Just looking at baseball-reference’s 1997 Cubs team page, you’d never think that team could lose 14 straight. Sammy Sosa, Mark Grace, Ryne Sandberg, Shawon Dunston... guys who played for the Cubs in multiple postseasons.
Of course, Sandberg was in his final season and Sosa wasn’t yet the 60-homer guy he became the following year. And the pitching staff was atrocious, especially closer Mel Rojas, who had six blown saves by the end of July. The miracle was that the Cubs actually found someone to take him off their hands in a trade that proved important for the 1998 Cubs wild-card team.