I've long felt that the organization will trade him when the time comes, but in recent days, seeing his interviews and how the team has hyped him up as their "ace," I can't help but wonder if the team is going to try and extend him (I'm not sure I would support this decision). I am fully aware that that is not how this team has operated, to date, but his case may fit differently than the pitchers traded in recent years.
He seems to be an eyes-wide-open, driven professional that is taking nothing for granted. He already signed one extension with the team that raised him as a pro. I think he knows that he'll need to keep performing at a high level to get the next contract. In his interviews it seems like he is big on family, and perhaps by extension, loyalty. He has become a de facto leader. His English is strong enough to really take the lead in interviews and connecting with both teammates and fans. He seems like a "safe" extension in the sense that he's a pro, he'll work his tail off, and he'll be an excellent organizational ambassador.
Contract-wise, he's a tier below the tippy-top starters. If he were a free agent today, as a 28-year-old, I think he would get 5 or 6 years. At the end of his current contract (presuming a team picks up the 2026 option), he'll be 31, and I think at that point, he'll only get 3 or 4 years. I think the following contracts would be comparable...
2024 - Eduardo Rodriguez (30 years old) - 4 years - $80M - AAV $20M
2025 - Sean Manaea (32 years old) - 3 years - $75M - AAV $25M
2025 - Sonny Gray (34 years old) - 3 years - $75M - AAV $25M
2025 - Luis Severino (30 years old) - 3 years - $67M - AAV $22M
2022 - Jose Barrios (27 years old) - 7 years - $131M - AAV $19M
There's a number of other deals that are comps, including Pablo Lopez, Yusei Kikuchi, Marcus Stroman, etc.
Putting all of that together, and assuming that Freddy is WILLING to extend (a big "if"), I can see an extension that includes the Brewers turning down his $8M option in the following ranges...
5 years (2026-2030) for $75M - AAV $15M
or
7 years (2026-2032) for $90 - AVV $13M