So I’ve been having this ongoing conversation with a friend about upgrading my smartphone, which has this annoying tendency to call my friends and family without telling me. (My mobile phone thinks I’m lonely, apparently.) I’d like to get myself a shiny new Android phone of some sort, but I’m a Verizon customer, and my New Every Two upgrade doesn’t kick in until next July, so I would have to pay full price now for an upgrade. Said friend is encouraging me to switch from Verizon to Sprint, which has a few phones that interest me, but this would also be more expensive, because I would have to pay Verizon a termination fee. Plus, I’m not convinced that Sprint’s network coverage is superior to Verizon’s.

So the question boils down to this: do I pay full price to get a better phone and put a stop to random butt-dials now, or do I deal with this for 9 months and end up with an even better phone in July for much less? Is upgrading now really worth X number of dollars to me?

It’s one of those strange cognitive dilemmas that Dan Gilbert — the psychology professor at Harvard, not the comic sans-loving Cleveland Cavaliers owner — wrote about in his book Stumbling On Happiness, in which he suggests that human beings almost always get these decisions wrong. We overestimate the joy something will bring us and fear unhappiness will last longer than it actually does. We make comparisons that have little to do with the actual value of a transaction. When given the option between $50 today and $60 in a month, we reach for the $50 that we can get now, because we don’t recognize the value in waiting for that extra $10.

Which brings us to Wayne Rooney, who just had a dramatic falling out with manager Sir Alex Ferguson and has decided he wants to leave Manchester United. Despite Rooney’s poor form as of late, most clubs would jump at the opportunity to lure him away from Old Trafford — especially the few “rich” clubs like Real Madrid, Barcelona and nouveau riche Manchester City who can afford him.

Here’s what complicates matters for both Rooney’s current club and the clubs that would pursue him: the Webster Ruling.

For those who don’t recall, FIFA ruled two years ago in the case of Andy Webster that any player, after a set period of years,  can buy out the remainder of their contract for the remaining value of that contract. For players under the age of 28, that period is 3 years. The Webster Ruling is the reason Man United sold Cristiano Ronaldo to Real Madrid for £80 million in 2009. If Ferguson held on to Ronaldo for one more season, the club would have gotten only £12 million in return for him.

Now Man United faces the same dilemma with Rooney, who could buy out his contract with the club in the summer for a piddling £5 million — far less than Rooney could fetch on the open transfer market.

Since Ferguson is the unquestioned boss at Old Trafford, he has little choice but to move Rooney on now to whatever club will shell out the big bucks for him. But what club will spend £45 million in January on Rooney now when everyone knows you could spend £40 million less by waiting until July? Is that 4-5 months really worth £40 million? Maybe a club thinks it can sell £40 million worth of jerseys in that stretch of time; Real Madrid reportedly had Ronaldo’s transfer fee covered after one year of merchandise sales. Still, couldn’t a club sell just as many jerseys in 6 months time and end up with more money in the long run?

What will likely happen here is a trade. Real Madrid has an unhappy striker on their books in Karim Benzema, who was pursued heavily by Man United in 2009. Reports are already surfacing that Real will offer Benzema and cash to Man United in exchange for Rooney. It’s the perfect deal for both clubs, as it gives Man United far more value for Rooney than they can get in the summer, and it allows Real to get rid of a “problem player” and reunite Rooney and Ronaldo, who have already won that Champions League trophy Real covets so much, without appearing to spend an obscene amount of money.

Of course, Real could easily play hardball with Man United by reminding them how much less they could pay for Rooney in July. On the other hand, that €28.5 million that Real spent on Benzema is also a depreciating asset of sorts, and the powers that be at the Bernabeu might believe the club and its fans would see more value in trading Benzema for Rooney sooner rather than later.

I’d love to hear what Dan Gilbert might have to say about all this. He’d be the strangest guest Football Weekly ever had.

(It’s worth noting, by the way, that Everton would be thrilled to see this deal happen. As Match Fit USA points out, Rooney’s contract has a 25% sell-on clause in it, which could bring millions into Goodison Park — millions that could bring Landon Donovan to Everton on a permanent basis, perhaps.)