The 2022 MLS offseason calendar

With MLS Cup 2022 in the books (and, uh, wow what a place in the books it will occupy!) the real starting bell of the offseason has officially been rung. The next two months will feature numerous offseason roster events, where MLS teams will be able to utilize the many weird and wonderful mechanisms to adjust their rosters before the 2023 season.

With their roster in need of improvement, you can be sure that the Portland Timbers will be active and involved in at least some of the below key events. Before they all kick off, here’s the dates you need to know for the upcoming offseason:

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November 7-9: Trade Window open

All of the hubbub might actually kick off on the day this is published, with the two-day trade window now officially open. This window has historically been pretty active in a year with an Expansion Draft, like this one. So expect some MLS teams to be wheeling and dealing this week.

How this impacts the Timbers: Brace yourselves — this might be where the Timbers lose Eryk Williamson.

There have been rumblings since pretty minute the final whistle sounded on Portland’s season that the talented midfielder was angling for a move away from Portland. Not-so-subtle instagram posts and Twitter likes expressing his dissatisfaction at not playing a role in the Timbers’ final game of the year stoked the fires of Williamson wanting a move, and apparently there is indeed some smoke to that fire. And recent reports of Portland being close to acquiring Brazilian attacking midfielder Evander also casts doubt into Williamson’s future with the Timbers.

If the relationship between the Timbers and Williamson is irreparable, the Timbers would want to maximize their return on him. A significant portion of any sell-on fee to a club overseas would be split between Portland and DC United as part of the deal agreed to when Portland acquired Williamson’s rights, so if a move happens the Timbers would likely look within the league. So brace yourselves for a move to potentially be announced in the next 48 hours.

And hey, would you look at that, we have our first Williamson trade rumor (kind of):

And of course, the Timbers may also leverage this window to bring in and move players regardless of what happens with Williamson.

November 11: Expansion Draft

Another year, another new MLS team, and another MLS Expansion Draft. This time, St. Louis City SC will be selecting up to five players from other MLS teams to help build out their inaugural roster. MLS teams will release their list of 12 players they choose to protect from the draft on November 10.

How this impacts the Timbers: Expansion drafts have affected the Timbers in the past. Whether it is to the draft directly or to deals made around the draft, they have previously lost players like Donovan Ricketts and Zarek Valentin to MLS expansion. Portland has a lot of MLS experience on their roster, and so there is a good likelihood that one of their players may be targeted on Friday.

November 14: Bona Fide offer & club option deadline

This is the deadline for teams to make offers (in the same manner as an 20th century oil baron, apparently) to players that are out of contract in order to retain their MLS rights. Also, teams must exercise or decline club options on players who have those in their deals for 2023 by this day.

How this impacts the Timbers: The Timbers already announced their roster moves and options last month, so not a ton will impact Portland here. The only player the Timbers are still in negotiations with is Nathan Fogaca, so this would be the deadline for them to extend an offer to him if they want to retain his rights.

November 16: Free agency begins

MLS clubs may begin negotiating with free agents on this day, and there are going to be some prominent players in the mix. The biggest name is forward Josef Martinez, who is set to leave Atlanta United this offseason. Presuming nobody picks up his gigantic salary in the re-entry process, he will be set to his the market.

How this impacts the Timbers: The Timbers have been pretty averse to free agent acquisitions since it began in 2015. Despite his lack of production on the field, you could argue the most significant on they ever made was acquiring Ned Grabavoy in 2016, as he is now leading the Timbers soccer operations. Other than that, free agency just hasn’t been a mechanism that Portland has looked to for key players.

Will that change this year? Will they make a run at Martinez? I’m doubtful, but who knows!

November 17: Re-Entry process, Stage 1 & End of Year Waivers

It ain’t MLS without more weird drafts. The re-entry process is the method by which players who are out of contract, but not yet eligible for free agency, can be allocated to new team. Teams who select players in the first stage must extend a Bona Fide offer or extend any options on the players’ contract, and due to that not many players get selected in this first stage.

Teams can select those players that are not eligible for either free agency or the re-entry draft in the waiver process on this day as well.

How this impacts the Timbers: The above confusing enough for you? The Timbers haven’t usually acquired players at this stage, but hey, could always change! I wouldn’t count on it though.

November 22: Re-Entry process, Stage 2

This is the re-entry draft for any player that wasn’t selected in stage 1 and doesn’t opt out. Teams are free to re-negotiate new deals and aren’t required to extend offers, so this stage is a little more active.

How this impacts the Timbers: See blurb for re-entry process stage one, although due to the increased flexibility the odds that Portland does something here are slightly higher (though still pretty low).

December 21: 2023 MLS Superdraft

Three rounds of college players being selected by MLS teams, in reverse order of how the final standings finished.

How this impacts the Timbers: The Timbers are set to have their highest draft pick in a good long while, so keep an eye out on some of the draft big boards. The Timbers haven’t exactly been a hallmark of drafting and developing, but they have found some slight success in recent years. Highlights of Portland’s previous drafts are of course Darlington Nagbe and Jeremy Ebobisse, and recently they’ve found some talent in the likes of Zac McGraw and Justin Rasmussen. They could be active in this year’s edition, so it might be worth tuning in.

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A reminder of Portland’s current roster status as the silly season heats up:

Portland Timbers 2023 Roster *as of Oct. 17

Goalkeepers: David Bingham, Aljaz Ivacic, Hunter Sulte

Defenders: Pablo Bonilla, Claudio Bravo, Larrys Mabiala, Zac McGraw, Juan David Mosquera, Justin Rasmussen, Bill Tuiloma, Dario Zuparic

Midfielders: David Ayala, Sebastián Blanco, Diego Chara, Yimmi Chara, Marvin Loría, Santiago Moreno, Cristhian Paredes, Eryk Williamson

Forwards: Dairon Asprilla, Diego Gutierrez, Tega Ikoba, Felipe Mora, Jaroslaw Niezgoda