Orlando City pursuing São Paulo star Ganso makes a crazy kind of sense

There's been a strange battle being fought between MLS side Orlando City and Brazilian giants São Paulo of late. The Brazilian giants owe the American side a fair bit of money after breaking their side of a loan agreement involving Kaka, who Orlando had loaned to São Paulo last season while they waited to officially join MLS.

The agreement involved multiple friendlies between the two sides, with Orlando City keeping most of the ticket money, as well as the Brazilian side paying some $1.3 million of Kaka's wages. None of that happened, though, and now Orlando are threatening to take São Paulo to court over it -- unless they give up Paulo Henrique Ganso, the team's star midfielder who's long sought a move outside of Brazil.

São Paulo have until Thursday to accept Orlando City's proposal (SP give Ganso but get US$ 1.89m) reg. the US$ 4.3m São Paulo owe them.

— Paulo Freitas (@Cynegeticus) July 21, 2015

São Paulo are in a major financial crisis right now, looking like they'll have to sell off significant portions of their squad in order to stay afloat. Many players reportedly are owed a hefty chunk of change in unpaid wages and bonuses, and things are threatening to come apart at the seams. Using a player to help solve some of those financial troubles in this way is a little unusual, but in this case, it could work out well for all parties involved -- if they can get over some potential pitfalls, that is.

Why it makes sense

São Paulo have some pretty serious financial woes right now, and this move would allow them to kill two birds with one stone -- clearing their debt to Orlando City and getting Ganso's wages off the books, and they'd even get a little bit of cash to work with as well. As they try to work their way out of their cash-strapped quagmire, that deal has got to look pretty tempting for them to pull the trigger on.

For Orlando City, it's easy to see the attraction, as well. Ganso would be arguably the most talented creative midfielder in MLS, and at 25 years old, he'd still have plenty of peak playing time for them to enjoy if they can hold onto him for a few years. He'd have to be a Designated Player, but the new Targeted Allocation Money rule would allow them to buy down one of their two non-Kaka DP's and clear a slot for him. This would be the exact kind of statement, high-upside move Orlando's ownership has seemed to be fond of making.

Ganso also formed a terrific playing partnership with Kaka when the two were at São Paulo, playing some of his best football while alongside the Brazil legend. If Orlando can get that same form rolling again with the pair in their side, they could be awfully hard to stop in MLS.

Why it doesn’t make sense

For all the sense this would make for São Paulo to do in light of their financial woes, they seem fairly uninterested in actually doing anything about their debt to Orlando City. The MLS side has set a Thursday deadline to get their problems settled before filing a lawsuit, but there's been little to no reaction from the Brazilians thus far. That doesn't seem promising.

The legal aspects of this are also potentially tricky to clear up. Orlando City are basically saying "if you give us Ganso, we'll forgive your debt," which sounds simple but might not be that easy when it comes to getting contracts finalized and approved. If this does happen, don't be surprised if it takes a long time to get done as the two clubs' legal teams -- and Ganso's, for that matter -- finagle it into some kind of shape that makes everyone happy.

There's also two problems on Ganso's side of the deal -- he's long wanted a move to a bigger league in Europe in order to raise his profile, and he may not be convinced that joining a new MLS side is the way to do that, even if he would get to play with his good buddy Kaka again. There's also the issue of third-party ownership, which has killed several potential deals that would have seen Ganso cross the Atlantic over the last few years. Such arrangements are supposed to end soon, but there's been no indication that Ganso's rights have been freed up yet, which would be a huge stumbling block to get through in any negotiations.

Likelihood it happens

This move would be complicated and tricky and strange to pull off, and not just for one or two reasons. It makes a lot of sense for both parties, but there's so many hurdles to clear it's hard to see it getting done. With that in mind, it's hard to give this more than a 2/10 chance of happening.

This is a post from our transfer rumors section. For news, analysis and more, check out the main SB Nation Soccer page.