Holes in roofs, especially church roofs, appear as a motif throughout the story. The first such hole is found in the roof of the I Am My Brother’s Keeper Ministry in Detroit. Mitch Albom notices the 10-foot hole during his first visit to the church, but it is unclear how long it has been there. Since it is too costly to repair the roof, the church members simply place buckets under the hole to catch falling rain as necessary. However, the hole poses further problems, as it increases the cost of heating the building to the point that the utility company turns off the gas as the church falls further behind in their payments.

Albom learns of a different hole as he examines the Reb’s old sermons. This hole appeared in the roof of the synagogue in the 1970s, and the Reb’s sermon included an appeal for donations to patch the hole; presumably, the church received the funding it needed to make the repairs. Comparing the two experiences reveals differences between the two organizations, with Henry Covington’s ministry serving a poorer demographic. However, the coincidence also enables Albom to see a connection between the two churches for the first time,