Wolff is only the second person to serve as both San Antonio mayor and county judge of Bexar County. Since 1989, Wolff has been married to his second spouse, the former Tracy Hoag. He has four children from the first marriage to Melinda Wolf: Kevin Alan, Lyn Marie, Scott, and Matthew. He has two stepchildren through the second marriage. His oldest son from his first marriage, Kevin Wolff, a Republican, serves with his father on the Bexar County Commissioners' Court as the Precinct 3 commissioner. 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. Wolff is working with the commissioners court to restore the former Hot Wells hotel, spa, and bathhouses, which flourished in the first two decades of the 20th century, along the San Antonio River in the southside of San Antonio. In October 2015, the commissioners authorized $4 million to begin the partial restoration of the facility, which once attracted celebrities from throughout the nation. Wolff is interested in baseball, poker, cigars, and is a lifelong reader with an extensive collection of books. 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. He is a graduate of St. Mary's University and St. Mary's University School of Law, both in San Antonio. Wolff has penned four 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 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. In 2017, Wolff rose to defend his friend Ricardo Romo, who after eighteen years of service resigned as president of the University of Texas at San Antonio amid reports that Romo had inappropriately hugged and embraced women on campus who he greeted. Wolff claims that the University of Texas System mishandled the investigation into Romo's conduct. Wolff said that he too often embraces men and women in the workplace: "It's a tradition in the Hispanic community that you do that.... It's just a tradition, one I participate." The Nelson W. Wolff Municipal Stadium, home field of the San Antonio Missions located off U.S. Highway 90 near the intersection with State Highway 151, is named in his honor.
