As the witness list of NFL powerbrokers continues to swell in the Colin Kaepernick grievance, one question will come into focus in the coming weeks: How unpleasant could attorney Mark Geragos make this process for the league’s fraternity of wealthy elites?

Geragos is skilled at disassembling witnesses in depositions and he will likely have the latitude to dig deep into the league’s closets during questioning, says a former judge who spent parts of two decades watching Kaepernick’s attorney in action.

“Most of your trial objections to relevancy and hearsay don’t come into play at all in a deposition. It’s just a free-for-all,” said retired Los Angeles Superior Court Judge Peter Lichtman, who is now one of the top arbitrators in California. “That’s how [depositions] function. In fact the standard is – so long as a question or subject is reasonably calculated to lead to admissible evidence – you can talk about anything. There’s just no real objections you can pose in a deposition other than if it’s an attorney-client privilege or work product privilege.”

That means Geragos is going to have the leeway to ask NFL team owners, coaches and team personnel a lot under oath. That will also go for commissioner Roger Goodell – when he is eventually added to the deposition list in the coming weeks. And some aspects of the NFL’s past disciplinary cases could find their way into the depositions, according to sources familiar with the Kaepernick grievance. Particularly in Goodell’s eventual questioning, which could deeply explore his role and actions as the league’s fundamental disciplinary hand.

The Ezekiel Elliott investigation? Tom Brady and deflate-gate? Goodell’s handling of Ray Rice? So long as the line of questioning is “reasonably calculated” to lead to admissible evidence reflecting on the treatment of Kaepernick, aspects of all of those situations could be on the table in depositions. It may even be likely, considering Geragos and Kaepernick’s legal team will try to build a picture of how the league office communicates with owners in times of crisis or negative publicity.

Whether Geragos can win head-to-head battles with a solidly sophisticated set of team owners and league executives remains to be seen. He has long been a well-known litigator in California, but his national reputation has risen considerably over the years through appearances in mainstream media and a history of high-profile clients. But Lichtman said anyone who judges Geragos through the media or celebrity prism alone is underestimating him.

“He’s one of the best cross-examiners,” Lichtman said. “He’s a phenomenal examiner. He phrases questions in a manner that no matter which way you answer, you’re kind of screwed. In terms of my experience, with him appearing in my courtroom, he’s a force to be reckoned with. Let’s put it that way. … He’s on my top-five list of attorneys that are the go-to attorneys – in anything, criminal or civil. The civil attorneys who underestimate him and say, ‘Well, he’s a criminal lawyer’ – that’s a severe mistake.”

After being admitted to the State Bar of California in 1983, Geragos began making his name as a criminal defense attorney. Some of his first high-profile defenses orbited in some fashion around the Clinton family, first successfully defending former President Bill Clinton’s business associate Susan McDougal (of Whitewater infamy), and then later defending Clinton’s brother Roger on drunken-driving charges. Other clients would include politicians, rappers, actors and actresses, along with the wealthy private elite.

Lichtman says that’s what makes Geragos such an intriguing opponent for the NFL. Geragos’ wealth of experience has blazed a trail through every conceivable economic, educational and social plateau. All of it giving him the experience to joust (and corner) just about anyone on the witness stand.

“When I was in complex litigation, we had very sophisticated people on both sides,” Lichtman said. “But that’s where Mark’s forte is. He’s very good at finding a particular strategy and presentation and going with it. It’s like playing 10-second chess with him. His moves are already made. He’s got a pre-planned strategy. He’s very adroit at thinking his points through and having a very nice aerial view of the situation. He breaks complex things into simplistic things.

“I always loved having him in my courtroom. Because I knew he was going to be very well prepared. The big thing that judges look for are guys that don’t fight over everything. He knows which hill to die on. He knows when to concede. That’s a good thing. Judges love him. He’s charismatic and articulate, too. He’s got everything going for him. That is a pretty good package.”

And now it’s a package the NFL will have to contend with moving forward. Depositions are expected to begin inside the next two months and potentially span for long, long after. The who’s who of the NFL is being asked to line up, with Geragos and Kaepernick’s team circling for the foreseeable future. If anything, it will be intriguing legal theater simply for the chance to dig deep into some NFL closets and find out what might be hidden inside them.

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