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Cliff may have failed criminal law, but even he knows that Logan Echolls won't impress anyone with a poor-little-rich-boy routine. He prefers defending his usual stripper and biker gang clientele to representing smug and stupid rich boys like Logan. Trading slightly unethical favors with Veronica Mars and helping out the helpless tawdry like Loretta Cancun, Cliff serves the dark underbelly of Neptune. He supported Keith Mars in his failed bid to be Neptune's sheriff, even though Keith becoming sheriff might have been bad for business. Underneath that cynical exterior must lie a heart of gold.
Or a sultry loverboy! Cliff went and got himself hooked up with a lady doc escort, one who happened to steal his briefcase. And his heart? While extricating himself from the mess took Keith's help and not a little embarrassment, Cliff handled it with his usual aplomb. Even with no pants on, the man's got style. Unfortunately, he's also got missing case files and stolen keys to the Echolls storage locker. D'oh!