As long as Mark Attanasio has owned the Milwaukee Brewers (and going back further than that to be honest), the team has had to limit their spending. While that hasn't prevented the Brewers from making the playoffs in six of the last seven seasons, it has greatly limited their overall ceiling as a club and been a huge reason why they have been "forced" to let high-end talent leave in trades and free agency once they started commanding real money.
While this isn't a unique problem in the game of baseball as a number of smaller market teams have operated with strict financial parameters, it does make things harder and decrease the margin of error with the moves that are made. When former Brewers general manager David Stearns left town, there was real concern that the Brewers would begin to fall off given those constraints and how good Stearns was at his job.
Some of those concerns ended up being overblown. Matt Arnold has performed ably since Stearns stepped down and ultimately ended up getting hired by the Mets and Milwaukee has won the division the last two seasons which isn't nothing. However, this offseason is feeling more and more like it could be a step back while Stearns is very obviously living his best life in New York without being handcuffed when it comes to spending.
David Stearns' giddiness about this offseason feels especially bad ahead of tough Brewers offseason
To be clear, this isn't a situation where Stearns threw Milwaukee under the bus or was openly critical of his time with the Brewers. When he visited Milwaukee in late September, Stearns praised the team and talked about how nice it was to see the people he used to work with every day. Stearns wouldn't have left the Brewers if he wasn't at least a little frustrated about the lack of spending, but any executive who cares about winning longs for having more resources at their disposal.
Still, it is hard to ignore Stearns talking about having the "entirety of the player universe" as options available to him with a HUGE grin on his face when responding to a question about the difference in running the Mets versus the Brewers. To be fair, if any of us got handed Steve Cohen's debit card and had Juan Soto on our offseason shopping list, we would be shouting from the rooftops about how good life was.
As for Milwaukee, the organization is coming off a heartbreaking playoff loss to Stearn's Mets and faces declining TV revenues thanks Diamond Sports' implosion, the likely loss of Willy Adames in free agency, and probably trading closer Devin Williams to capitalize on his value before he inevitably joins the growing group of former Brewers making more money elsewhere.
All of that ends up being a lot of headwinds for Arnold and the Brewers to navigate this offseason. While it is entirely possible that Milwaukee will end up on the other side in a good spot, it is no wonder why Stearns can't hide his joy in not having to deal with these sorts of obstacles anymore.