Another one of McGraw's reclamation projects, Raymond had a reputation as one of the hardest players to manage in the NL. McGraw was able to coax one great season out of him, as he went 18-12 after being obtained from St.Louis, where he had a 2.03 ERA in 1908, and led the NL in losses with 25. Christy Mathewson once said, "after a night out, don't get too close to Bugs, his breath will stop a freight train".
Bugs also had a bit of a temper too. He liked to do things his way. If he wanted to stay out late, he was "gonna stay out late". McGraw made every attempt to save the man, priding in himself that he could turn Raymond around. Axed midway through the 1911 season, he returned to his hometown of Chicago. He did a little pitching and some umpiring in semi-pro circles.
On Saturday, September 7th, 1912, Raymond was found dead in a hotel room. Originally a heart attack was given as the cause of death, but after some investigation by authorities, it was discovered that he had a fractured skull and died of a cerebral hemorrhage. Chicago native Frank Cigrans confessed that he had gotten into an argument with Raymond at a baseball game several days earlier. The argument escalated into a fight, Cigrans pummeling Raymond about the head. It was later revealed that Raymond himself had gotten into a brawl with several men three weeks earlier and had been rapped in the head several times with a baseball bat. This compounded with the beating he took from Cigrans, and the late night partying, may have led to his untimely demise. When news of his death reached McGraw, "Little Napoleon" snapped, "that man took 7 years off my life". I guess you could say, they didn't nickname him Bugs for nothing.