#3 - Philadelphia Phillies
The Philadelphia Phillies won the NL East this year in dominant fashion but fell short in the postseason to their division rivals, the New York Mets. That's leaving just as bad a taste in the mouth of the Phillies as it did for the Brewers. That means they're going to be aggressive in their search for upgrades this offseason and they have the money to do it.
One spot where they could upgrade is their bullpen. Jeff Hoffman and Carlos Estevez are now free agents and there is no clear-cut closer for the Phillies on their roster right now. Jose Alvarado tallied the most saves of the current options with 13 last year, but he also had an ERA north of 4.00. Seranthony Dominguez was traded away mid-season for Austin Hays, who was just non-tendered by Philly.
The best player to get to help fortify their bullpen may, ironically enough, be the man who allowed the Mets to reach that NLDS against the Phillies to begin with in Devin Williams.
The Phillies have more than enough financial means to take on Williams for his final year of arbitration and they may even be the place that would sign him to a long-term contract if things go well, either before free agency or after Williams hits it.
Philadelphia is looking to "shake up" their team following their premature postseason exit and rumors are that third baseman Alec Bohm is on the market. The Brewers just so happen to need a power hitting corner infielder and a Bohm-for-Williams swap makes a lot of sense for both sides. The Brewers should be calling Philly about Bohm's availability and if those talks proceed, it's highly likely Williams' name is going to be brought up and it should intrigue Philly.
In order to make the value balance out, the Brewers are likely to have to throw in a prospect in that trade as Bohm has two years of control to just one for Williams. Still, that's the kind of win-win trade between two contenders that happens during the offseason.