Our Dream MLB Playoff Matchups (with Jolly Olive)

Go to kushydreams.com and use Promo Code JOMBOY at checkout to get 20% off your next order!++++++++++++Timestamps:0:00 Jolly Olive is Here1:25 Daydreaming About October3:20 Setting the Stage5:15 Yankees vs. Red Sox10:55 Astros vs. Rangers OR Mariners16:35 What's the Top Three?20:15 Dodgers vs. Padres23:40 Brewers vs. Cubs29:35 Mets vs. Phillies and Mets vs. Brewers30:45 Phillies vs. Dodgers34:45 Favorite World Series Matchups35:35 Mariners vs. Brewers or Padres37:45 Yankees vs. Mets39:45 Phillies vs. Astros Rematch44:10 Top Three Matchups

Go to kushydreams.com and use Promo Code JOMBOY at checkout to get 20% off your next order!++++++Timestamps:0:00 All-Time Episode on the Way  3:50 First Base9:20 Second Base  14:00 Shortstop18:50 Third Base25:30 Outfielders55:35 Utility1:00:45 Jason Kendall  1:02:10 Dontrelle Willis  1:03:40 Yusmeiro Petit1:10:50 El Duque  1:15:35 Eddie Guardado  1:17: Benito Santiago 

Read Jim Bowden's article alongside us: https://www.nytimes.com/athletic/6577911/2025/08/27/mlb-playoff-contenders-concerns-questions/Go to kushydreams.com and use Promo Code JOMBOY at checkout to get 20% off your next order!Connect with a provider at http://ro.co/wakenjake to find out if prescription Ro Sparks are right for you!Download the DraftKings Sportsbook app and use promo code JMBASEBALLGAMBLING PROBLEM? CALL 1-800-GAMBLER, (800) 327-5050 or visit gamblinghelplinema.org (MA). Call 877-8-HOPENY/text HOPENY (467369) (NY). Please Gamble Responsibly. 888-789-7777/visit ccpg.org (CT) or visit www.mdgamblinghelp.org (MD). 21+ and present in most states. (18+ DC/KY/NH/WY). Void in ONT/OR/NH. Eligibility restrictions apply. On behalf of Boot Hill Casino & Resort (KS). 1 per new customer. $5+ first-time bet req. Max. $300 issued as non-withdrawable Bonus Bets that expire in 7 days (168 hours). Stake removed from payout. Terms: sportsbook.draftkings.com/promos. Ends 9/7/25 at 11:59 PM ET. Sponsored by DK.++++Timestamps:0:00 Intro1:15 Jolly Olive  2:30 New York Yankees Defense (Volpe) and Facing Winning Teams  7:20 Fried & Rodon Haven't Been Their Best and are Both Left Handed  10:10 Seattle Mariners  11:20 Realignment Theories and Stats  15:55 Are the Mariners Too Right-Handed?18:00 Boston Red Sox Rotation Depth  21:50 Houston Astros vs. Health  25:40 Toronto Blue Jays Bullpen & Inexperience28:55 Detroit Tigers Not Being Pushed Down the Stretch  32:50 Reds Probably Won't Even Make the Playoffs  33:55 Mets Bridge to Edwin Diaz and Lineup Depth  38:50 San Diego Padres Starting Rotation  41:20 Kyle Tucker's Slump & Chicago Cubs Pitchers  44:05 LA Dodgers vs. Health, Bullpen, and the Pressure  47:55 Philadelphia Phillies Lost Zack Wheeler  50:40 Milwaukee Brewers Lack of Power 

Go to kushydreams.com and use Promo Code JOMBOY at checkout to get 20% off your next order!Get $10 Off @BRUNT with code BAKERS at https://bruntworkwear.com/BAKERS! #bruntpod #sponsored++++++Timestamps:0:00 Thanks for Last Ep!2:10 Yanks-Red Sox This Weekend3:45 My Fake Goatee  4:55 Trade Deadline Check-In  7:10 Biggest Second Halves So Far  12:55 Orioles Have Pitching!15:30 Blue Jays Pitching is Nuts  19:15 Biggest Hitters  20:00 The A's (Nick Kurtz)  24:45 Top 5 in Homers  30:00 Michael Harris II  31:35 Colson Montgomery34:30 Ramon Laureano 

Go to kushydreams.com and use Promo Code JOMBOY at checkout to get 20% off your next order!Tackle your to-do list today and get 15% off your first task at https://taskrabbit.com or on the Taskrabbit app using promo code BAKERS.++++Timestamps:0:00 Manfred Spoke  6:25 Expansion Draft Would Be Delicious  16:35 Where Will the New Teams Be?37:25 Realigning the Divisions

