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Derek Wolfe has to be waking up this morning feeling bad

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during Super Bowl 50 at Levi’s Stadium on February 7, 2016 in Santa Clara, California.

Ezra Shaw

When they’re preparing to negotiate a contract, players often have to balance short-term security against the potential for a bigger payoff if they’re willing to incur some risk.

So as Broncos defensive end Malik Jackson prepares to bathe in the reported six-year, $90 million deal with $42 million guaranteed with the Jaguars, one of the guys he left behind has to wonder why.

In January, the Broncos gave defensive end Derek Wolfe a four-year extension worth $36.75 million, with $17.5 million guaranteed.

That’s a pretty big difference, in case you’re not as good at math as I am.

Part of it comes from security, as Wolfe reportedly wanted a deal done before the playoffs started. But Jackson also took advantage of a bump in the salary cap, and a handful of teams with the need to spend big. With the Jaguars one of the teams needing to get to the CBA-mandated 89-percent cash spend floor, they were going to do a big deal with someone.

But, for lack of a better phrase, the Broncos took advantage of a guy who wanted to stay put.

“Last night I called my agents and the deal was already on the table and I said, ‘Look, let’s just take this deal,’” Wolfe said of the contract, at the time he signed, via the Denver Post. “‘I don’t want to leave. I love this city, I love the them, I love the organization, the coaches, my teammates and everything, so I couldn’t be happier. I’m in a place that I love to be, so why would I leave?”

And while there’s no reason to shed a tear for Wolfe — he’s still rich, lives in a beautiful city, and is a key part of the best defense in football — it’s hard not to wonder if he’s looking at today’s headlines and thinking “what might have been,” because what he might have been is much, much richer if he’d waited a few months.