First, big assumption that they are the same talent.
Also, irrelevant

Second, leftover cap space is irrelevant.

Is 189 greater than 185? Feel free to ask for help.

Would the owner be able to acquire said player if they had 185? No.

Are you a dumbass for allowing that owner to have a $4M cap advantage over you? Yes.

While we are at it, let's play Monopoly for money. You start with $1500, I'll start with $1700. Since it doesn't make a difference.

Just because you feel that a player with a $9m contract is "only worth" $5m does not necessarily make it true.

Somebody gave him a $9m contract.  Possibly to win a bidding war in which one or more other owners may have thought he was worth just under $9m.

Also, comparing players with similar ratings to see if they have similar contract value can be misleading.  Players often collect bigger contracts on the open market as free agents than if they are signed by their current team as either (a) an arb signing, or (b) an LT extension.  Open market vs. closed market.

booger makes a good point.    Team C may have made a bad signing.   Now, because he's willing to pay part of the current salary, he's being bailed out of his poor decision.  Why should he be helped?

Needs change. You could have signed a guy to a 4 year deal and needed him for the 1st 3 years. Come the 4th year, you have a prospect ready to come up and you don't need that player you signed anymore. Can you use him? Sure but if you can trade him you would like to. It doesn't mean he's being bailed out of anything. Or maybe when you signed him you were a serious contender and after several injuries and some guys under performing you realize you are going to go a different route. Not everything means you made a poor decision and you need to be bailed out. As I said, needs change and the ability to trade allows you to try and adapt to your new needs.

How long does it take a draft pick to become a BL player?    I'd say at least 3-4 seasons with very few exceptions.   So, when you're doling out a 4 year deal, you either have a player who'll take his place or you don't.   If you do, you're making a decision and now you have a redundant player.  Is that a good decision?   I wouldn't think so.

Cash in trades = bailing out the lazy or dumb or both.
Be off with it.

A snip from one of my comments in another thread:

"The problem is really not so much the owner getting the players/cash than it is the owner giving it up.  They tend not to get full value because A) winning takes them further away from a good pick B) they're only concerned with their position and not with the other contenders."

So, essentially, since the money is spent, the team giving up the cash will almost always throw in "another mil" to "sweeten the pot" because of the above.   Therefore, whatever "value" you see changes based on these factors.    As death said(and stole from me), cash is for the stupid, lazy or both.   Stupid and lazy shouldn't be rewarded.

Posted by boogerlips on 4/3/2011 1:39:00 PM (view original):
How is sending money with an overpaid player a bailout? If you're overpaying a player by 4mil, you've wasted 4mil. If you send that player to another team along with 4mil, you've wasted 4mil. The end result is the same financial situation that each team had before the trade. Which is the point. Cash is needed to make the exchange fair.
Bailing an owner out of a bad contract, would be accepting a trade without cash being sent.

"overpaying a player by 4mil".

Please explain how you can determine that a player is overpaid by $4m, as opposed to being overpaid by $2m or $1m, or even $1.

booger has tough time with the concept of "market value".   Ryan Howard's deal has no effect on the market because he was never a FA, right boogs?