Caitlyn Jenner Flips Her Position on Hillary Clinton, Faces Protests in Chicago on 'I Am Cait'

The former Olympian faces her harshest critics yet as she gets further on the road, visiting Chicago and the Democratic debates in Des Moines, Iowa.

Life on the road for Caitlyn Jenner has certainly had its
ups and downs.

On the new season of I Am Cait, the former Olympian's reality series documenting her
life as a transgender woman after publicly coming out in May 2015, Jenner and
her squad are embarking on a road trip across America. It’s an opportunity for
Jenner to meet with the LGBT community, while also figuring out what it means
for her to be the most visible transgender woman.

MORE: Candis Canye on Friendship With Caitlyn Jenner and Life After 'I Am Cait'

However, time spent on the bus has given Jenner’s squad -- Jennifer
Finney Boylan, Kate Bornstein, Candis Cayne, Zackary Drucker, Chandi Moore, and
newcomer Ella Giselle -- opportunity to press her about her feelings on dating
men (“I would have a hard time with that”), her conservative political views (“[Donald
Trump] would be very good for women’s issues”), and her harsh opinions on
Hillary Clinton (“She couldn't care less about women”).

While her coming out was largely celebrated by the media, Hollywood and the LGBT community, there have been a growing number of transgender people who feel her visibility is hurting support for issues faced by the community.  

In November 2015, Jenner was confronted by her detractors
after giving a speech at the 7th annual Speaker Series luncheon for the Chicago
House, which provides social services for those impacted by HIV/AIDS and other
LGBT issues, in Illinois. “You are an insult to trans people; you are an insult
to women,” a protestor could be heard in video exclusively obtained by
Entertainment Tonight

The moment was also captured by the I Am Cait cameras, showing Jenner -- confident and determined to
connect with her protestors -- approach one of the women shouting at her. “I
am not representing you. I’m representing myself,” she offered.

The crowd quickly reacted, upset the reality star reached out and touched the woman's arm. But neither Jenner nor her friends stayed long enough for the confrontation to get out of hand.  

“I thought she handled the situation with poise,” B96
Chicago radio personality Showbiz Shelly, who witnessed the confrontation, told
ET at the time. “By confronting the protesters in the way she did, she
emphasized the themes she talked about in her speech -- to be respectful, be
brave and stand up for what you believe in.”

“It was the first time for Caitlyn that she saw, in the flesh, their reservations about her,” Boylan explained, adding her personal reservations,
which she regularly shares on her own I Am
: “She’s a public figure for transgender people, but she’s a
problematic figure.”

MORE: Caitlyn Jenner Campaigns for 'Tangerine' and Transgender Actress Mya Taylor

Following the incident, Jenner’s road trip made its way to
Des Moines, Iowa, for the Democratic debates. Considering the tension that had
been building on the bus over Jenner’s political views, the team came to an
agreement to keep things civilized. 

And calm they remained until they met Clinton backstage at the debates. There, the women gathered together to meet the presidential hopeful, even snapping a group photo. Jenner, clearly starstruck by Clinton’s presence, reversed her position on the candidate. 

“I have to admit, I think she’s very good on transgender
rights,” she told Drucker. The night did not end before meeting Bill Clinton as

The change in position was certainly a welcome one by Jenner’s
squad, but their journey together is far from over. And with tensions still
high, the road trip is bound to hit more bumps.

However, as Giselle told ETonline ahead of the new season, it's about going beyond certain identities. "When you put a bunch of trans
people on a bus, the trans is taken away," she said. "All of a
sudden, it's just a bunch of beautiful humans."