Wolff is only the second person to serve as both San Antonio mayor and county judge of Bexar County.[6] (The first was Bryan Callaghan, Jr., who became mayor in 1885 and county judge in 1892.)[7]
With his late father and two brothers, he owned several businesses, most notably Sun Harvest Farms grocery stores and Green Fields Market, a health foods and organic grocery store in San Antonio, which Wolff sold in 2011.
Wolff has penned five books. In Challenge of Change, he describes his experience in the Texas legislature and his participation in the 1974 Constitutional Convention, of which he was instrumental in bringing about. In Baseball for Real Men, Wolff reflects on life and his love of the game. Mayor is a memoir of San Antonio politics focusing on his time in City Hall. In Transforming San Antonio (Trinity University Press) Wolff gives an insider's view on signature economic-development projects with which he was involved: the AT&T Center, a Toyota factory, the PGA Village, and the extension of the San Antonio River Walk. He also authored the book 95 Power Principles: Strategies for Effective Leadership in Government, which documents the lessons learned over his decades in public service and in business.[8]
Wolff was initially appointed to this current position in 2001 to succeed Cyndi Taylor Krier, a Republican, who resigned to accept an appointment from then Governor Rick Perry as a regent of the University of Texas System. Wolff has since been elected to this position three times. In January 2012, he announced that he would seek a fourth full term in 2014.[9] He defeated in the general election the Republican candidate, Carlton L. Soules, a former member of the San Antonio City Council from the North Side. Known as a "budget hawk" while on the council, Soules since entered into an alliance with the unsuccessful 2017 San Antonio mayoral candidate Manuel Medina, the chairman of the Bexar County Democratic Party organization. The two had opposed a defunct a downtown street car project, which they considered a "boondoggle."[10]
Wolff won re-election as county judge in the general election held on November 6, 2018. He defeated the Republican nominee, Probate Judge Tom Rickhoff.
In October 2021, Wolff announced that he would not seek re-election for the position of county judge.[11]
Personal life
Since 1989, Wolff has been married to his second spouse, the former Tracy Hoag. He has four children from the first marriage to Melinda Wolff: Kevin Alan, Lyn Marie, Scott, and Matthew. He has two stepchildren through the second marriage. His oldest son from his first marriage, Kevin Wolff (born c. 1965), a Republican, served with his father on the Bexar County Commissioners' Court as the Precinct three commissioner until 2021. The two disagreed over a downtown streetcar plan favored by the father and adamantly opposed by the son. They agreed on a proposal to build a rail system with the use of eighteen miles of existing Union Pacific track from downtown San Antonio to Leon Springs.[12]
^Wolff, Nelson W. Transforming San Antonio: An Insiders View of the AT&T Center, Toyota, the PGA Village, and the River Walk Extension., Trinity University Press, 2008