The Antioch Baptist Church in Hillsboro, Tennessee is the largest church in the small town. Over 25% of the town's population of 30,000 inhabitants attends the church. As a result, the church and its minister, the Reverend Jeremiah Brown, have a lot of political sway.

The town is governed by a mayor and five city council members. The mayor and three of the city council members are members of the Antioch Baptist Church. The remaining two members are parishioners of St. Thomas More Catholic Church.

Reverend Brown recently discovered that his 16-year-old daughter had obtained several sex toys from a local store. He is outraged not only that such items are being sold to minors, but that they are being sold at all in Hillsboro. He was dismayed to find out that there is no current federal regulation of the sale of sex toys and that the State of Tennessee's sole regulation places a 5% tax on all sex toys sold in the state. He brings the lack of regulation to the attention of the mayor and City Council, who decide to pass a new law that reads:

City Ordinance 9.5.2014 A Law for the Preservation of Public Morals

Section 1: The preservation of the morality of the youth and citizens of the City of Hillsboro has been put in jeopardy by so-called 'sex toys.' This law is designed to prevent the distribution of such items to the citizens of this town.

Section 2: The sale, possession, or transportation of all sex toys in the town limits of Hillsboro is hereby prohibited, effective January 1st, 2020.

Section 2(a): A sex toy is defined as any instrument that can be used for the purpose of stimulating the human genitalia.

Section 2(b): This is a strict liability crime; knowledge of the nature of the item is not necessary for violation of this ordinance.

Section 2(c): Transportation includes all means and methods of delivery, whether by private individual or by courier service.

Section 3: Penalties

Section 3(1): Anyone caught selling a sex toy within the City of Hillsboro shall be punished with six months of imprisonment and a fine of not more than $10,000 per item sold.

Section 3(2): Anyone caught selling a sex toy within the City of Hillsboro to a person under the age of 18 shall be punished with one year of imprisonment and a fine of not less than $5,000 and not more than $20,000 per item sold.

Section 3(3): Anyone caught in possession of a sex toy within the City of Hillsboro shall be punished by up to six months of imprisonment and a fine of not more than $5,000 per item seized.

There is some grumbling among the town's population, but no one wants to admit that they possess such devices. However, the law is not without its detractors. Three groups have come forward to challenge the law in federal court.

The first is a local drug store owner, Bertram Cates. He arranged with the local police chief, Mort Meeker, to be arrested for selling a sex toy, a pair of edible underwear, in his store as a test case. He was convicted at a bench trial before Judge Mel Coffey and sentenced to 30 days of probation and a fine of $100. He has appealed his conviction under the law to the 5th Circuit Court of Appeals, claiming that the law is unconstitutional both as written and as applied in his case.

The second is a married couple of ten years, John and Jill Stebbins, who are residents of Hillsboro. They allege that they have always had an adventurous sex life, which has included the use of sex toys in the past. Although they have not been charged under the law, they claim that the very existence of the law has had a chilling effect on their sexual activities and is an unconstitutional violation of their rights.

The third is SallysSexySupplies.com, an internet retailer of sex toys based in Hollywood, California, which ships its products all over the United States. SallysSexySupplies.com alleges that 11% of their total sales come from the State of Tennessee. They further allege that the only way for them to not ship to Hillsboro would be to not ship to the entire State of Tennessee, as their tracking software does not make distinctions based on towns. They claim that the Hillsboro ordinance is an unconstitutional infringement on their business.

What are the best claims that each of the challengers can assert? Is each likely to succeed?