Squid Baron is greedy, rude and dishonest, though is ultimately not a malicious figure and only fights to protect his family and property. Despite that, he still does not hesitate in using his children as weapons during his fight against Shantae.
In Pirate's Curse, Squid Baron fills a humorous role. He has become self-aware of his role as a video game character and consequently, his role as a "filler boss" in the series with no actual relation to the plot. This leads to him suffering "post-boss syndrome", suffering depression over his defeat on wish to not be a filler boss again. He thus wishes to find a new purpose in life, with most of his interactions with Shantae being repaying her for helping him find a new purpose in life. After repeated frustrations, he finally embraces his destiny as a filler boss. He doesn't seem disturbed by this, as he seems happy even when Shantae beats him again.
For some odd reason, Shantae seems to gain the same awareness whenever she talks to him, making Squid Baron a sort of fourth-wall nullifier.
The Squid Baron first appears in the game at the entrance of his labyrinth, waiting for a tasty meal. Once Shantae gets there with the meal she got from the Chef Girl, he lets her in and showcases a rather friendly attitude, until the moment she mentions being here to get his Magic Seal. He attempts to reason with Shantae, but she doesn’t budge. He then flees and once cornered in his room, becomes overtly hostile, not wanting Shantae to take the Seal. The player, as Shantae, then proceeds to defeat him in a Boss Battle.
In his boss battle the Squid Baron has the ability to teleport himself just like regular squids can. He will try to land on Shantae her head by doing this. He can also charge for Shantae one time but if he eats a tasty meal he will charge 7 times and then stop. As mentioned in his Personality, he can also summon his children to the battle and they won't do anything beside walking but can hurt Shantae if she touches them. His children can reward hearts so Shantae can heal herself. When the Squid Baron is damaged 120 times, he is defeated and he explodes in what Shantae later describes as a 'Stage Clear Sequence' and Shantae is rewarded with the first Magic Seal.
The Squid Baron reappears near the end of the game at the lighthouse, shortly after Sky and Bolo revealed to Shantae that Mimic has disappeared. He comes to ask Shantae's help to retrieve three of his babies, the Golden Warp Squid Babies. Shantae is distrusful at first, based on their last encounter (cynically breaking the fourth wall when she mentions she saw him disappear in a boss battle explosion) but warms up to him when he reveals that Mimic was abducted by the Zombie Trio of Rottytops, Abner Cadaver and Poe and that one of the Golden Babies owns an artifact which could help her in her journey. After Shantae has retrieved the Babies, the Squid Baron reveals that the artifact is the Mermaid Bubble which allows Shantae to attack underwater. In the ending scene, he is seen alongside the heroes at the lighthouse, with his babies running around the screen, but does not have any line.
Early in the game, Shantae meets up with the Squid Baron outside of Sequin Land Palace. Feeling depressed due to "post-boss syndrome", he asks that Shantae give him a suggestion on where to go for a change of scenery. After Shantae gives him a Travel Brochure (found in the sewers beneath the palace), the Squid Baron gives her some Squid Oil and leaves for the sunny beaches and sexy co-eds.
The two meet again on Tan Line Island. Upset at finding that the island was not at all like the brochure's description (as the tourist season had long ended), the Squid Baron falls into another bout of depression. Shantae again tries to cheer him up and is given X-Ray Specs for the effort. At the very end of the Lost Catacombs, the Squid Baron appears to announce that he is going to embrace his destiny as a "filler boss" and fights Shantae as the dungeon's last enemy, Squid Baron 2.0. As a new ability, he summons armor to protect himself, which can only be shattered with Shantae's scimitar attack. After being defeated, the Squid Baron is happy to have found his calling and anticipates his future appearances as a boss. As a reward for giving his life meaning, he gives Shantae the Mud Bog Island Map.
Squid Baron reappears as the fifth boss. He is summoned by the Hypno Baron; Shantae believes this is part of a plot to destroy the world, though it turns out that this was merely because Hypno Baron wanted to purchase a license to use Squid Baron's likeness on a line of T-shirts. After Squid Baron is reduced to half health, both Barons team up to defeat Shantae, though they are in the end defeated themselves.
Squid Baron shows up later in Scuttle Town's art gallery no worse for wear. He tears a Velvet Poster down from the gallery, hoping to use the space for a Squid Baron poster, ignoring the fact he doesn't have one; this sends Shantae on an optional fetch quest. Should Shantae find a Squid Poster, Squid Baron will reward the player with Risky's Buckle.
To be added