New Year, Same Cycle

I spent the morning of January 7th, 2026 (Happy New Year by the way) putting some final touches on the 3rd part of the Offseason To-Do List. That article is still coming, by the way. Nashville won the sweepstakes for Cristian Espinoza (the Timbers reached the season finale of *insert reality TV show*). In order to proceed, it’s time to get familiar with the Cycle.

This is the Cycle. It never fails. Since the Timbers got whipped by San Diego by a scoreline of 4-0 in a sudden-death (double meaning to this phrase) playoff game, the Cycle has been stuck at “It’s Over.”

That’s not a terrible place to be. Sure, it absolutely stinks, but it’s far better than the next phase of the Cycle. Espinoza’s decision to choose Nashville didn’t move the needle in either direction. Popping bottles of champagne for coming in second isn’t something that should be celebrated, but it’s still a good thing that the Timbers were very close to securing Espinoza’s signature. Alas, he chose Nashville.

The Coyotes qualified for CONCACAF Champions’ Cup by winning the US Open Cup. Congratulations to them. But Espinoza’s choice isn’t entirely determined by the characteristics of the team. Nashville is a rapidly expanding metropolitan area with pretty good year-round weather. Some people prefer the sun instead of the rain.

Espinoza’s decision wasn’t a great way to start the day. However, he offered a test to the Cycle. Would the needle move if the top free agent declined the opportunity to come to Portland? It turns out that something earth-shattering would be the only way for the trusty “It’s Over” to morph into “It’s So Over.”

The differences between those two directions are stark. In order for “It’s So Over” status to be properly reached, catastrophic news must occur. Once again, the Timbers decided to tell a story.

In the real world, an ICE agent shot and killed a woman in Minneapolis today. This event did nothing to change the Cycle as it applies to the United States, who have been firmly stuck in “It’s So Over”-Land since November 2024. Coincidentally, the Timbers were also in “It’s So Over”-Land during that time period. Their most talented player threw a tantrum and would soon be on the way to a place that had a very important anniversary to celebrate yesterday. While the mayor of Minneapolis stood in front of reporters and told ICE to “get the fuck out of Minneapolis” (very strong and correct message), my mind was consumed by the Cycle. Espinoza’s test was over, but the ground began to shake again. The rumbling began at 7:12 AM, and it wouldn’t cease until 9:50 AM. By that point, the ground was unrecognizable.

One simple message moved the arrow.

It couldn’t be this bad. Surely some other news could be found. Maybe the announcement of Alex Bonetig, a new player that I’m very excited about (he has been announced as a Timber! Yay!). But this is how the possibility of David Ayala’s departure was raised: a run-of-the-mill image featuring Portland’s best midfielder in a jersey that he never wore on the pitch.

After confirming the legitimacy of the source, figuring out the fee became Issue Number One. Other thoughts were surely swirling around, but there was always a chance of two possibilities: Ayala would remain a Timber or the fee would be acceptable. Those were the only two options to completely avoid “It’s So Over”-Land. The arrow would be stuck in purgatory between the two negative aspects of the Cycle, but at least the extreme negative would remain untouched. But that arrow can only go one direction, and it received another nudge at exactly 9:00 AM.

This was all the confirmation I needed to see. Ayala would no longer be a Portland Timber. No word on the fee, but I spent 50 minutes trying to figure out how he would fit into Inter Miami’s roster.

Doing roster math for another team is very annoying, but Miami deserves special mention. Since winning MLS Cup in December, the Herons have been pulling out all the stops to re-tool their squad. Dayne St. Clair joined from Minnesota. Sergio Reguilon replaced the retiring Jordi Alba. The negotiating reached a fever pitch as the defending champs tried their hardest to bring top playoff goalscorer Tadeo Allende back to the club. None of these deals seemed to be illegitimate. The wider MLS world desperately wanted them to be illegitimate. But they won’t be getting their wish. It turns out that good soccer players are willing to take less money to play with the greatest soccer player. Miami’s one-man competitive advantage (in addition to selling players on the city itself) is something that makes them a wholly unique destination. Other teams simply can’t compete with that. It’s not a phenomenon entirely unique to soccer. Good football players (who always had evil in their heart) would take sweetheart deals to play with Tom Brady and the New England Patriots. In salary-capped leagues, the stars have power. Especially if those stars can provide a path to silverware.

