While Freeman not being signed before the lockout isn't something to panic over, I do think it's a bad sign for those who wanted him to stay. If both sides wanted him here as badly as they kept saying publicly, they'd have settled on something reasonable before now.
From a purely comfort standpoint it would seem that Freddie would have wanted to have this mess settled and off his plate before the holidays, and with well over $100 million already banked it would make sense to give up a little bit of cash to make things easier for Alex to manage to keep the team competitive for the next several years. That's not to say trying to get his market value as a reward for what he's meant to the franchise is something fans should hold against him, it's simply an observation from afar - there are obviously other factors involved, and it would be perfectly reasonable for him to still be upset that they didn't offer him a Goldschmidt-type deal when they had the chance knowing he'd accept the minute it was on the table.
From an organizational standpoint, this break in signings gives Alex not only the time to quietly plant the stories needed to make it look like Freddie was being greedy and holding a gun to their head while talking to the Yankees/Red Sox/Blue Jays/Dodgers to help with fan sentiment, it also gives him the time to put a potential Olson deal together that can be agreed to the minute the transaction ban is lifted - he can't talk to free-agents during the lockout, but there's nothing preventing GMs from working out deals to be announced at that point. This timeout makes it more likely that he's able to remove that much more emotion from the equation without the time crunch of his other options coming off the board. As many here have previously explained, it's not that hard to see that spreading that money between multiple other players gives potentially gives you a better chance to extend the team's competitive window through the end of the Acuna/Albies control. I realize many of those people aren't in favor of extensions for some of these guys, but if you traded for Olson and signed him to a 5 year/$125 million deal starting now ($113 million new dollars) and could sign Fried to the 5 year/$85 million deal McCullers got from the Astros ($78 million new dollars) you'd have spent roughly the same amount of money you'd have given Freeman but you'd control Acuna, Albies, Olson, Langeliers or Contreras, Pache or Waters, Harris, Shewmake or Grissom, Fried, Davidson or Muller, Strider/Tarnok/Elder/Woods/Vodnik/Estes/Cusick/Schwellenbach through 2026 and Riley and Anderson through 2025. If The Battery continues to be successful - and payroll continues to increase (as we've been led to believe it will) - there's no reason to expect this window will close before Ronald and Ozzie's deals expire. The core would be in place and you'd only need to supplement it with guys on short-term deals. It would be just as hard for anyone to fault AA for doing that as it would be for them to be upset with Freddie for asking for what he's worth.
A terrible position to be in coming off winning it all, but the fact that they haven't been able to settle this by now definitely makes it seem more likely Freeman finishes his career somewhere else IMO.