Will Cain is an ESPN Radio host who, according to Will Cain, likes to look at issues differently from everyone else. He can certainly add to that list the issue of NFL teams asking prospects ridiculous, offensive and discriminatory questions.

Last week Cain took to the airwaves to wax poetic about the value of asking college athletes if they are gay, if their mothers are prostitutes, or what kind of fruit (the apples and bananas variety) they like to be. NFL teams get something out of these questions, Cain argued, and claims of inappropriateness should be set aside for the good of coaching staffs who never ever ever ever ever effectively use the information they gather from prospects to draft correctly.

“NFL prospects answer questions, often stupid, inane, inappropriate, maybe even discriminatory questions,” Cain said. “These questions are without a doubt inappropriate. But that’s the point. they’re inappropriate and meant to be inappropriate. … There’s value in the reactions and answers they get.”

ESPN sent Outsports this statement on Cain’s hot take:

“Will is not saying the questions are appropriate or good but he believes inappropriate questions are asked by NFL teams for the reactions they get from prospects.”

To be clear, I don’t think Cain is some homophobe with a microphone. Conversations this weekend with people who know him emphasized that he’s not. Cain apparently likes to look at issues from a different perspective.

Yet I’m convinced he just likes to look at issues from his own perspective.

To better understand Cain’s position, you have to listen to his every word. It’s not easily summed up in a headline — There’s nuance to his positions. Though my headline nails it: Cain attacks everyone who says these questions shouldn’t be asked.

Cain doubled down on his show, claiming that anyone advocating for fairness isn’t living in reality.

“‘Fair’ and ‘what I want’ don’t guide me through every single interaction in my life,” he said. “‘Fair’ is not real. ‘Fair’ is not something to walk around life demanding, much less expecting.”

As a former card-carrying Republican (and I do emphasize former), I understand this mentality better than many in the LGBTQ community. There’s an overriding idea that people are the masters of their own fate and the captains of their own soul. I still love the concept, yet there’s a grey area that is important to embrace.

Cain’s biggest mistake here — exemplified perfectly by the above quote — was pointed out by a caller who tried to explain that the white Republican ESPN host was looking at life wearing blinders and failing to put himself in the shoes of others.

“What do my politics or my race have to do with any of it?” Cain asked.

In this case, a lot.

Cain’s rant demonstrated an inability or unwillingness to see the drastic and life-threatening imposition asking a gay athlete about his sexual orientation forces a closeted gay athlete into. Ryan O’Callaghan, the former NFL player who was drafted by the New England Patriots even as he was plotting to eventually kill himself, said a question like that would have “scared the shit” out of him.

This isn’t a hypothetical. This is real. There are, as a matter of fact, gay athletes being considered for the NFL Draft.

How could O’Callaghan or other gay athletes be expected to “pass” that test?

O’Callaghan told Outsports last week that he knows of closeted gay athletes eligible for this year’s NFL Draft, meaning one of them — if he were at the Combine — may be forced to come out on the spot or lie.

This isn’t a hypothetical. This is real. There are, as a matter of fact, gay athletes being considered for the NFL Draft.

How is a gay athlete supposed to answer that question? He’s scared to death of what will happen if he answers the question honestly. And if he lies, he’ll come across as a liar — Cain himself said these questions are filmed and vetted. So he either has to be a really good liar, or he’s out.

To Cain, that seems to be the athlete’s fault as the NFL prospect is in charge of his own actions and emotions.

Of course Cain doesn’t seem able to see this dynamic, or he doesn’t want to see it. It’s an inconvenient truth.

Eventually — I assume after he started reading Twitter and realized just how “privileged” he sounded — Cain circled back during his show and suddenly claimed that NFL teams should not ask if a prospect liked men.

This was, of course, after espousing the benefits of such a question.

A producer finally chimed in and pointed out that he was making no sense.

“Which side are you on?” The producer asked. “You just said you can ask that question and now you’re saying you can’t.”

Cain essentially claimed he was a victim and no one understood him. He then pointed out that teams can’t legally ask the question while continuing to entirely miss the ethical point of the issue.

“It opens the door for discrimination,” Cain explained before he again defended the question. “But that’s a balancing act. It’s a balance against the information you could get. Asking someone if they like men reveals all kinds of information beyond whether or not they actually do [like men].”

If there is an Olympic medal to be handed out for verbal gymnastics, Cain just won gold.

He then offered a ridiculous rationalization that was pure rationalization.

“You could find out if somebody’s homophobic from asking that question,” he continued. “And if you don’t want to draft somebody who’s homophobic you may have just found that out.”

So Cain was suddenly arguing that NFL coaches sit in a room and place a priority on drafting players who aren’t homophobic.

If there is an Olympic medal to be handed out for verbal gymnastics, Cain just won gold.

Asking NFL prospects if they are gay — regardless of the motive — is illegal, it is immoral, it violates league policy, it violates the collective bargaining agreement with the NFLPA, it puts gay athletes in an unfair and terrible position, and the NFL front office has mandated that the practice stop.

I wouldn’t begin to claim Cain is homophobic. That’s not the takeaway here. From what I’ve been told this weekend, he’s a “good guy.”

I think I’m a good guy too. But sometimes good guys do stupid things. Sometimes I say stupid things. Sometimes I’m wrong.

Cain said something stupid. And he’s wrong.