The Unadilla Valley Railway Company v. Caldine, Administrator case in 1928 involved a dispute over the liability of damages caused by an accident on the railway. The plaintiff was seeking compensation for injuries sustained when his car collided with one of the defendant's trains at a crossing. The Supreme Court ruled that under New York law, which applied to this case, it is not necessary for a railroad company to maintain constant watchmen or signals at every highway crossing along its line as part of its duty towards travelers on highways; rather, what constitutes reasonable care depends upon circumstances and conditions including location and frequency of use among others. Therefore, failure to provide such safeguards does not automatically constitute negligence unless it can be shown that due diligence required them under particular circumstances.

The dissenting opinion in the case of Unadilla Valley Railway Company v. Caldine, 1928, argued that the majority's decision to uphold a New York law allowing for double damages against railroads was incorrect. The dissenting justices believed that this law unfairly singled out railroad companies and placed an undue burden on them compared to other types of businesses. They contended that such laws should be considered unconstitutional as they violate the Equal Protection Clause by creating arbitrary and unreasonable classifications among different types of businesses. Furthermore, they disagreed with the majority's interpretation of precedent cases involving similar issues, arguing instead that these past decisions supported their view that discriminatory laws like this one are not permissible under the Constitution.