Wake n Jake dives deep into why the 2025 Milwaukee Brewers are dominating MLB—with the best record in baseball, electric pitching, and an 11-game win streak—yet are still under the radar as World Series contenders. How can a team this good not have a single player in ESPN’s Top 50? We’ll break down the Brewers’ winning formula, the stars flying below the radar, and why Milwaukee’s overlooked squad could be October’s biggest surprise. Don’t miss this full Brewers breakdown—like, comment and subscribe for more sharp MLB insights!Go to kushydreams.com and use Promo Code JOMBOY at checkout to get 20% off your next order!  

Go to kushydreams.com and use Promo Code JOMBOY at checkout to get 20% off your next order!Download the DraftKings Sportsbook app and use promo code JMSPORTSGAMBLING PROBLEM? CALL 1-800-GAMBLER, (800) 327-5050 or visit gamblinghelplinema.org (MA). Call 877-8-HOPENY/text HOPENY (467369) (NY). Please Gamble Responsibly. 888-789-7777/visit ccpg.org (CT) or visit www.mdgamblinghelp.org (MD). 21+ and present in most states. (18+ DC/KY/NH/WY). Void in ONT/OR/NH. Eligibility restrictions apply. On behalf of Boot Hill Casino & Resort (KS). 1 per new customer. $5+ first-time bet req. Max. $200 issued as non-withdrawable Bonus Bets that expire in 7 days (168 hours). Stake removed from payout. Terms: sportsbook.draftkings.com/promos. Ends 9/29/25 at 11:59 PM ET. Sponsored by DK.+++++Timestamps:0:00 New York Teams Struggling  1:25 Detroit Tigers Last Year  3:45 One Thing I Don't Like About San Diego  4:45 Diamondbacks  5:40 Braves  6:10 Cubs7:45 Reds  8:53 Rockies9:40 Dodgers11:15 Marlins  12:15 Brewers13:30 Mets14:25 Phillies15:45 Pirates  16:30 Padres17:10 Giants17:55 Cardinals18:40 Nationals  20:50 Athletics22:12 Orioles23:00 Red Sox24:05 White Sox  24:40 Guardians26:18 Tigers27:25 Astros  28:53 Royals30:00 Angels31:08 Twins32:15 Yankees33:35 Mariners  35:03 Rays35:58 Rangers36:40 Blue Jays  37:55 Excited for the Home Stretch of the Season38:40 My San Diego Fantasy Football Draft Weekend 

Go to kushydreams.com and use Promo Code JOMBOY at checkout to get 20% off your next order!+++++0:00 Yankees Have Been Awful47:20 The Rest of MLB  48:30 Fantasy Football Plans 

Grade every winner and loser from the wild 2025 MLB trade deadline with Talkin’ Jake and Foolish Baseball! We’re breaking down which teams dominated, who missed out, and stacking them all on a TIER LIST. From blockbuster moves to surprising sellers and playoff shakeups, get quick reactions, in-depth analysis, and spicy takes on every deal that rocked baseball.Go to kushydreams.com and use Promo Code JOMBOY at checkout to get 20% off your next order!Get $10 Off @BRUNT with code BAKERS at https://bruntworkwear.com/BAKERS! #bruntpod #sponsored+++++Timestamps: Timestamps:  0:00 Winners and Losers of the Trade Deadline4:10 Houston Astros10:00 Yankees13:00 A's17:40 Padres23:05 Braves  28:20 Speedway Classic29:20 Pirates  33:50 Tigers  37:00 Mets-Phillies Arms Race  39:25 Brewers42:15 Mariners45:30 Dodgers  48:55 Diamondbacks51:55 Rangers54:20 What Was This Category57:35 Cubs and Reds  1:02:05 Orioles  1:03:25 Boston Red Sox  1:06:00 Cleveland & Colorado  1:09:15 Royals  1:10:35 Miami Marlins  1:12:10 Twins  1:15:00 Giants1:16:25 Rays  1:17:20 Blue Jays  1:18:40 Nationals 

Go to kushydreams.com and use Promo Code JOMBOY at checkout to get 20% off your next order!++++++Timestamps:  0:00 Intro  1:55 Not Letting the Braves Hurt Us  4:15 Yankees Trade for Shane Bieber  17:30 Padres Trade for Marcell Ozuna  29:50 Reds Trade for ??????39:50 Phillies Trade for David Bednar  53:40 Tigers Trade for Eugenio Suarez