HARRISON, N.J. – It was a transfer day deadline that went down to the wire and was tricky, causing some serious stress for New York Red Bulls sporting director Ali Curtis. He might have even gulped down a couple energy drinks or two to stay alert and sort through pages upon pages of banal and Draconian MLS rules.

Wink, wink. He should try that Red Bull stuff.

Last week, the Red Bulls signed Israeli international Omer Damari, a move that was more complicated than at first glance. Damari is owned by Red Bull Leipzig, the sister club for New York, and was brought in on loan meaning that the move is temporary and not permanent.

But he is also one of three Designated Players now on the roster (big money slots often reserved for stars such as a David Beckham or a Thierry Henry), meaning that he’s an exemption over the maximum salary threshold. Which also means that Red Bull now has to pay $150,000 to the league to use their third Designated Player slot, per MLS’ arcane rules. Oh and by the way, the league determines who is a Designated Player based on salary, transfer fee and other factors.

Factor in that a league source says that Red Bull was trying to use Target Allocation Money (TAM), another wrinkle in the league rules, to apply to Damari and it really becomes head-spinning stuff.

“So traditionally, the way a player qualifies as a Designated Player is all based on compensation. And now that compensation is determined by MLS and the league office. Now, the club Omer is coming from, it is slightly a different process. And that, it is having a number of conversations with the league office in terms of what the valuation is on Omer and his compensation,” Curtis said during the press conference.

“And they take a lot of things into consideration with regard to past performance, compensation from his former club, a lot of those different data points. Then they make a determination on if the player is a Designated Player? Is the player a TAM player? Or is he just a senior roster player?”

Up to speed yet? Wait, it gets even more convoluted.

So to recap, Damari is owned by Red Bull Leipzig, of the same owner as the New York Red Bulls. They sent the forward on a temporary deal to New York but they still ultimately own his rights and want him back.

He is also a Designated Player, strangely enough on loan. And it is a loan deal that isn’t structured to see him stay in New York. Also, the league determined that he is a ‘DP.” Whew, caught up?

But wait, there’s more.

Typically, teams around the league will sign a player on loan and then make his option permanent. That’s not the case here. This loan deal has no such option to keep him in New York long-term.

As a part of MLS rules, each team is allowed two players on loan with no option to buy, meaning that it is a loan and only a loan and that the player will return back to the original club at the end of the deal. MLS doesn’t want to become a league where players go on loan from bigger teams around the world, essentially becoming a feeder league. So they want as many loan options as possible to become permanent. But they allow for two loans each year, per team, that are loans in the purest meaning of the word.

Before the deal to sign Damari there was no one in the Red Bulls roster who filled one of those two slots. Now Damari is considered as filling one of those two slots, with sporting director Ali Curtis telling Metro New York that the Israeli international is on a four-month loan with no option to make it a permanent move.

All part of a deal that was anything but normal.

“I think that every deal has its unique challenges and a lot of them take advantage of similar rules and guidelines. This one was unique and had its unique challenges. This one required a lot of communication between my office and the league office. I saw this deal as tricky but no more tricky than [Sacha] Kljestan deal or the [Gonzalo] Veron deal,” Curtis told Metro, citing two of his biggest signings over the past 20 months.

“This one came down to the wire. What I would say that provides an extra layer of stress because you add a deadline.

“We got it done the same day, the same day of the transfer deadline was also the same day we got the deal done. It’s the day when he was in my office, we got the paperwork completed and sent. The nuance, it’s the third DP. It’s a related club. The deadline of the transfer deadline, a lot of those are stressful but that’s my job. But I need to do those things well to give our coaches and our players an opportunity to succeed. We’re trying to build a real club that the fans can be proud of, the supporters can get behind.

“Because ultimately we want to win the right way but we want to win. But we have high hopes for this team, this year. We think we’re built to have an even more successful season than we did last year. We’re looking forward to it.”