Back in 2016, when Denver Broncos GM John Elway dined with San Francisco 49ers’ QB Colin Kaepernick, both were unaware of all the dramas yet to unfold. Coming off a Super Bowl win, Elway was in the market for a signal-caller to replace the irreplaceable Peyton Manning.

Elway was reacting to a trade request from the Niners’ QB and was ready to put together a deal that would give the former Nevada graduate a fresh start in the Mile High City.

Whilst Elway was ready to deal, he was far less willing to pay the remaining dollars on Kaepernick’s 49ers’ contract terms. In order to be given the opportunity to replace the legendary Manning, he would first have to show a large amount of salary cap-friendly commitment. To satisfy Elway’s terms and conditions, he would have to take a drop in his salary from $11.9 million to $7 million. These demands proved to be the roadblock that derailed the trade when Kaepernick felt his wallet couldn’t take the pinch, and the 49ers balked at bridging the $4.9 million gulf in salary numbers.

History eventually told the story of how this was the last big NFL chance Kaepernick would be offered. The quarterback’s high profile political activism and kneeling protests dooming his fate to be an NFL pariah. His grievance filed against the NFL of colluding to blackball him and stop him continuing his career has seemingly only strengthened the owners’ resolve against him. Faced with such powerful forces at the league level, his last chance apparently passing him by must only add to his pain and disassociation.

Despite the trade failing over monetary differences, it has brought heavy focus on whether or not Kaepernick is all-in on playing football anymore. How could he have ever foreseen the storm of publicity that transpired to totally freeze him out way back during his chats with Elway? At the time it was Elway himself who was risking even more by orchestrating a trade, as the move was far from being a slam dunk.

In simple playing terms, Kaepernick was starting to rapidly decline as an NFL level QB. His frequent benching’s in favor of Blaine Gabbert in San Francisco was a significant red flag of a player on a downward trajectory. Elway himself was a GM in need of a quick fix, with Manning retiring and Brock Osweiler taking a megabucks deal in Houston. Elway felt adding Kapernick’s arm and athleticism into the Broncos’ open QB battle was a risk worth taking if it could be done at a team-friendly salary number.

With inept QB play ultimately dooming the fortunes of the Broncos in the post-Peyton Manning era, it highlights how botched deals and negotiations have a ripple effect. It’s simply a great unknown if a basic change of scenery would have restored Kaepernick’s confidence and seen him flourish again in Denver. Elway’s tenure as the Broncos GM has always had its detractors on the basis that he hasn’t hit on quarterbacks, outwith the huge free agent swoop for Manning. In his attempts to replace the legendary #18, he has often stuck out when drafting similar big armed prospects.

The potential trade for Kaepernick back in 2016 was in so many ways classic John Elway, playing high stakes NFL poker similar to how he famously played the game. He has consistently made bold and risky moves that hold big upsides but also contain a high percentage of failure. Elway has also got a notorious ruthless streak, famously showcased by asking even Peyton Manning to accept a pay cut. So it’s hardly surprising that his own historical view of the trade saga was that there were no second chances in Denver, effectively that ship has sailed.

In the years that have passed since both Elway and Kaepernick met, their paths have dissected even further apart. Recent history of course found Elway trading for a proven Super Bowl-winning QB, who also ironically needed a fresh start, in former Baltimore Raven Joe Flacco. He also, once again, used the draft to select an Elway type guy in Missouri QB Drew Lock; the bombs-away type passer he so admires. True to his ultra-competitive nature The Duke keeps on swinging for the fences.

And as for Kaepernick, he still remains on the outside of the NFL looking in. Even with Roger Goodell now embracing the high profile and glitzy Jay-Z era, his career remains hamstrung by the causes that have transpired to create change. In the NFL as well as life, you never quite know when that one last big opportunity might have just brushed by you.