The only way to extend Boras guys like Wood and Crews is to give a ridiculously player friendly extension with player opt outs that put all the risk on the team for maybe an extra year or two of team control. Guys like that, you just realize you have them for their 6 or whatever years of team control. Enjoy that those last 3 years should be their peak years. If the team isn't looking like they'll contend the last year, then trade them. There's no good reason to think of a Boras guy any differently than that (cheap owners or not).
If a guy is ditching Boras looking for an extension, then we better do it though.
I agree here. Unless a player simply wants to spend their career somewhere, a possible superstar isn't signing a long term contract extension that is team friendly. The Braves are a weird exception.
If James Wood has a really good year, I think he Nationals should try to extend him. I just won't hold my breath.
Luis Garcia level guys are where I prefer early extensions. He had a great season, seemingly has a new approach, let's sign him up before he gets to free agency. A bit of a bet on our part, but not a dangerous one like handing a multi hundred million dollar deal to ap layer with less than a year of MLB service.