Mayor Eric Adams says he was not bribed when Turkish citizens gifted him more than $100,000 in business class airline tickets, luxurious hotel suites and luxury nights in the city of Istanbul.

Federal prosecutors disagree. They say the glamorous travel perks were bribes Adams accepted in exchange for pressuring FDNY officials to allow a new Turkish consulate to open before the building could pass a security inspection.

On Friday, both sides will present their arguments in court in the first major hearing in Adams’ case. federal corruption case. The mayor’s lawyers ask a judge to throw the bribery charge in his five-count indictment.

Adams’ argument hinges on some recent U.S. Supreme Court cases that legal experts say have made it harder to convict people on federal corruption charges. A judge will have to decide whether the flight enhancements were illegal or simply unpleasant. Legal experts say it largely comes down to one key question: Were the gifts a gratuity (a token of appreciation without any prior agreement) or was there a “quid pro quo” (an agreement to exchange gifts for influence)? In many cases, they say, the line is blurry.

So how can Gothamist readers know if the gift cards, gold bars, wads of cash, or free international flight upgrades they may be offered are bribes or gratuities under federal law? We used some hypothetical and real-life examples to make this quiz.

A gift card to a steakhouse

Mrs. Munee has a student named Bill in her 11th grade AP English class who has really been struggling with his homework. He meets with Bill’s parents, who say they are worried about his grades because he is about to apply to colleges and needs to impress admissions officers. A week later, Bill earns his first “A” on a paper in Mrs. Munee’s class and the high grades continue for the rest of the school year. After Bill earns an “A” on his report card and is accepted into a prestigious college, his parents give Mrs. Munee a $100 gift card to the best steakhouse in town.

If Bill’s parents never offered to give Ms. Munee a gift in advance and the teacher didn’t change the grade in hopes of receiving one, it would probably be considered a bonus, said Richard Briffault, a professor at the Law School. Columbia teaching A course on public corruption. He said that perhaps the teacher determined that Bill deserved more credit for his efforts.

But the calculus could change if, in their meeting with Ms. Munee, Bill’s parents asked the teacher to improve their son’s grade and told her, “We’ll make it worth it,” said attorney Michael Feldberg, who represented the former state Assembly. President Sheldon Silver at his 2018 corruption trial. If that statement influenced Ms. Munee to change the rating, she said, “it would probably make it look more like a bribe.”

A check for $13,000

A small Midwestern town needs new garbage trucks and Mayor Gold has to choose a company for the contract. Choose a dealer and authorize the city to pay the company more than $1 million for five trucks. The truck dealer is elated. Several months later, the owner sends Mayor Gold a check for $13,000. The mayor says this payment is for “consulting services” he provided to the company.

This scenario is actually based on a recent decision by the United States Supreme Court. James Snyder, mayor of Portage, Indiana, accepted the check and was charged with accepting an illegal gratuity. In June, judges ruled that it had not violated federal law.

Judge Brett Kavanaugh said that federal law it is not clear. He added that if the above scenario were banned, it could make it nearly impossible for mail carriers and public school teachers to know whether they can accept gifts like holiday tips or tickets to basketball games without risking violating federal law. However, under that decision, the mayor’s $13,000 check is also technically legal.

“The government’s purported guidance would leave state and local officials completely at sea to guess what gifts they can accept under federal law, with the threat of up to 10 years in federal prison if they guess wrong,” Kavanaugh wrote.

But while the decision was intended to clarify what types of gifts are illegal, some experts have warned it could lead to even more confusion.

“It’s a disaster. It’s complex. The distinctions are difficult to follow,” Feldberg said. “Every time a case comes to court and the court fights with it, let’s put it this way: I don’t think they’re making it any clearer.”

Daniel Weiner, director of the Brennan Center’s Government and Elections Program, said the ruling does not deem tipping “A-OK,” but it does mean it is not criminal under federal law.

“The Snyder case could potentially lead to freedom for all,” he said. “As long as you refrain from having any type of explicit agreement before engaging in corrupt activities, then you have potentially insulated yourself from the reach of federal corruption law.”

A luxury penthouse

Councilman Slots represents a neighborhood where a powerful real estate developer wants to open a casino inside a new luxury housing and shopping complex. Many longtime residents don’t want a casino in their community and fear the luxury development could drive up their rents. Councilman Slots agrees and openly opposes the plan.

But then the developer asks to meet with her and, over dinner, promises that this development will make her life “so much better.” The next morning, Councilwoman Slots announces her support for the redevelopment plan. It also casts a deciding vote at City Council to approve the plan. When the luxury condos are completed two years later, the developer offers the penthouse to Councilman Slots at a greatly reduced price.

If the developer asked Councilman Slots to support the casino plan and offer benefits in exchange, Feldberg said, the official would likely be in danger of a bribery charge.

“That sounds like a quid pro quo to me,” he said.

But Feldberg said that if the developer hadn’t pressured the council member and she changed her mind simply because she learned that many more residents supported the plan than she initially thought, then the penthouse could be considered a tip.

Unsubmitted jobs for the son of a politician

A state legislator in a powerful leadership position is trying to find an income for his adult son. He decides to ask several companies whose businesses could be drastically affected by the state legislation to pay his son. If they don’t comply, he says, they could lose government contracts or face crippling state regulations.

For this reason, several companies agree to pay the official’s son hundreds of thousands of dollars. When a supervisor at one of the companies that pays the legislator’s son asks him to do some work, the son threatens to “smash” his head.

This scenario is based on the corruption case against former New York State Senate Majority Leader Dean Skelos and his son, Adam. Both were found guilty of bribery, among other charges. A higher court overturned the convictions due to jury instructions, but both were convicted a second time.

Prosecutors said Dean Skelos abused his power to benefit his son.

“Once again, a New York jury heard a sordid story of bribery, extortion and abuse of power by a powerful public official in this state,” then-Assistant U.S. Attorney Robert Khuzami said in a statement after the second judgment. “And once again, a jury responded with a unanimous guilty verdict, in this case for Dean Skelos and his son Adam, sending a resounding message that political corruption will not be tolerated.”