In 1914, Chase found conflict playing for the overbearing Charles Comiskey and got into an argument over his contract. A feature of many of Comiskey's contracts, and of other clubs at this time, was a "ten day clause," meaning the team could terminate a player's contract within ten days. Chase jumped the White Sox and played for Buffalo of the "outlaw" Federal League. Chase's explanation of his action was as follows: "At the time, Comiskey called me into his office and asked me to have the ten-day clause stricken from my contract. I demurred at this. A contract, it seemed to me, ought to bind both parties to the agreement. If that agreement allowed him to dispose of my services with ten days notice, I didn't see why I shouldn't enjoy the same privilege." The next month, Comiskey and the White Sox took Chase to the Supreme Court. In the second inning of a Buffalo game against Pittsburgh, Chase was served with an injunction. On July 9th, the White Sox and Hal squared off in court. Long before Curt Flood challenged baseball's reserve clause, Hal Chase found himself in the midst of a historic case against baseball ownership. Whether he was motivated out of selfishness or principle in fighting his contract, the judge in the case saw his point. The ruling in the case of the Chicago White Sox versus Hal Chase, as given by Judge Herbert Bissell, is as follows:

"While the services of these baseball players are ostensibly secured by voluntary contracts, a study of this system...reveals the involuntary character of the servitude which is imposed upon players by the strength of the combination controlling the labor of practically all of the players in this country. (This makes it) necessary for the player either to take the contract prescribed...or abandon baseball as a profession and seek some other livelihood... This system of servitude...provides for the purchase, sale, barter and exchange of the services of ball players, skilled laborers, without their consent ... (the players servitude) under the operations of this plan of agreement is contrary to the spirit of American institutions (and) to the spirit of the Constitution of the United States... This court will not assist in enforcing an agreement which is part of a general plan having for its object the maintenance of a monopoly, interference with the personal liberties of a citizen, and the control of his free right to labor wherever and for whom he pleases."