Will Elway extend any of Broncos' contract-year veterans in-season?

Recently, I saw somebody ask a question of our own Chad Jensen about the likelihood of the Denver Broncos extending players with expiring contracts during the course of this season.
I knew what my response would be: "Highly unlikely."
That might sound like the Broncos aren't interested in extending anybody, but that's not the case. It's really a matter of caponomics. Let's review.
The Broncos, per Over the Cap, have about $4.8M in cap space for 2019. That number only accounts for the top-51 salaries — when the roster is finalized, the salaries for all 53 players on the active roster, any players on injured reserve and any players added to the practice squad will count. So the final number will either be slightly higher or lower, depending on who makes the final roster.
What does that mean for extending current Broncos? It means that it will only make sense to extend somebody if it allows the Broncos to gain cap space. Any extension that raises a player's cap hit doesn't help the cap situation.
Part of the reason why the Broncos are tight on cap space is because they accumulated a lot of dead money from players recently released or traded — they have $21M in dead money. Much of that goes back to the dead money from the two-year deal the Broncos gave Case Keenum last year, though some of it accounts for remaining signing bonuses for players such as Demaryius Thomas, Brandon Marshall and Darian Stewart.
The Broncos also gave a raise to Chris Harris, Jr., which took additional cap space. Consequently, the Broncos don't have much wiggle room at this point.
This doesn't mean the Broncos are in cap trouble for the long term. Next season, they are projected to have $48.7M in cap space, based on a projected salary cap of $200M. And that's before any cap carryover is applied and any cuts are made.
That still begs the question: "Why won't the Broncos extend anybody during this season?" Let's review a few players whose deals are expiring.
Shelby Harris: He's due nearly $3.1M in base salary from the restricted free agent he signed. Any extension would raise that cap number because you would give Harris a signing bonus that's large enough to let you spread out some of the fully guaranteed money during the course of several seasons. You also want it large enough to satisfy Harris and his agent in terms of a cash commitment.
Consider that Harris could be approaching Stephon Tuitt's contract in terms of the money he'll be seeking — and Harris could seek more than that, meaning an APY salary of $12M to $13M — and it's clear the Broncos can't extend Harris during the season.
Justin Simmons: Similar to Harris, Simmons carries a low cap hit ($2.2M) so any extension would raise his cap number. Simmons probably won't approach the deals that Landon Collins, Tyrann Mathieu and Earl Thomas received, but he could approach Lamarcus Joyner, who is earning $10.5M APY. Once again, it's not possible to extend Simmons at this time.
Chris Harris, Jr.: An extension could lower his cap number. However, he's likely to want to play for a contender in 2020 and, just as importantly, will want to be one of the highest-paid cornerbacks in the NFL. So he's not likely to negotiate with the Broncos for the time being. Things could change after the season, but until then, don't count on an extension.
Derek Wolfe: Though an extension could lower his cap number, and though Wolfe has indicated he'd like to finish his career with the Broncos, the team is likely taking a "wait and see" approach. Wolfe isn't getting any younger and his health has been an issue in the past. Therefore, the Broncos won't likely talk extension for a while.
For those who are worried that prices will go up unless the Broncos act now, prices have already gone up. The safety market was strong this offseason, so it's highly unlikely Simmons can be extended for less than $10M APY. Shelby Harris may not be an elite pass rusher, and he won't approach Aaron Donald's salary, but don't expect him to take the $9M APY range that Derek Wolfe took four years ago.
For those who want to ask about restructuring contracts to free up cap space, keep in mind that comes with a cost: Kicking the cap can down the road.
It's easy to look at, say, Joe Flacco's contract and convert his base salary into a signing bonus so you can extend Shelby Harris or Justin Simmons. However, you don't want to kick the cap can down the road with Flacco, because if he doesn't play well in 2019, you want to be able to cut him in 2020 with no dead money charge and a good chunk of cap space freed.
Kick the cap can down the road with Flacco and you could run into the same problem you did with Case Keenum: Moving on from a QB and stuck with a large amount of dead money on your hands.
Don't count on anybody taking pay cuts, either. The Broncos are at the point in which they aren't in a position to ask most veterans to convert money into incentives because they aren't a bona fide playoff contender at this point. Furthermore, John Elway is trying to shake the perception that he's too stingy in negotiations, so it's unlikely he'll ask anyone to take a pay cut.
None of this means that the Broncos will wait until the last minute to extend players they want to keep. Once the regular season ends, any extension a player signs starts with the 2020 NFL calendar year. That leaves the Broncos free to extend who they want, with a signing bonus that both allows the team to reasonably spread out the hit, while satisfying the player and agent regarding a long-term cash commitment.
Bottom line
Chances are the Broncos will, during the season, stay in touch with agents of the players they want to retain and get an idea about what an extension might look like. Then, after the regular season ends, they can get more serious about negotiations.
The Broncos will be in a tight cap situation this season, but once they ride that out, they'll be in great position to extend players. Broncos fans will just have to be patient and don't get caught up in the idea of kicking the cap can down the road.

Bob Morris has served as Denver Broncos On SI's resident cap analyst covering the Denver Broncos and NFL since 2017. His works have been featured on Scout.com, 247Sports.com, CBSSports.com, and BleacherReport.com.
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