2024 Portland Timbers Secondary Transfer Window Preview: Part 1

The Secondary Transfer Window opens on July 18th for MLS clubs. Several teams (LAFC, Houston, Austin) have already made some signings. Meanwhile, there is radio silence on the Timbers’ front. There have been some rumblings about a certain outgoing player (Dairon Asprilla, and I will cover his situation in an entirely separate article), but there have only been a few rumors about possible reinforcements in the summer. However, before those players can arrive, Ned Grabavoy and the rest of the technical staff have a huge decision to make.

The Right Path

New roster rules are coming to MLS this summer, and each team can choose one of two roster-building paths. Let’s take a closer look at both options with the current Timbers roster profile in mind.

Cascadia FC's Substack is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

The Centerpiece Path

3 True DPs/3 U22s

Grabavoy could choose to add another True DP in the summer. This would be possible because Felipe Mora is a Fake DP. A Fake DP is a player who is classified as a Designated Player for salary cap purposes and whose base salary is below the max-TAM line. In 2024, that number is $1,683,750. Per the 2024 MLSPA Spring Salary release, Mora is making $1.472 million. So he can be bought down using TAM during this transfer window and the Timbers can add a 3rd True DP. That begs the question: how likely is it that the Timbers add a 3rd True DP this summer? Would it make sense for their roster construction? 

The Development Path

2 True DPs/4 U22s/$2M GAM

If Grabavoy chooses this route, Mora would be bought down. The Timbers would then be able to sign another U22 Initiative player and have a boatload of extra allocation money to buy down other players currently on the roster or trade for another MLS player. The Development Path would give the Timbers additional flexibility and the ability to add more depth to the team rather than another star.

Team Needs

Now the question turns to team needs and what level of player the Timbers need to target to fill those needs. Is there really a need for another DP-level player on the team right now? The serious positions of need on the roster right now are striker, winger, fullback, and central midfielder. Mora is a Fake DP, and the team doesn’t need to invest in a player who would take a majority of his minutes. Rodriguez is a True DP and he’s looked best out on the left wing. Is a DP-level right winger a must-get in the summer? DP money should never be spent on a fullback, but there could be a case that a DP-level central midfielder will be needed in the coming years as Diego Chara continues to age. But do the Timbers need to make that move this summer? 

My Verdict

I think that Ned Grabavoy and the rest of the technical staff are going to choose the Development Path to continue building this roster. Even though adding another DP would be very nice, the Portland Timbers do not need another star in the summer. Multiple players coming in to boost the squad would be the best choice given the current state of the roster. Adding another True DP would severely handicap that. Plus an additional $2M in GAM could be used in inter-league trades. Now a new question arises: what position do you use the extra U22 Initiative spot on?

The New U22 Spot

Although MLS isn’t great at introducing new roster rules, the most impactful one the league has introduced in recent years has been the U22 Initiative. Players under the age of 22 can be signed from any other league and only carry a small ($150K-200K) salary cap hit. Transfer fees are not calculated into that cap charge either. Since the rule was created, the Portland Timbers have bought Santiago Moreno, David Ayala, Juan Mosquera, and Antony using the U22 Initiative. All of them have started games and earned plenty of playing time. It would make a lot of sense for Portland to add another U22 player in the summer. When I asked Ned Grabavoy about the new roster rules back in May, he gave this answer:

“As you go through the league, you don’t just build your roster through 6 months. It’s a collection of years and years and years and contracts that go into place. Even if the league does potentially come out with a new rule, and these look like pretty big ones in terms of giving more flexibility to teams with how they build, I think you’ll find a lot of teams may ultimately have to shift towards a model that gives them more ability to transition from where they are currently then just being able to say ‘We want to this, we want to do that.’ So there are some teams that are probably locked into that decision. I do think that we can make sense of a 2 DP and a 4 U22 model making sense for us but at the same time we will be open to a number of different things. I do think we’ve brought in some young players and if you look at the 4 or 5 younger guys that we’ve invested in, they have played important roles for us. And you look at players like Santi [Moreno] and others that have been here for 3 years and we don’t really see him as a ‘younger player.’ He’s given us some flexibility and some room within the [salary] cap but at the same time he’s playing a role for us every single game. He’s producing at a good level right now. We’ll continue to assess those things going forward but it will be interesting to see not just how Portland does it but how the league in general approaches potential restructure within the roster model.”

