The legendary Boston Red Sox pitcher's comments on "The Lead" seemed to come out of left field after Tapper had been asking Schilling about his controversial social media posts about transgender Americans and Muslims.
"I would like to ask you something as a person who is practicing the Jewish faith and has since you were young," began Schilling, a vocal Donald Trump supporter
who is mulling a 2018 Senate bid in Massachusetts.
"I don't understand -- and this is, maybe this is the amateur, non-politician in me -- I don't understand how people of Jewish faith can back the Democratic Party, which over the last 50 years has been so clearly anti-Israel, so clearly anti-Jewish Israel," Schilling continued. "I don't know what else would need to be done, said or happen for people to understand that they don't -- the Democratic Party is aligned for Israel only because we have agreements in place to make them have to be."
Tapper responded by telling Schilling he doesn't speak for Jews nor does he support either the Democratic or Republican parties, but guessed that perhaps "one of the reasons many Jews are Democrats has more to do with Democrats' support for social welfare programs and that sort of thing than it does for Israel."
"That's fair," Schilling replied.
"And I know a lot of Jews who are very strong supporters of Israel do support the Republican Party, but again, I don't speak for Jews," Tapper added.
"Right, no, I know you don't. I just always find it a great conversation for somebody of your faith to -- because I want to understand the reason behind some of those things, so I appreciate that," Schilling said.
Schilling also said he needed to talk with his family before making a formal announcement about a Senate run.
"When you look at, I think the state of media and the politics now, conservative families are fair game," Schilling said. "And I don't know that they want to be put through that and I don't know that I would want to put them through that."
Schilling also questioned why the media focused on the Republican presidential nominee's vulgar 2005 comments about women rather than devote as much time to discussing Democratic candidate Hillary Clinton.
"I'm curious as to why we spend seven or eight news cycles talking about disgustingly crass, inappropriate, sexist comments he made 10 years ago over the fact that every single day WikiLeaks is showing us that Hillary Clinton is exactly the criminal we thought she was," Schilling said.