If you look at the original census document for 1900 in Jefferson Twp. IN, the W for her middle initial could easily be read as an H.
Jessie W Mathews
United States Census, 1900
||Jessie W Mathews|
||Jeffersonville Township Jeffersonville city Ward 3, Clark, Indiana, United States|
|Relationship to Head of Household
|Relationship to Head of Household (Original)
|Number of Living Children
|Marriage Year (Estimated)
|Mother of how many children
|Jessie W Mathews
CITING THIS RECORD
"United States Census, 1900," database with images, FamilySearch(https://familysearch.org/ark:/61903/1:1:MMBN-3NY : accessed 12 May 2016), Jessie W Mathews in household of Homer Mathews, Jeffersonville Township Jeffersonville city Ward 3, Clark, Indiana, United States; citing sheet 4B, family 85, NARA microfilm publication T623 (Washington, D.C.: National Archives and Records Administration, n.d.); FHL microfilm 1,240,363.