Warning: Spoilers ahead for The Mandalorian season 2, episode 6, "The Tragedy."
The Mandalorian season 2, episode 6, "The Tragedy," revealed that Din Djarin (Pedro Pascal) has plans to break Migs Mayfeld out of prison in order to locate Moff Gideon (Giancarlo Esposito). Mayfeld was first introduced in season 1 as a mercenary who joined Din on a mission to rescue a prisoner on a New Republic correctional transport ship. The character, played by Bill Burr, ended up betraying the Mandalorian, but he never managed to escape the ship. Din got revenge on Mayfeld and the rest of the mercenaries, locking them in a cell. Despite being a prisoner, Din now needs his help for a new mission in saving Grogu from the Empire.
After their encounter with Ahsoka Tano (Rosario Dawson), the Mandalorian and Grogu traveled to the planet Tython so the young Force user could connect with a Jedi willing to train him. While at the ancient temple, Boba Fett (Temuera Morrison) arrived with Fennec Shand (Ming-Na Wen) in tow to get his Mandalorian armor back. Prior to making a deal, the group was ambushed by two shuttles full of stormtroopers. During the conflict, the Razor Crest was destroyed by Moff Gideon's ship, but more importantly, four Dark Troopers kidnapped Grogu. After acquiring the infant, the ship went into hyperspace, leaving Din with no immediate options.
Upon losing Grogu, Din hitched a ride from Boba Fett's ship and traveled back to Nevarro. The Mandalorian visited Cara Dune (Gina Carano), who agreed to become a Marshal for the New Republic, and requested information on Mayfeld. Din revealed that he planned to break the man out of his prison sentence, which turned out to be serving 50 years at the Karthon Chop Fields. Mayfeld received the sentence for his involvement in the season 1 mission, but specifically, for killing a New Republic soldier. While it initially seems like a perfect opportunity to bring back a random season 1 character, Mayfeld's past actually plays into Din's goal in locating Moff Gideon, and ultimately, rescuing Grogu.
The Mandalorian's Mayfeld Has Connections To The Empire
Mayfeld was already an expert mercenary by the time he and Din teamed up for the mission aboard the New Republic prison ship. Before that, however, the man was a sharpshooter in the Imperial Military. Not much was revealed about Mayfeld's life following the fall of the Empire, but it was presumed that he quickly became a mercenary to make ends meet. He also couldn't stay in one place too long considering he was a wanted criminal. While traveling the galaxy, Mayfeld surely encountered compelling figures whether they were reputable of fellow criminals. The fact that he already had connections to the Empire with his past as an Imperial sharpshooter, Din probably assumes that the man could track down Moff Gideon — either by using his existing knowledge and skills, or by reaching out to his contacts associated with the Empire.If Mayfeld doesn't have direct connections to Moff Gideon, he will most likely know others who do.
Mayfeld might not be very interested in working alongside Din given their history, but as a mercenary, Mayfeld is driven by rewards. Given that Mayfeld is currently serving a sentence, he desperately needs someone like Din to spring him; Din could offer freedom in exchange for his assistance in finding the Empire ship holding Grogu. At this point, The Mandalorian has proved that Din will go to any lengths to get the infant back considering the bond between them. Re-teaming with a former Imperial with a history of betrayal isn't ideal, but Din doesn't have many options.