BOSTON (CBS) — No one has been more critical of the NFL during this whole DeflateGate mess than The Washington Post’s Sally Jenkins.

Jenkins, who has received a few marriage proposals from Patriots fans thanks to her coverage of the case, joined 98.5 The Sports Hub’s Toucher & Rich on Tuesday to discuss the case. Many have said not to focus on Judge Richard Berman grilling the NFL in the two settlement hearings that were held in federal court in New York, because he could just as easily turn around and rule in favor of the league. But Jenkins believes his line of questioning towards the league is good news for the Brady camp.

“You hear that from lawyers that you can’t read too much into the judge’s questions and remarks during this phase, but the other thing to consider is if you’re trying to push for a settlement, you would think he would be doing the same thing other side. It’s the one sided-ness of it that the judge is signaling to the NFL that if you don’t move, I’m going to torch you; be prepared for a very unfavorable decision from me,” said Jenkins. “You wonder why he would encourage the Tom Brady side not to settle, because that’s what he seems to be doing with his remarks and questions, giving hope to the Brady camp.”

Jenkins also pointed out a few potential fatal flaws in the NFL’s case. Brady may have a better chance to win because the league did not allow the NFLPA to question Jeffrey Pash, a high-ranking attorney for the NFL who edited the Wells Report before it came out.

“It looks like a potentially fatal mistake,” said Jenkins. “You look back at the record of this whole affair, and early on, the NFL described Pash as ‘the co-leader of the investigation’ or ‘the co-council.’ The NFL has moved the goal line in several instances and that was one of them,” she said. “Either Jeff Pash was involved in this investigation or he wasn’t. Either his notes are germane to the case, or they weren’t. If they were, and they appeared to have been because he edited the Wells Report, then the NFL denied Tom Brady and the counsel the opportunity to see his notes and question Pash.”

There are other aspects of the NFL’s case that could lead to Roger Goodell’s decision to be overturned.

“The cell phone, ironically, is what Goodell used to hammer Brady with in the four-game suspension, but they never gave Brady and his counsel fair notice that the cell phone was required. In fact, Ted Wells said very specifically, ‘we don’t need the phone, just give us the records.’ To turn around and slap Tom Brady with this draconian punishment for getting rid of his cell phone or destroying it or whatever he did, that’s fine if you told Brady on the front end he better keep the phone and give it to us. That’s something worthy of severe punishment. But if you tell him and his lawyers you don’t need the phone, you can’t turn around and give him a penalty for losing or destroying or getting rid of the phone.”

Many wonder why the NFL hasn’t settled out of court. But Jenkins believes the league is expecting Judge Berman to rule against them, and they like their chances of winning later on in appeals court.

“I think they’re aiming for the appeals court, but that’s just my feeling just watching the league over the years.”

Listen to the full interview: