Rep. Alan Grayson will face the biggest fight of his political career as he runs for the Democratic nomination for Senate in Florida on Tuesday.

He’s earned the reputation of being so difficult in Congress that establishment Democrats like Senate Minority Leader Harry Reid of Nevada have actively said they want him to lose his race against Rep. Patrick Murphy. Recent polls give Murphy a solid lead in the primary. 

With a long list of inflammatory remarks, here is a look back at some of the most bombastic comments Grayson has made.

1. Die Quickly

Most people in Washington got to know Grayson as a freshman lawmaker during the 2009 health care debate. He took to the House floor with cue cards saying the Republican health plan was “Don’t get sick.” And if you do get sick, he said, the GOP plan was for Americans to “die quickly.” Grayson would later call the health care crisis “a Holocaust.”

2. ‘Taliban Dan’

In Grayson’s first re-election campaign in 2010, he compared his Republican opponent Daniel Webster to the Taliban, calling him “Taliban Dan.” The ad featured Webster saying, “Wives, submit yourselves to your own husband.”

The problem was, Grayson had doctored the footage from a Webster speech where he actually said: “Love your wife, even as Christ loved the church and gave himself for it, and as opposed to wives submit yourselves to your own husband.” Grayson would lose the race in 2010 before getting elected back to Congress in 2012.

3. “Gold Diggers Gotta Dig”

Grayson’s marital problems have served as a sore point during his tenure in Congress. Last year, after an agreement for an annulment with his ex-wife fell apart, Grayson blasted her:

“I’ll sum it up for you, gold diggers gotta dig,” he said.

4. “Sh–ting Robot”

Good talk w @AlanGrayson: “R u some kind of sh*ttng robot?! U go around sh*tting on people?!” he inquired, loudly

— Adam Smith (@adamsmithtimes) May 13, 2015

Grayson has been known to get cross with reporters.

Perhaps one of his most infamous outbursts came when he unloaded on Tampa Bay Times political editor Adam Smith, asking if he were a “sh–ting robot” and if Smith went “around sh–ting on people.”

When accusations of domestic abuse from his former wife surfaced this year, Grayson also threatened to have a a Politico reporter arrested. 

5. “Say my Name!”

Establishment Democrats’ hatred for Grayson is well-known but he also turned off many progressives when he challenged Reid.

When Reid visited the Congressional Progressive Caucus, Grayson asked if Reid knew who he was.

“Say my name,” Grayson said to the Nevada senator, asking why Reid had spoken about Grayson’s ethics issues.

“Because it’s true and I want you to lose,” Reid replied.

Before that encounter, Grayson had already made his contempt for the Democratic leader — who is retiring this year — known.

“Thank goodness that he will be gone from Washington, D.C., when I am sworn into the Senate,” Grayson said in February.