This interview took place 6 weeks ago, right before the Timbers played Seattle. At the time, the Timbers were winless in 8. Maybe his thinking has changed, but I think Grabavoy has already decided on adding a new U22 player. He wants that player to play an important role for the team, and there’s one position on the roster that would be perfect for a U22 signing.

U22 Striker

Let’s be honest, the Timbers’ messaging when Jonathan Rodriguez was signed pointed to the Uruguayan playing up top. But it’s clear that Felipe Mora cannot be dislodged from that spot if he is fully healthy. Rodriguez has also looked a lot better on the left than up top. What this Timbers team is crying out for is a tall U22 striker who can provide a different profile than Mora. Tega Ikoba is on loan at Indy Eleven this season with Hunter Sulte. While Sulte has been lighting it up (3 clean sheets and only 6 goals conceded in 9 starts), Ikoba has been seriously struggling due to injury and an inability to win the starting job. The Timbers Academy graduate wasn’t performing well with T2 in the past couple of seasons either. It was cool to imagine Ikoba as the striker of the future, but it’s nowhere close to Tega Time in Indianapolis this season. Investing in a young striker to supplement Mora would be an excellent use of funds this summer. But that’s only one need, so which position would be the next one to strengthen?

Depth/TAM Right Wing

I can let the cat out of the bag a little bit right now: Dairon Asprilla will leave the Portland Timbers this summer (that’s all I’m going to say on the matter for now). That opens up space for the Timbers to sign another winger in the summer. Rodriguez is holding down the left, while Santiago Moreno and Antony are battling for the starting right wing job. Moreno seems to be ahead in that race right now, but a few sources with knowledge of the situation have told me that a potential Moreno sale could be on the cards during the summer window. That would open up another U22 spot, but the Timbers should not use Moreno’s potentially vacant roster slot on another U22 player. What the Timbers need is a TAM-level winger to replace Moreno on the right. If Moreno doesn’t leave in the summer, a new depth winger should be brought in to compete for minutes and be able to play in case of injury. At least one new winger should be coming through the doors this summer, and there might be two if Moreno gets sold.

U22/TAM Defensive Midfielder

David Ayala’s emergence has been a wonderful thing to see over the past month. He has locked down a starting spot alongside Diego Chara, but there are questions about the players behind the two starters. Eryk Williamson has seemingly fallen out of favor, and could be a top trade candidate in the summer window. Cristhian Paredes has regressed after an excellent 2023 season, and might not be the right fit for Phil Neville’s system. The head coach has rested Chara for a couple games already in 2024, so another player can be added to the center of the park if Williamson is traded this summer. If no midfielder leaves in the summer, the Timbers could have the flexibility to add a new one during this window. In order to do so, Ned Grabavoy will have to get very creative.

Here is where the $2M in GAM from the Development Path can really come into play. Assume that the Timbers are already planning to sign a U22 striker with the new 4th U22 slot. In order to open a new one up, they would have to use GAM to move the player off of the slot. Ayala has the lowest base salary out of the current U22s, so it would be a lot cheaper to remove his U22 tag (to save GAM and to maximize the advantage of the U22 cap charge). With one player off the tag, it becomes possible to add another one. And if they do decide to add another one in this window, it will probably be a defensive midfielder. The front office could see defensive midfield as a higher priority position than striker (they’re wrong) but both should be filled during this summer with new U22 Initiative players. Keep in mind some of that $2M GAM and some additional TAM will be used to buy down Felipe Mora. In the offseason, they can reassess the need for a 3rd True DP. But at this moment in time, maximizing their GAM and U22 slots (reminder: U22s hit the cap at $150K for age 20 and under & $200K for ages 21-25) can help them save cap space while also adding more players who could contribute immediately. 

Fullback

After much consideration, I have arrived at a decision regarding fullback depth: it’s actually fine. Bravo and Mosquera are starters when healthy. Kamal Miller has been very solid at left back during a few games, and Eric Miller is a perfect backup right back. Yes, there is only one true left back on the roster, but I have also arrived at this decision due to a look at the entire organization. There are three intriguing fullbacks on the T2 roster: Jaden Jones-Riley, Sawyer Jura, and Blake Pope. Rather than signing another player, I think they should get a chance to play with the first team. Jura is still a couple years away, but Jones-Riley and Pope could hold their own in MLS if given the chance. Neville spoke about giving more academy and second-team players chances with the first team, and fullback seems like an excellent place to start. 

Thanks for reading Part 1! Part 2 is coming next week with a list of players that the Timbers should be targeting in the summer window, including some players that they’ve already been linked with. Thank you all for your continued support!

Cascadia FC's Substack is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.