Tampa Bay Rays
Needs: Pre-arbitration talent
Assets: Pitching, position player depth
The Rays are always stocked with talent and always turning over their roster. Once players start to get into arbitration and get out of their price range, they're moved out for cheaper assets and there's always someone just as good or better ready to take their spot. The Rays are in that spot now with their corner infielders, among others.
Rumors have it that Harold Ramirez and Isaac Paredes could be available in a trade and either one would help fill a corner infield need for the Brewers. They'd be ideal pickups for the Crew. Randy Arozarena is reportedly potentially available, but it's unlikely the Brewers swing for an outfielder, even one as good as Arozarena.
Tampa always has pitching. Tyler Glasnow is the big name that's expected to be traded this winter. He's due $25MM in 2024, which is quite pricey for Milwaukee but it's one year of Glasnow and then he hits free agency. There are a lot of teams in trade talks for him and the Brewers may be priced out of his trade market.
There's also relievers that Tampa could move. Shawn Armstrong and Andrew Kittredge are in their final years of arbitration and could be trade candidates of interest to Milwaukee.
The Rays are always searching for pre-arbitration talent and the Brewers have plenty of that. If they end up moving away someone like Arozarena or (more likely) Manuel Margot, that could open up a spot for one of the Brewers young outfielders in a different trade if they so choose.
These two teams have connected numerous times on trades in recent years and it stands to reason they could connect again as both teams have needs and assets that line up.