Winner: Cara Dune
Cara Dune of Alderaan has had an eventful story arc since her introduction back in Chapter 4 of The Mandalorian. She began as an ex- shock trooper of the Rebel Alliance, then ended up staying on Nevarro as Grefe Karga’s right hand. This season, she continued her career advancement from being the sheriff of Navarro to receiving the promotion as a marshal of the New Republic.
Her newfound responsibilities did not negate her loyalties though as she came to the Mando’s aid in rescuing the Jedi-foundling, Grogu. Her military skills were also on full-display this season as she battled her way through stormtroopers both on Nevarro and on Moff Gideon’s cruiser. She even showed a merciful side when she granted Mayfeld his freedom after he aided Team Mando on their mission to retrieve information on Grogu’s whereabouts. I think this makes her a winner.
The ex-Imperial sniper-turned-mercenary was first introduced to audiences back in Chapter 6 of The Mandalorian. Despite beginning as allies, Mando and Mayfeld clashed with one another and the latter was left incarcerated by the New Republic.
Mayfeld was then recruited by the Mando for his mission to obtain information on Grogu’s whereabouts, following the Jedi-foundlings kidnapping by the Dark Troopers on Tython. Mayfeld proved not only that he was a trustworthy ally, but he also earned another special honor — becoming the first living being to see Din Djarin’s face after the Mandalorian had sworn an oath to remain unseen.
Mayfeld also gained a bit of retribution for some deceased squad-members against a former commanding officer of the Empire, after killing him inside the Imperial base that they had infiltrated. Mayfeld even showed off his sniping skills while Team Mando was escaping the facility, therefore dismissing any doubts about his marksmanship.
Mayfeld’s path of redemption was ultimately rewarded with his freedom after Cara Dune allowed him to escape custody and begin a new lease on his life. These events showed that Mayfeld was a winner.