One of the most powerful Orthodox rabbis in America was arrested Tuesday for allegedly spying on nude women in his synagogue, but possibly sinful behavior by Barry Freundel may be more damaging.

Documents obtained by The Jewish Channel several months ago and reviewed The Daily Beast reveal that Freundel was booked on a cross-country trip with a woman who was not his wife this year, which is prohibited under Orthodox laws of yichud. It’s not clear when they met or what the exact nature of their relationship was.

Freundel’s work responsibilities until last year included setting standards for Orthodox conversion in the United States and overseeing thirteen rabbinical courts around the country, Until last year, Freundel served as the chairman of the Conversion Committee for the Rabbinical Council of America, the largest body of Orthodox rabbis in the United States. In his position, he oversaw 13 rabbinical courts and set standards for Orthodox conversion. In both positions, Freundel has been in a position to decide what activities make one eligible and ineligible to be an Orthodox Jew. Freundel is also rabbi of the prominent Kesher Israel synagogue in Washington. Not only is the congregation full of prominent Jews like Treasury Secretary Jacob Lew but it’s also one of America’s most modern, letting women read from the Torah and hold positions of leadership.

Freundel also sets standards for kosher food service in the D.C. metropolitan area as vice president of his region’s Vaad, which supervises and certifies kosher establishments.

In 2013, Freundel had announced a seven-week “study leave” beginning May 22, during which he would “conduct research” and “complete a book” on matters of Jewish law, according to his synagogue newsletter. “This study leave is an important aspect of the life of a pulpit rabbi, providing opportunities for study and professional growth which might not otherwise be possible,” he said in the newsletter.

At 11:05 a.m. on May 22, Freundel was booked to be in a private room on a train bound for Chicago with a woman who was not his wife. According to the train’s literature, the room comes with “two reclining seats [that] convert to a bed,” a sink, toilet, and a “sweeping picture window.”

They apparently boarded a return train in Chicago bound for D.C. at 6:10 p.m. on May 28. This 18-hour trip was in a less nice room, but one that had two seats that convert into a bed. After breakfast the next morning, they disembarked. One person who requested anonymity said Freundel emerged from the train without a kippah (skullcap) on his head, which he’d normally be wearing at all times as an Orthodox rabbi. Freundel was with his female train companion, too.

A phone message for Freundel at his synagogue was not returned, nor was an e-mail to his personal account. Calls to his cellphone and home numbers were not answered.

RCA president Rabbi Leonard Matanky said Tuesday of Freundel’s trip, “we never had any proof of such a thing.” Matanky said the RCA has not made any decisions about Freundel’s status or considered what it might mean for converts, because “it’s an unfolding story” with his arrested and that no decision-making process would begin until more details are available. Matanky did say, however, that “if, God forbid, any rabbi, any person were to violate the law, no one is above the law.”

Freundel’s arrest comes at a moment of great tension regarding the question of who is considered a Jew. The Israeli Chief Rabbinate in recent years has invalidated many thousands of conversions, arguing that the rabbis converting these individuals were too lax in enforcing strict Orthodox standards for applicants, like ensuring they’d keep kosher after the conversion process was over.

This has meant that people who thought they were Jewish were suddenly left without the ability to get married or send their kids to Jewish schools in Israel. In 2006, Freundel was the RCA’s representative to negotiations with the Israeli Chief Rabbinate to ensure that those converted by RCA rabbinical courts would not be similarly treated. Revelations of Freundel’s activities could thus throw into chaos the status of thousands who've converted under standards set, overseen and enforced by the rabbi, not to mention the many hundreds who've converted directly under Freundel.