http://slate.com/id/2123414/So, what do Roberts' investments say about him? He is rich, but not so rich that the $200,000 Supreme Court justice salary would feel like chump change. Still, he will be comfortable hobnobbing with other capitalists-turned-public servants in Washington (for whom $200,000 is chump change). Roberts benefits or will benefit from virtually all the various Bush tax cuts, from income to dividends to capital gains to estate taxes. His fortune is self-made, which suggests a bias toward self-reliance rather than entitlements and subsidies.
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Roberts' stock and mutual-fund holdings in 2003 were highly diversified, consisting of domestic and international stocks in multiple industries. In keeping with Roberts' reputation for prudence, the equities consisted primarily of dividend-paying blue chips like Coca Cola (less than $15,000), AT&T (less than $15,000, sold), Merck (less than $15,000), etc. Those who view Roberts as a robotic starched-shirt, however, should note evidence of a romantic-idealist streak: a chunk of XM Satellite Radio worth between $100,000 and $250,000. This bizarrely out-of-character investment suggests that Roberts is either clairvoyant or not afraid to dream: The stock is up tenfold since early 2003.
Also in keeping with Roberts' clean-cut, churchgoing image, his investments did not include companies in vice industries (gaming, drinking, smoking, etc.). If Roberts ascribes to the Peter Lynch-school of amateur investing—buy what you know—one might thereby infer that he is not a chain-smoking boozer who is forever sneaking off to Atlantic City. One might also conclude that he will instinctively frown on rulings that make life easier for gaming, smoking, and drinking companies (Wall Street take note!).
Roberts' stock portfolio is a conflict-of-interest nightmare. If Roberts continues to own all these stocks, he may have to recuse himself from many cases before the Supreme Court. (While in private practice in 2003, Roberts represented 19 states in their antitrust suit against Microsoft. Yet his 2003 financial disclosure form shows Roberts holding $100,000 to $250,000 worth of Microsoft stock.)
On the whole, Roberts' investment choices suggest that his financial character is much like his legal one. In investing, he tends to accept prevailing conventional wisdom—which, in the case of the financial markets, often changes and is often wrong—and to apply it with above-average competence.