In his Winter Meetings media session, David Ross was asked if he believes the Cubs can win right now. Without hesitation, Ross confirmed he thinks this roster can and will compete. Host David Kaplan, Gordon Wittenmyer, and Maddie Lee discuss if the Cubs can retool and win at the same time or if Ross is doing coach speak. The group also discusses Anthony Rizzo's future as a Cub. Later, following MLB reclassifying the Negro Leagues a major league, Bob Kendrick, president of the Negro Leagues Baseball Museum, joins the podcast. Kendrick discusses his hesitant reaction to the news and what this means for the history of the Negro Leagues.(2:50) - Does David Ross truly believe he can win with this roster?(6:30) - Does being in a down division help the Cubs believe they can still win?(13:39) - With Anthony Rizzo in the final year of his contract, will the Cubs extend him?(17:55) - Bob Kendrick, president of the Negro League Baseball Museum, joins Gordon Wittenmyer and Maddie Lee(19:00) - Kendrick discusses his reaction to the news and its significance(29:30) - Minnie Minoso was the Latino Jackie Robinson(36:15) - The Pirates and the Cleveland Indians could have had Black players but all declined