Total contributions to super PACs: $30.9 million*
- $23.5 million to American Crossroads  (pro-Republican), including $3 million from Contran Corp.
- $2.3 million to Restore Our Future  (pro-Mitt Romney)
- $1.2 million to Red White and Blue Fund  (pro-Rick Santorum), all from his wife, Annette Simmons
- $1.1 million to Winning Our Future  (pro-Newt Gingrich)
- $1.1 million to the Texas Conservatives Fund (pro-David Dewhurst)
- $1 million to Make Us Great Again  (pro-Rick Perry), all from Contran Corp.
- $500,000 to Conservative Renewal (pro-Dewhurst)
- $100,000 to Restoring Prosperity Fund (pro-Perry, formerly Americans for Rick Perry)
- $50,000 to Strong Utah (pro-Orrin Hatch)
- $25,000 to Women Speak Out PAC (pro-Republican)
- $10,000 to Conservatives Acting Together (pro-conservative)
- $5,000 to Freedom PAC (pro-Connie Mack; pro-Allen West)
Notable federal hard money and 527 contributions:
- $2 million to Swift Boat Veterans for Truth (2004)
- $500,000 to Progress for America Voter Fund (2004)
- $2.9 million to American Issues Project (2008)
Notable state-level contributions:
- Simmons has donated  hundreds of thousands of dollars to Texas Attorney General Greg Abbott and Lt. Gov. David Dewhurst, plus more than $1 million to Republican Texas Gov. Rick Perry over the course of his political career.
Corporate ownership: Contran Corp.
Total spent on federal lobbying (2007-2012): $2.5 million, according to the Center for Responsive Politics .
Lobbying issues: Energy and nuclear power, hazardous and solid waste, environment and Superfund, real estate and land use, trade
Family: Wife Annette Simmons, daughters Scheryle Patigian, Lisa Epstein, Andrea Swanson and Serena Connelly, two other children
(Simmons died  on Dec. 28, 2013, after falling ill for several weeks.)
For a man worth more than $9 billion, Harold Simmons has had his share of problems. The owner of Contran Corp. nearly lost his fortune when his daughters sued him for control of the family’s wealth, and he has had to pay nearly $20,000 in fines for violating federal campaign contribution limits.
Simmons was born in 1931 in Golden, Texas, and graduated Phi Beta Kappa from the University of Texas at Austin. His first venture was the purchase of the University Pharmacy in Dallas. After 12 years, Simmons had turned one store into more than 100 and sold the chain to Eckerd for $50 million. Simmons was an early practitioner of the “leveraged buyout” — when an investor borrows heavily and takes an undervalued public company private and sells it for profit. He grew his fortune by buying and selling shares in a number of companies, including Amalgamated Sugar and Lockheed Corp.
In the mid-1990s, Simmons put all his wealth into trusts — ostensibly as a way to pass the wealth on to his children — but made himself the sole trustee, a decision criticized by legal experts interviewed by The New York Times . Simmons seemed to use the trust assets as his own and eventually ran into trouble with the Internal Revenue Service. As a result, his daughters, Andrea and Scheryle, filed a lawsuit against him in 1996. That lawsuit nearly cost him the fortune, according to the Times.
Simmons also ran into trouble with the Federal Election Commission in 1993 for violating the then-federal campaign contribution limit of $25,000 per year per individual, which resulted in him having to pay a $19,800 fine, according to FEC documents.
In addition to his super PAC giving, Simmons is a major contributor to conservatives’ campaigns, donating to Sen. Jon Kyl, R-Ariz.; Rep. Jeb Hensarling, R-Texas; Rep. Michele Bachmann, R-Minn.; and Sen. John McCain, R-Ariz., among others. He also gave $3 million to Swift Boat Veterans for Truth, the group whose ads helped sink Massachusetts Democratic Sen. John Kerry’s 2004 presidential campaign.
Most recently, Contran subsidiary NL Industries, a producer of the paint enhancer titanium dioxide, has been the subject of numerous lawsuits as a result of its environmental practices, according to D Magazine , a Dallas publication.
According to Forbes, the Texas House of Representatives approved a bill in 2011 that allowed Simmons’ Waste Control Specialists to transport low-level radioactive waste from other states and dispose of the material at its facility in Andrews County, Texas — an area that sits atop four aquifers. The review process that preceded the signing of the bill was lengthy and complicated, and D Magazine suggests it was influenced by Simmons’ donations to groups that supported Gov. Rick Perry.
Although Simmons' has given tens of millions of dollars to conservative political causes, the Dallas-based billionaire’s recent philanthropic giving has been anything but right-leaning, a Center for Public Integrity review  of Internal Revenue Service documents indicates.
The Harold Simmons Foundation in 2011 most notably contributed a combined $600,000 to an arch political foe of Republicans, Planned Parenthood, and its North Texas affiliate, IRS records show. It also donated to Public Campaign, a Washington, D.C.-based organization with a stated mission of working to “dramatically reduce the role of big special interest money in American politics.”
Last updated: Dec. 28, 2013
*2011-2012 election cycle. Source: Center for Responsive Politics and Center for Public Integrity analysis of Federal Election Commission records. Totals include contributions from individuals, family members and corporations that are controlled by the individual super donor.