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Your guide to the dates & deadlines of the MLS offseason calendar

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Major dates to know ahead of the upcoming offseason, and what they mean for PTFC.

Bennett Dewan

As it is with anything in Major League Soccer, they really don’t make it easy on themselves. With two different types of league-allotted allocation money, ever-changing and never transparent salary numbers, and draconian rules of player acquisition (some team out there has got to already have the “Discovery Rights” for Messi), the league has seemingly more opaque rules and regulations than a government agency.

And it’s is no different for the MLS offseason. With MLS Cup 2020 firmly in the rearview mirror (shouts to Caleb Porter), we can all turn our eyes squarely to the silly season. There are a number of key dates for the opening of transfer windows, trade windows, and drafts (so many drafts) coming up rather quickly. Rather than trying to sift through all of the rules and impacts of them on your own, I thought I would take a stab at trying to lay out the timeline and significance of each move here, specifically pointing out how each phase of the offseason could impact the Portland Timbers. Here we go.

(I’m going off of the calendar MLS provided here. If you want to review the current list of players eligible for the various league drafts, you can do so here. Bear in mind that that list will be updated as some pending free agents may re-negotiate with their current clubs.).


December 13: Half-Day Trade Window

For four hours on Sunday, the league was open for business. This was the first opportunity this offseason that teams had to trade assets — players, international roster spots, and allocation money. Why am I starting with a date that has already passed? To point out how it impacted the Timbers and the moves they made.

How it impacted Portland: The Timbers used the opening bell of the offseason to build up their war chest. The reported trades for Julio Cascante and Marco Farfan were made official, both for differing amounts of General Allocation Money (GAM). The Timbers also traded a 2021 international roster spot to NYCFC in exchange for additional allocation money. At the end of the day, the moves Portland made amassed them $710K in GAM (potentially more with the reported performance-based incentives in Cascante’s deal). What can Portland put that money towards? It can be used to assist in player acquisitions, or be used as a tradeable asset itself. My guess is that a decent chunk of that money is planned to be used towards a permanent deal for the acquisition of Felipe Mora (if it happens), with any residual for in-league player acquisitions.

Craig Mitchelldyer, Portland Timbers

December 15: Expansion Draft

With Austin FC entering the league next season, it will soon be time again for that time honored tradition of letting them pick players off of other team’s rosters. Current teams can choose up to 12 players on their rosters to protect, and Austin FC will have 5 rounds to choose any player unprotected. Here’s the list of eligible players.

How this could impact Portland: It most likely won’t at all! Due to the fact that there was an expansion draft last season, any team that had players selected are exempt for this season’s edition. Due to the Nashville selecting Zarek Valentin last year (miss you Z!), the Timbers cannot have any players selected this year. There is always the chance that Portland could strike a deal with Austin to have them select a player that the Timbers then trade for — as Houston did with Nashville for Valentin last year — but Portland fans can rest easy knowing that no one from the roster will be plucked this week.

December 16: End-of-Year Waiver Process

The first of the processes by which players who are not currently rostered might find a home. The criteria for which player qualifies and is available in which drift is about as clear as mud, so it might take a bit to parse through. If I’m reading the requirements correctly, the players who qualify for the waiver draft are those whose a) options were not picked up or are out of contract, b) do not have their rights of refusal held by an MLS team and c) do not meet the requirements for the re-entry process or free agency. If you’re thinking “Wow that doesn’t seem like it would be a lot of players, this seems like a silly draft” …you’re right!

How this could impact Portland: The waiver draft has been notoriously quiet over the years, with usually a maximum of one or two players being picked. This is due to the small pool of players and inflexibility with contract options, and I anticipate the 2020 edition will be no different. You never know what a team will do, but the odds are pretty low that we see the Timbers do anything here.

December 16: Free Agency Opens

This is the beginning of the good stuff. December 16 marks the day that clubs can start negotiating with players who are out of contract and qualify for the league’s Free Agency requirements. According to the league website, “Free Agency eligible players are out-of-contract and option-declined players who are at least 24 years old and who have completed a minimum of five service years.” Both the years of service and age requirements have been lowered for the first time since 2015, so the pool of potential free agents will be a lot larger this year.

