It’s almost time for the most relevant season for the Philadelphia Union: The offseason calendar where hope springs eternal, everything looks good on paper and rumors can sound infinitely better than the underlying reality.

It’s time for the annual deck reshuffling of MLS’ single-entity system into brand new teams via the league’s many player-acquisition mechanisms. With MLS Cup in the rearview mirror, December is rife with drafts, windows and other miscellaneous opportunities for teams like the Union to seek the pieces they hope will prevent them from having to wait so long from the end of their season to the opening of the marketplace.

Here’s a rundown of what the next could look like (plus a reminder of the mechanisms springing to life this week):

Monday, Dec. 8: From 9 a.m.-1 p.m., the trade window is open. That’s where deals negotiated over the last month and already in place will be finalized and ratified, potentially including the rumored deal the Union have in place for the Amobi Okugo to head to Orlando City.

Sources have confirmed to me the Union have completed deal sending Amobi Okugo to Orlando City for 100K in allocation money. #DOOP #OCSC
— Ives Galarcep (@SoccerByIves) December 8, 2014

Other deals that have been reported are Tally Hall to Orlando City, Nat Borchers to Portland and Michael Harrington to Colorado, while there will certainly be others. After 1 p.m., the trade window closes until the end of the Expansion Draft.

Wednesday, Dec. 10: Here’s the busy day. The Expansion draft for Orlando City and NYCFC will be held. By that time, we’ll have a list of the players the Union will have protected for the draft. Once the draft concludes, the trade window reopens, allowing expansion clubs to peddle their new players. Also Wednesday is the Waiver Draft, which usually is pretty uneventful. This year, it’s another chance to snap up former Chivas talent that went undrafted in the Dispersal Draft.


Thursday, Dec. 11: Trade window closes at 5 p.m. and won’t reopen until after the first stage of the re-entry draft.

Friday, Dec. 12: Phase One of the Re-Entry Draft, which involves players whose options were not picked up. In Phase One, teams must sign players at their existing contract level or automatically trigger the built-in option in their contracts that their former club passed on. The Union will pick seventh. It is presumably by this time that the Union will publicly release their contract decisions in terms of options picked up or declined, something that hasn’t been forthcoming. (By my reckoning, only the Union, Portland and the MLS Cup finalists New England and Los Angeles haven’t released their lists yet.) You’ll recall that the Union used Phase One of the Re-Entry Draft to acquire Corben Bone last season. After Phase One, the trade window re-opens and remains open until Dec. 17.

Thursday, Dec. 18: Phase Two of the Re-Entry Draft. This is the more active of the two phases (22 players were picked over the last two years, compared with just six in Phase One) since teams have more flexibility in negotiating new deals with players. The Union, who acquired Conor Casey by this mechanism two years ago, made no additions last season.

So, that’s drafts Wednesday and Friday, while trades are possible Monday, Wednesday, Thursday and Friday. Expect flurries of action Monday morning, then probably Wednesday as Orlando City and NYCFC get dealing. Most of early next week will likely involve players re-negotiating deals with clubs to avoid the Re-Entry Draft’s second stage.