In April 2019, yoga instructor Naama Issachar was arrested as she tried to board a connecting flight in Moscow on her way home to Israel. Russian authorities said they searched Issachar’s luggage and found about 10 grams of marijuana.

What elsewhere in the world might have drawn a slap on the wrist in Russia resulted in drug-trafficking charges and a seven-and-a-half-year prison sentence. Russia then reportedly dangled Issachar as a bargaining chip, offering to make a prisoner swap or to free the 26-year-old Israeli-American in exchange for other political favors.

Issachar’s story is a cautionary tale for Brittney Griner, the American basketball star arrested at the same Moscow airport last month under strikingly similar circumstances. Griner is under investigation for large-scale transportation of drugs and facing up to 10 years in prison after Russian customs officials allegedly found vape cartridges containing hashish oil in her luggage.

While Issachar served nine months in prison before Israeli Prime Minister Benjamin Netanyahu intervened and negotiated her early release, experts in U.S.-Russian relations told Yahoo Sports that Griner shouldn’t count on such a deal. Her detainment comes during a time of renewed hostility and distrust between the former Cold War adversaries with Russia at war with Ukraine and the U.S. joining Western allies in imposing crippling economic sanctions.

"Whatever kind of bargain could normally be worked out at the political level is going to be much harder to work out right now,” said Tom Firestone, who spent 14 years as the resident legal adviser at the U.S. Embassy in Moscow. “We’re as close to cutting off diplomatic relations as you can be without actually cutting off diplomatic relations. That’s not a good environment to negotiate the release of a detainee."

Firestone’s comments come one day after Antony Blinken declined to speak specifically about Griner when asked how the U.S. could help her. Answering generally, the U.S. Secretary of State told reporters on Sunday, “Whenever an American is detained anywhere in the world, we of course stand ready to provide every possible assistance, and that includes in Russia."

The U.S. has so far been unable to negotiate the release of two ex-Marines that Blinken says Russia has “unjustly detained.” Trevor Reed was sentenced to nine years in a Russian prison in 2020 after he allegedly got into an altercation with Russian police. Paul Whelan was sentenced to 16 years in Russian prison in 2020 for alleged espionage.

It’s not just Firestone who questions how much help the State Department could provide Griner in the midst of a war. William Partlett, an associate professor at Melbourne Law School and an expert on Russian politics, noted there is far less of a U.S. consular presence in Russia than usual to assist with the case and that tensions between the two countries are only escalating.

“Given the decreasing connections and trust” between the U.S. and Russia, Partlett said, “any deal is likely to be more difficult and protracted.”

While Firestone says it’s important that Griner and her family stay in touch with the State Department in case a diplomatic solution arises, he argues that preparing a strong legal defense should be the top priority.

"That’s the primary field of battle here — Russian criminal law,” Firestone said.

The Russian judicial system is widely perceived to be subject to influence from the government, but Americans have successfully negotiated plea deals in the past. For example, Aubrey Lorber, 19 at the time, was released from prison in September 2019 after less than two months in custody when a St. Petersburg court found her guilty of "attempting to import marijuana purchased in the U.S. into Russia."

Drew Holiner, an attorney who advises in matters of Russian law, said that Griner’s best-case scenario is a similar plea deal or early parole for good behavior. “Absent some vindictiveness from Russia,” Holiner said that he wouldn’t expect Griner to serve even close to a full 10-year sentence.

For Griner, the best option appears to be her case remaining low-profile and non-politicized in Russia. Otherwise she runs the risk of going from a criminal defendant at the mercy of the Russian judicial system to an openly gay, American pawn who Russia President Vladimir Putin can make an example of for propaganda purposes.

So far Griner’s supporters appear to be conscious of the risks of speaking out against Putin and fanning the flames. Neither her agent nor the WNBA have commented since their statements Saturday acknowledging the situation and emphasizing their concern for Griner’s safety.

One of the only people close to Griner who has spoken publicly is her partner. In an Instagram post on Saturday night, Cherelle Griner said, “I understand that many of you have grown to love BG over the years and have concerns and want details. Please honor our privacy as we continue to work on getting my wife home safely.”

Two days later, Cherelle posted again and admitted trying to stay busy isn’t helping. "There are no words to express this pain," she said.

It’s unclear exactly how long Griner has been in custody because Russian authorities have not specified when in February she was detained. At the time of her arrest, Griner had just flown from New York to Russia, where the two-time Olympic gold medalist plays for European basketball powerhouse UMMC Ekaterinburg during the WNBA offseason.

Firestone said that Griner’s family did the right thing choosing not to publicize her arrest until Russia announced it and instead trying to work behind the scenes to get her free or to mount a legal defense. He said any criticism that Griner or her supporters lob at Putin or Russia can only work against her while she’s still in custody.

“If it becomes political, that’s not going to work to her advantage,” Firestone said. “It would be much harder for the prosecutors to reach some sort of plea agreement with her."