After some more education on MLS roster rules from the very helpful Arman Kafai (his Substack should be required reading for any MLS fan) it became clear that Miami’s impending acquisition of Portland’s best midfielder would result in Ayala retaining his U22 status until the year he turns 26. He’s currently 23, but has one year left on his current Timbers contract. That’s potentially THREE MORE YEARS of team control with an incredibly team-friendly cap hit if he signs an extension. Such a bargain of a player must surely command a fairly large transfer fee, right? RIGHT?

Let’s run through the likeliest scenario at this point in time. At worst, Ayala isn’t willing to sign a contract extension. 2026 will be the last year that he plays in Portland. Even with a year remaining on his contract, his value is higher within MLS than in South America or Europe. That U22 cap hit is mouth-watering to any competent MLS general manager. U22s do not have a fixed acquisition price. Any amount of money can be spent to bring a U22 Initiative player to a MLS club. With those parameters in mind, I put a potential ACCEPTABLE price range between $7-10M. Surely that would be enough to satisfy a disappointed fanbase and front office. Alas, the ground kept shaking, and the next chapter could only be met by a phrase utilized by Charles Barkley when he learned of a “police presence” at a 2018 NBA regular-season game between the Houston Rockets and Los Angeles Clippers: “Are you kidding me?”

9:50 AM. Ground Zero. TWO MILLION AMERICAN DOLLARS for a player who recovered from two injury-plagued seasons and became a consistent beacon in Portland’s midfield. 

Two million dollars. Two million dollars. An amount of money that would completely change my current life around but counts as a drop in the bucket when professional sports come into play. Miami has struck the deal of the century. Their newest MLS-proven 23-year-old star will fill the hole left by the incomparable Sergio Busquets, who joined Alba in retirement after winning the biggest trophy of his career (MLS Cup, of course). The greatest defensive midfielder in a generation will be replaced by a Portland Timber. Busquets occupied a DP slot last season, but his replacement will have a cap hit of $200K and be 14 years younger. 

There’s a common phrase used to describe the rich. They keep getting richer and richer. There’s never an amount of money that can be comfortable for them. More money must be acquired. It can never be enough. When Miami’s front office was made aware of the possibility for Ayala’s arrival, they simply had to act. It was a deal that couldn’t be passed up. They had the roster space and the available funds. If you were in their shoes, you would’ve done the exact same thing. Such gluttony and greed will probably be on the horizon. But it’s nowhere in sight at the current moment.

Two million dollars for a player of Ayala’s quality is a laughable return. Despite the pressures of an expiring contract, the Timbers decided that taking a fee (any fee) would be better than losing him. It’s a good move from a business standpoint. However, I expect the $2M to be converted to GAM. The Timbers ended the 2025 Summer Transfer Window with a total of ZERO dollars in GAM. More GAM allows for more roster flexibility, and the Timbers could really use that allocation money to finance a new defensive midfielder. They already needed to add one prior to Ayala’s departure. Now they need to find TWO players to fill the most important position on the pitch.

Could there be an extenuating circumstance here? Was Ayala’s desire to play with Lionel Messi forcing the Timbers’ hand? Let’s not ignore the fact that Messi is a God in Argentina. Every single Argentine would be foaming at the mouth to play with him. That’s just a fact. Miami’s proximity to South America is another selling point. Ayala’s ability to be closer to family could be higher on the priority list than the opportunity to play with his biggest idol. Portland’s location makes a trip home incredibly complicated. Is location at play again, just like it was with Espinoza?

Those are questions that should be answered in the coming days or weeks. They will need to be answered, because this is another moment of horrific optics for an organization that is very familiar with that genre of events. Last year, Ayala was adamant about wanting to stay in Portland. “I can honestly say I feel like I’m home,” Ayala told Adam Susman in August. But “home” is not the same as “Home.” 

