for-game-4-r258/The Chicago Cubs barely escaped with a victory over the Milwaukee Brewers in Game 3 of the NLDS, having to use their hottest starting pitcher and all of their high-leverage relievers to do so. With Freddy Peralta slated to start Game 4, are the Cubs still on the ropes?258Thu, 09 Oct 2025 13:27:11 +0000https://northsidebaseball.com/videos/chicago-cubs/brewers-demoralize-cubs-in-game-2-setting-stage-for-elimination-games-r257/Behind some impressive home runs and elite velocity, the Milwaukee Brewers have taken commanding control of the NLDS, putting the Chicago Cubs on the brink of elimination.257Wed, 08 Oct 2025 13:47:01 +0000https://northsidebaseball.com/videos/chicago-cubs/cubs-prospect-of-the-year-owen-caissie-r256/In a talented Cubs farm system, Owen Caissie was the most impressive prospect. A look at what made him the prospect of the year for the Cubs.256Tue, 07 Oct 2025 13:58:00 +0000https://northsidebaseball.com/videos/chicago-cubs/will-brewers-game-1-plan-make-cubs-overthink-game-2-r255/The Milwaukee Brewers jumped out to a commanding lead in the early innings of a Game 1 NLDS victory, putting the Cubs on notice after they burned through some of their most important bullpen arms.255Mon, 06 Oct 2025 17:53:32 +0000https://northsidebaseball.com/videos/chicago-cubs/craig-counsell-pat-murphys-chess-match-reaches-fever-pitch-r254/Following their Wild Card Round win over the San Diego Padres, the Chicago Cubs are set to face their division rival, the Milwaukee Brewers, for the right to play for the NL pennant.254Fri, 03 Oct 2025 22:49:01 +0000https://northsidebaseball.com/videos/chicago-cubs/cubs-slide-past-padres-behind-stellar-middle-infield-r253/Thanks to some sterling middle-infield defense (and a generous strike three call in the ninth inning), the Cubs barely outlasted the Padres in a tense Wild Card series.253Fri, 03 Oct 2025 13:46:01 +0000https://northsidebaseball.com/videos/chicago-cubs/cubs-stymied-by-padres-pitching-setting-up-sudden-death-game-3-r252/A high-flying act by the Padres' pitching staff completely stifled the Cubs' offense, leaving Yu Darvish and Jameson Taillon as the final defenders of their teams' respective seasons.252Thu, 02 Oct 2025 13:48:01 +0000https://northsidebaseball.com/videos/chicago-cubs/cubs-shut-down-padres-in-game-1-set-bullpen-opener-for-game-2-r251/The Chicago Cubs have put the San Diego Padres on the brink of elimination, though their pitching plans for the remainder of the series don't scream confidence.251Wed, 01 Oct 2025 13:41:01 +0000https://northsidebaseball.com/videos/chicago-cubs/previewing-the-cubs-wild-card-matchup-against-the-padres-r250/The Cubs and Padres are set to square off in a best-of-three Wild Card series matchup at Wrigley Field. Which team is favored, and how can the underdog pull off the upset?250Sat, 27 Sep 2025 13:42:01 +0000https://northsidebaseball.com/videos/chicago-cubs/kyle-tuckers-mysterious-calf-injury-could-doom-cubs-playoff-hopes-r249/Kyle Tucker is removing himself from the team as he attempts to rehab from his lingering calf issue. Is there a legitimate reason to be concerned about his health just two weeks out from the playoffs?249Mon, 22 Sep 2025 13:43:02 +0000https://northsidebaseball.com/videos/chicago-cubs/cubs-clinch-playoff-spot-on-verge-of-securing-1st-wild-card-spot-r248/The Chicago Cubs finally secured their playoff spot by sweeping the Pirates, locking in their first October appearance since 2020. Can they ensure the Wild Card Round is hosted in Wrigley Field?248Sat, 20 Sep 2025 13:46:01 +0000https://northsidebaseball.com/videos/chicago-cubs/cubs-state-of-the-union-october-nears-as-division-slips-out-of-reach-r247/What do Cubs fans have to look forward to in the final few weeks of the regular season?247Fri, 12 Sep 2025 13:37:56 +0000https://northsidebaseball.com/videos/chicago-cubs/anthony-rizzo-retires-as-a-cub-evoking-fond-memories-of-better-times-r246/Legendary Cubs first baseman Anthony Rizzo has returned to the franchise to retire. What are some of the best moments of his tenure in Chicago?246Thu, 11 Sep 2025 13:28:55 +0000https://northsidebaseball.com/videos/chicago-cubs/who-will-be-the-cubs-game-one-starter-in-the-playoffs-r245/The Cubs have three viable options to serve as their ace for the postseason. Will Cade Horton, Matthew Boyd, or Shota Imanaga get the nod to start Game One?245Sat, 06 Sep 2025 13:48:02 +0000https://northsidebaseball.com/videos/chicago-cubs/cubs-shuffle-roster-for-september-add-carlos-santana-white-sox-castoff-r244/The Cubs' front office made up for a weak trade deadline by making a number of moves to close out September, including adding Carlos Santana and Aaron Civale.244Fri, 05 Sep 2025 14:34:00 +0000https://northsidebaseball.com/videos/chicago-cubs/what-were-excited-for-and-nervous-about-before-cubs-playoff-run-r243/With the Cubs coming up on their first playoff run since 2020, what about the team is making fans nervous, and what is worth getting excited about?243Thu, 28 Aug 2025 15:10:01 +0000https://northsidebaseball.com/videos/chicago-cubs/kyle-tucker-sitting-for-brewers-series-pushing-owen-caissie-into-the-spotlight-r242/Kyle Tucker will finally rest his finger injury... against the Brewers, of all teams. Can Owen Caissie fill such big shoes?242Thu, 21 Aug 2025 13:49:01 +0000https://northsidebaseball.com/videos/chicago-cubs/cubs-land-4-prospects-on-mlb-pipelines-midseason-list-r241/The Cubs saw a big change to their top prospect list in the mid-season update, with three new members joining Owen Caissie in the Top 100.241Fri, 15 Aug 2025 13:46:01 +0000