How it could impact Portland: Portland’s history of free agents has been...underwhelming. Portland’s first free agent signing was Ned Grabavoy in 2016, who subsequently retired at the end of that season, took a role in the Timbers front office, and is now the Timbers’ Technical Director. The team’s only other free agent signing was Chance Myers in 2017, and he played a grand total of only 44 minutes that year before being waived the next year. With a bigger pool to choose from and an uncertain international transfer market, this could be the year we see Portland look internally and make their first free agent signing in three years.

December 17: Re-Entry Process, Stage 1; December 22: Re-Entry Process, Stage 2

The next two stages are where the bulk of player movement has historically happened, outside of intra-league trades. The re-entry draft has seen some significant player movement in the past, with 2019 being especially active. According to the league website, the players eligible for this draft are those that are “at least 22 years old and have a minimum of one year of MLS service who are out of contract and did not receive a Bona Fide Offer or whose contract options were not exercised by their clubs.” Essentially, any player that isn’t eligible for free agency and is out of contract may be available. Players selected in stage one must either have their options picked up or be extended a “Bona Fide” offer. Those selected in stage two are free to have their contracts re-negotiated. Teams select in reverse order of finish at the end of the 2020 regular season, with Austin getting the first pick.

How it could impact Portland: Portland has utilized the re-entry draft to add some significant pieces in the past. They drafted Jermaine Taylor ahead of the 2016 season, and before that selected Steve Zakuani for the 2014 season ( 2014 was a weird year, y’all). They’ve also seen players they’ve declined options for be drafted away, a notable one being Maxi Urruti in 2015. There are usually a handful of league veterans available in this draft, and there is a chance that Portland is active here to find a depth piece, so we shouldn’t be surprised if we seem them make a selection. The only complication being their place in the order — Portland is drafting in the 20th spot, and it remains to be seen how many impact players are still on the board at that stage.

January (likely 19-21) MLS SuperDraft

The annual draft of college soccer players hasn’t actually been formally announced yet, and it’s supposedly happening in a month. Fun times! According a report from Jeff Reuter & Sam Stejskal of The Athletic, the SuperDraft set to be held sometime in January 2021, likely on or around January 19 or 21. In addition, the draft is going to condense from four rounds to three rounds.

How it could impact Portland: The Timbers have never really had the reputation as a team that utilizes the draft to build their senior team roster, but they have found some major contributors via the process in the past. The two most obvious examples are Darlington Nagbe and Jeremy Ebobisse — one a bona fide Timbers star and the other an extremely solid player who is on the rise. Perhaps they can find another gem this year. The chances of finding similar talent will be complicated this year, as many collegiate soccer teams had their seasons canceled or postponed due to the pandemic. It is unknown at this time the draft order or when Portland will be selecting in the 2021 edition.

Sometime around the start of the 2021 season: Roster Compliance Deadline

Historically, MLS has set their roster compliance deadline on or around the start of the regular season. For reference, this year teams had until the day before the regular season started to be fully roster compliant. Deals can still be made as long as the league transfer window is open, but you can roughly expect the bulk of a team’s business to be done around the roster compliance deadline.

How it could impact Portland: There are still quite a few unknowns as it relates to the closing stages of the offseason. The exact start date for the new season is still to be determined (rumored to be early March), and the exact dates of the league transfer window have yet to be announced (usually January to March-ish). This usually coincides with the latter part of preseason games, so once balls start rolling onto the field, you can anticipate that most of Portland’s business will be done.


As we enter into this speculation-heavy period, there will be a lot of stories flying around about who Portland should acquire, who they are targeting, and how amazing/terrible a move is (some from yours truly). The reality is that we won’t know definitively what is what until the ink is dry and the team announces it, so the best we can all do is hold on, try to translate the league’s rules, and watch the silly season unfold.