Political devil. The Judas Iscariot of Oregon politics. Little Napoleon. Those are among the terms used to describe Joseph Simon, the nation’s first Jewish Republican senator. Oregon’s Boss Simon was a machine politician who hobnobbed with U.S. presidents. But he had an ugly falling out with Teddy Roosevelt, accusing the president of discriminating against him because he was Jewish. The author had heard about his famous relative. But no one in the family knew much about Senator Simon. So, Richard Simon, a former congressional correspondent for the Los Angeles Times, looked into Senator Simon’s life. What he discovered was a man described as ?worse than a Southern Pacific train robber.? Joe Simon’s election to the U.S. Senate was called ?one of the greatest political surprises ever. Simon, an attorney for powerful railroads, played a critical role in the development of the Pacific Northwest.