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I believe Castillo made it that long without getting signed due to owners being overly cautious during their first free agency cycle. I think a lot of them are getting the feel of how the finances work and didn't want to risk overextending themselves. And of course he was asking for a nearly $100M contract!
The uneven media revenue is indeed an issue; you can chalk that up to my inexperience when the league was started. Rather than blow the whole thing up and create a wild financial swing, we've decided to give the smaller market teams the opportunity to increase their market size gradually over time (along with a few other benefits).
Now it happens that the team making the signings in the two examples above is actually on the lower end of the market size spectrum (and good for them for not letting market size get them down!). Again, I totally have no problem with the team making shrewd offers and getting themselves a good deal; that's exactly what mid-market teams need to do to survive.
The only thing I'm questioning is the reality of a player asking for $90M over 5 years signing a multi-year contract mid-season for just $2M/year. If this were a lowball 1-year contract, I wouldn't bat an eyelash. The player held out for top dollar, the market dried up and he was stuck with taking what he could get or not collecting a paycheck for the whole year. Teach you to hold out, pal! It makes sense that the player would take what money he could on a 1-year deal, build his value up by playing well and then try again in next year's free agency market (hopefully with slightly more reasonable demands).
But a 3-year contract at a miniscule salary for what comperable players are making? I can't understand why the financial AI would allow that. I've heard that OOTP 9's financial AI is improved over OOTP 8; maybe it wouldn't happen on that platform? I would hope so, because a contract like this has the potential to impact the league for years. These are players in their prime signed for (relatively) dirt-cheap salaries. I know everything's fair in love and war, but I can see the potential for trouble over the long-term here.
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