The Hollywood Reporter did some more digging into the issue in a recent report.

Sony Pictures has held the licensing rights to the Marvel character since the 2002 Tobey Maguire movie from Sam Raimi and had some success with various follow-ups. After Disney acquired Marvel and started building its cinematic universe, they wanted to bring in one of the MCU's most popular superheroes.

THR outlines the simple 2014 agreement between Sony's then-chair Amy Pascal and Disney -- an agreement that was reportedly only four or five pages in length, which is rare for Hollywood:

Sony would loan Spider-Man out for one film, Captain America: Civil War, and in return, Sony would get [Marvel chief Kevin] Feige’s producing service for two movies. The deal was later revised to include both Avengers: Infinity War and Endgame. “You have to remember, Marvel wasn’t in the same place as it was now. There was a still a question of how far could this ‘superhero thing’ go,” says one insider familiar with the deal.

Everyone made a lot of money in this deal. An emboldened Sony decided to dive into the genre fully, making both Venom and the animated Spider-Man: Into the Spider-Verse, both extremely successful films at the box office. Only the latter proved a hit with both critics and on the awards circuit, having won the Best Animated Film Academy Award. 

According to THR's insider source, current Sony Pictures chief Tom Rothman "is thinking ‘Okay, we’ve learned everything we need to from Kevin’s playbook. We did Venom on our own and we did Spider-Verse.'"

Spider-Man HomecomingCredit: Marvel Studios

The latest film, Spider-Man: Far from Home, has grossed over a billion dollars and has become Sony's most successful movie ever, surpassing the haul of their previous highest-grosser: 2012's 007 movie, Skyfall.

According to sources, star Tom Holland is signed to one more movie, and Sony is also moving ahead with an Andy Serkis-helmed Venom sequel. THR theorizes that the studios will probably go back to the table and make another deal, because it's really to no one's benefit to exclude Spidey from the MCU.

Check out the No Film School podcast for more.

Source: The Hollywood Reporter