Part of the 2021 'Super Draft' that included the likes of Nick Daicos, Sam Darcy and Nasiah Wanganeen-Milera, Chesser was struck down by injuries during his four years with the Eagles.
An ankle injury ruined his debut season, before playing 32 games during the 2023 and 2024 campaigns.
After undergoing ankle surgery before the 2025 season, Chesser returned with four promising appearances to end the year.
The Eagles offered the wingman a new two-year deal to remain in Perth, but the 22-year-old elected to return to Victoria, where he studied at Melbourne Grammar.
"I was finally starting to get some continuity in my body and confidence in my game, and I just needed a fresh start," Chesser told AAP.
"Coming to a great club back in Melbourne with my family and friends around me, and just a fresh environment, has been an awesome change for me.
"(Just a point to prove) to myself, and to the club for showing faith in me getting the trade done and getting me here."
Admitting the constant injury setbacks at West Coast were tough, Chesser insists his experience could have been far worse.
"I had a lot of great support around me over in Perth, even though I was so far away from home," he said.
"I had my girlfriend (Sylvie) over there.
"I had a lot of mates inside the club, they were a great support.
"Some that were injured at the same time - Oscar Allen, Tom Cole, Dom Sheed, who were great support to me, and I learned a lot from them and I'll forever be grateful for that."
Carlton, who finished 11th after a disappointing start to the season, won't try to change Chesser's role.
"The wing role suits my strengths quite well," he said.
"Running and carrying the ball, bring some speed in transition on the wing, so that's probably where I'll look to play, and hopefully I get an opportunity."
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