Angel Pagan is making $11.25m, so giving an OF $10m+ to replace him will be no issue. It's what organizations that value winning championships do.
So if their window is closing in 2019, then that's nowhere close to the end of their window.
And the Giants won't trade Bumgardner, they'll fill in with good pieces around him, just as they have done these past 7 years.
How do you fill in around Bumgarner when the farm system is dried up? They filled in around guys before because they had a good farm system.
What do you do when Cueto exercises his opt-out in 2 years? Or, more concerning, what do you do when Cueto decides to opt-in to the end of the deal because he's struggled so badly?
How do you guarantee that your replacement for Pagan will be worth 2.0 WAR? You're going to pay a guy like he's worth 2 wins, but he's also going to be in his 30's because that's just the nature of the beast with free agents, so where is that guarantee coming from? Do you just re-sign a 35 year old Pagan?
You're acting like these things are so neat and tidy, but ignoring the big picture.
Teams have limits on what they'll spend. This idea that teams will spend whatever is necessary in order to win is just childish. I don't know if it's the dumb little media narrative surrounding Steinbrenner or what, but the object of all of these owners first and foremost is to make money. Nobody is repeatedly taking a loss in the name of winning, any owner who says he's taking a loss or is breaking even so that he can win is a total liar.
They might be in a net loss position once you take the non-cash expenses into account, but their operating cash flows are absolutely going to be positive.
If I didn't make it clear, my guess is they either rebuild as soon as Cueto opts out after 2017 (meaning the window is closed in 2018) or they give it one more shot with Bumgarner in 2018 but then ultimately trade him when he still has a lot of value prior to 2019 (meaning the window closes for 2019).
For all intents and purposes, though, they're operating as if 2016 and 2017 are their last clearly defined years of contention.