When it's all said and done, Blake Bortles' extension during the 2018 offseason might very well go down as the worst contract extension in NFL history. Or the best, if you're Bortles. The Jags are reportedly planning on moving on from Bortles this offseason, and the ramifications of doing so will be pretty stark on their salary cap.

According to Ian Rapoport of NFL Network, Thursday night ultimately cemented Bortles' fate. With Cody Kessler struggling to produce points on the field, there was no thought to bringing Bortles in off the bench. He's done in Jacksonville. 

"Blake Bortles' future does not include the Jacksonville Jaguars. They are expected to move on from him this offseason," Rapoport said. "Unlikely to trade him because of the huge contract extension they signed him to last offseason. So there's going to be a dead money hit -- I believe $16 million -- they'll have to split over two years. But we likely have seen the last of Blake Bortles in January."

As in, come January, the Jaguars will cut Bortles. Or at least at some point before the new league year when Jacksonville is required to get underneath the salary cap. They are expected to be more than $23 million above the cap number when the season ends, which is going to create a serious squeeze for the Jaguars front office.

Had they not given Bortles the extension, the Jaguars could simply let him walk into free agency and use the vacated cap space to pay other players or get their budget balanced. Instead, Jacksonville is going to face a mammoth cap hit in 2019: if he's on the roster, Bortles has a cap hit of $21 million next year and if he's not on the roster, he'll take up $16.5 million in dead cap space. It's not even that much in terms of savings, that's how terrible the deal is and how bad a spot the Jaguars find themselves in. 

Jacksonville can designate Bortles a post-June 1 cut, which would give them more cap savings this year. In that situation, Bortles would take up $11.5 million in dead cap space in 2019 and $10 million in 2020. That might be a preferable option, but the Jaguars wouldn't be able to access the additional $5 million until after June 1, so ripping the Band-Aid in March might be preferable. 

Worth noting here: Bortles has, according to Mike Florio of Pro Football Talk, offset language in his contract. If he signs with another NFL team, the Jaguars could see some cap relief as a result. They're going to be tagged for a minimum $6.5 million in dead cap space, but the actual number could fall between that and $16.5 million depending on what Bortles gets from another team. 

One potential scenario exists for Jacksonville to get out from under the Bortles money: they could pull off an Osweilerian deal to ship him out. 

Brock Osweiler, famously signed by the Houston Texans to a contract that was worse based solely on the terms of the deal (Bortles had much less leverage than Osweiler, who was actually a free agent) and eventually shipped out to the Browns <em>with</em> a second-round pick in order for the Texans to avoid eating Osweiler's dead cap hit. Cleveland would eventually cut Osweiler, who signed back with the Broncos last year before signing with the Dolphins this season. It pays very well to be tall and capable of throwing a football at fast speeds with questionable accuracy. 

Spotrac pegs eight different teams who will have north of $60 million in salary cap space heading into the 2019 offseason. The Jets and Colts are both expected to have north of $100 million, which make them viable candidates to eat the $21 million cap hit for holding Bortles (or the $16.5 million in dead money). It doesn't feel like a deal Chris Ballard would do, but the Jets make a lot of sense. They gave up tons of picks to move up -- in a deal with the Colts -- and acquire Sam Darnold last draft. They could use a second-round pick, and if the Jaguars were willing to give one up in order to move on from Bortles without the hit, the Jets should be willing to consider it.

They have Darnold and Josh McCown on the roster right now. McCown is more equipped than Bortles to lead and relieve Darnold, but the downgrade to Bortles, if a second-round pick was added, would be well worth it. 

Whatever the case, Bortles puts the Jaguars in a rough financial position, one that was entirely unnecessary because they simply could have kept him under contract in 2018 and moved on if it didn't work out. 

All of this adds up to the idea that the Jaguars' Super Bowl window is closing. Jacksonville has big-time decisions coming with Malik Jackson, Calais Campbell and Marcell Dareus. There's no chance all three can stay, and one might be the max based on their cap situation. Jalen Ramsey, Myles Jack and Yannick Ngakoue are all eligible for extensions this offseason. They all have good reasons for demanding said extensions and refusing to show up until they get paid. 

That's before we even get into the future of Doug Marrone and Dave Caldwell -- a future that could end up with Tom Coughlin on the sidelines again. It's not out of the question, or even far-fetched.