According to Peter King, before shoveling a mountain of cash to Osweiler the only time either had ever had with him was a 10-second hello back in 2014 during training camp when the Texans held a joint practice with the Denver Broncos. Said King:
Until Osweiler signed with the Texans on March 9, that 10-second niblet of time was the extent of the personal interaction between the quarterback and the three men most important to his success in Houston. The owner, Bob McNair, agreed to guarantee $37 million to Osweiler without ever meeting him. The head coach, O’Brien, never got to speak to Osweiler during the free-agency period, to look him in the eye and find out if he was the man O’Brien wanted to build his offense around. The hands-on offensive coordinator, George Godsey, never got to drill Osweiler on his strengths, weaknesses and how he might fit into the Houston scheme. But it’s not as if the Texans brass were being reckless with such a critical decision. It’s that league rules forbid any direct contact between a player and a prospective team before the official opening of free agency.
That's a huge risk for the Texans. It was a risk that John Elway was unwilling to make, despite countless hours of meetings and watching Brock practice.
And it's a risk that is mandated by NFL rules. Even if the Texans wanted to speak with Osweiler, they couldn't. Which just seems crazy considering the amount of money involved.
It was clear O'Brien doesn't like the current setup where teams cannot officially speak with potential free agents during the legal tampering period, noting, "There really should be a period where, say a week before free agency, a guy can make some trips. Without that, you have to find a way to research guys, but without seeing him and talking to him face-to-face, there’s always going to be something missing."
However, I suppose that's the risk you take to make the big splashes on Day 1 of the free agency period. In a way, despite the Broncos current anxiety over the quarterback situation, they dodged a bullet by letting Osweiler walk. In hindsight, not having an heir apparent to Peyton Manning gives Elway some time to find a much better long term solution at the position.
Be it this year, or in the coming years. Elway won't feel the pressure to give an heir apparent a few seasons to fail if failure is to be the final outcome.