There is a humiliation factor to this deal. For the second consecutive year, the Timbers have sold one of their best players to another MLS club. The primary message from ownership and the front office has revolved around “competing.” It is very hard to compete when other MLS teams are snatching up your best players for pennies on the dollar. Evander’s situation is vastly different than Ayala’s (no temper tantrums have been reported) but the $12M fee Cincinnati paid Portland eleven months ago resembles a bargain. That $12M did jack squat in the playoffs, but back-to-back MVP quality campaigns speak for themselves. Evander’s story is well-known by now (at least one version of it) but it still does nothing in regards to optics. It still looks like the Timbers couldn’t keep their star player happy. Well, according to the experts on Apple TV, who are famously well-versed in their knowledge about every MLS team. 

Santiago Moreno’s cowardly flight resulted in $6M coming Portland’s way, but it was another optical nightmare. Some teams are able to lose their best players with sadness but also appreciation. 

It is so hard to be appreciative of this deal given the sudden change in fortunes from last August and the measly return. I’m happy for Ayala, who will get the chance to play with his idol. I’m happy that he’ll be able to be closer to his family in Argentina. I’ll save the remainder of my player-specific thoughts for an upcoming article. He deserves more than a few sentences. 

On the international soccer stage, Portland can only sell itself to a certain extent. It’s very far from South America, and Europeans would sooner consider southern cities with nice weather instead of Portland. This is a familiar story if you want to pivot to another professional sports team playing in the Rose City.

Not the Thorns. Are you kidding me? They’re still a destination club for the top players in women’s soccer. Well, that’s what they should be regarded as. 

I’m talking about the team that plays on the other side of the Willamette. The Portland Trail Blazers do not have a good track record when it comes to signing free agents. When their all-world point guard was at the peak of his powers, their second-best player decided to go south. After all, he was from Texas, and the Beaver State is very far away. That same generational point guard refused to run from the grind. Despite carrying a team stacked with role players, he routinely brought them to the playoffs. Their zenith was a Western Conference Finals berth in 2019, where the star-laden Golden State Warriors slapped them around. Despite having an arena that never falls silent, and a city rabid for their success, the top players would never consider the Blazers when free agency came around. It was simply too far removed from the rest of the country.

The Timbers suffer this same fate, but on a different scale. Diego Valeri and Diego Chara fill the same role as Damian Lillard. The ones who stayed and refused to run from the grind. The ones who embraced Portland, a city that is rarely loved by high-profile athletes, and made it their home. I fell to my knees in a Costco when Lillard was traded to Milwaukee. I am not a Blazers fan. But I am a Portlander, and his departure hurt. 

Miami Heat fans desperately wanted Lillard to join their tax-evading haven in South Beach. Blazers fans, who were prepared to see the prodigal son leave his adopted home, tormented them relentlessly when the deal was announced. Three years and four months later, Miami got their revenge. Unlike Lillard’s departure, this one came completely out of the blue. As a result, it’s going to hurt seeing Ayala put on a pink Miami jersey and lead the Herons to a CONCACAF Champions’ Cup title. I’ll keep rooting for him. That isn’t controversial.

Phil Neville’s contract expires at the end of the season, and his squad just lost their most capable midfielder. Ayala will need to be replaced as soon as possible. A U22 spot has just been opened, although everyone wishes that it was still full. But the Soccer Blazers are about to do it again. They’ll have to convince another excellent player that Portland can become home. In the meantime, the humiliations will continue.

For the third transfer window in a row, the Timbers have parted with one of their best players. It’s an utter travesty that the Timbers will need to rectify with haste. After all, the Cycle can only go in one direction. “It’s So Over” eventually morphs into “We’re Back.”

The Timbers open the 2026 season in 45 days. Their offseason to-do list just got longer. Just what they needed. Their continued ability to humiliate cannot be defeated. Each positive moment prolongs the humiliation. The starboy will play with stars as the Timbers try to add another star to their crest. The Cycle keeps spinning.