In the case of Chessman v. Teets, Warden in 1956, Caryl Chessman was convicted for robbery, kidnapping and rape under California's "Little Lindbergh Law," which made kidnapping with bodily harm a capital offense. The U.S Supreme Court reviewed whether his constitutional rights were violated due to lack of counsel during police interrogation and trial proceedings. It also examined if there was any violation in terms of self-representation as he had represented himself at trial without adequate legal knowledge or experience. Furthermore, it considered whether the application of the “Little Lindbergh Law” itself constituted cruel and unusual punishment under Eighth Amendment grounds given that no death occurred during the crime committed by Chessman. The court upheld his conviction ruling that there was no constitutional right to counsel during police interrogations at that time (a precedent later overturned by Miranda v Arizona). They found no issue with him representing himself since he knowingly waived his right to an attorney despite being warned about potential consequences. Lastly, they ruled applying Little Lindbergh law did not constitute cruel or unusual punishment because severity of penalty is largely left up to states' discretion unless it involves torturous methods explicitly banned by constitution.

In the dissenting opinion for Chessman v. Teets, Justice William O. Douglas argued that Caryl Chessman's constitutional rights were violated during his trial and subsequent conviction in California state court. He believed that the defendant was denied a fair trial because he did not have legal representation when he needed it most - during police interrogation and at critical stages of his pre-trial proceedings. Moreover, Douglas pointed out that there was no stenographic record of what transpired before the grand jury which indicted him, thus making it impossible to determine whether or not prosecutorial misconduct occurred during those proceedings. Furthermore, Justice Douglas criticized the majority for failing to address these issues adequately in their decision upholding Chessman's conviction and death sentence.