PORTLAND, Ore. – That little of the information was particularly new kept the mood at Providence Park light on Tuesday afternoon, giving attendees of the Portland Timbers’ season-ending media availability a chance to embrace the contrast. Ten-and-a-half months earlier, team general manager Gavin Wilkinson and Timbers’ head coach, Giovanni Savarese, were joined by Portland’s newly-confirmed technical director, Ned Grabavoy, to provide final context around an MLS Cup-final run. This year, it was only Wilkinson and Savarese, and they were reflecting on disappointment.

The 2019 Timbers made the playoffs for a third year in a row, but what’s become clear in the 10 day since the team’s season-ending loss at Real Salt Lake in Round One of the Audi 2019 MLS Cup Playoffs was that postseason was no longer enough. Seven hours after the press conference, with Seattle Sounders FC celebrating a Western Conference title in victory at Los Angeles FC, the sense of lost opportunity would feel more acute, adding new vitality to one of Wilkinson’s shortest press-conference responses.

“Yes,” Wilkinson had said early and definitively to the session’s third question, having taken a beat to pause and inhale. The inquiry had come from The Oregonian’s Jamie Goldberg, sitting in the room’s front row, asking whether the Timbers had been impacted by “outside distractions.”

The Timbers finished 2019 in sixth place in the Western Conference, in the same vicinity the team had the year before, when they finished fifth. The feeling at year’s end, though, was markedly different.

“(It’s) the honest answer,” Wilkinson said, before explaining, “But there’s always going to be something. In sports, you’re always managing something.”

Portland’s somethings started around the same time as last year’s season-ending press conference, when management was already struggling to assess the impacts of their Cup run’s downside: a short offseason. Decisions on contracts and player futures were being finalized on the flight home from Atlanta, where the December 8 game left the team with roughly six weeks before preseason opened.

With holiday expectations crammed into that period, players knew the offseason would feel short. It became the 2019’s first distraction. Soon after the team was back, they were off to Costa Rica for two weeks, then Arizona. The 12-game road trip that followed added to the distractions, though on June 1, with the team’s first home game, those were supposed to end. Instead, amid fan discontent over new league policies, the unexpected absence of the team’s newest star, media reports about contract negotiations and the schedule congestion of the season’s second half, distractions continued to mount.

“If anything, it’s been a challenging year,” Wilkinson conceded. “We know that. There’s been a level of exhaustion that hit everybody.”

And yet, come the end of the regular season, the team was in a similar position to 2018: primed to make a playoff run, albeit from an underdog's position. Within the two weeks that linked the regular and postseasons, though, the feeling wasn’t the same.

“Last year, when we arrived at this stage, we felt very fresh,” Savarese admits. “We felt like the season still was early. This year, (with) everything that we had to go through, even though the group was still united, I think there was a lot that we had to handle. I saw the group was a little more tired.”

In hindsight, none of Portland’s obstacles feel insurmountable. Even taken as a group, the challenges seem like the type sports teams are expected to navigate. As Wilkinson said, this is sports; it’s always something.

That 2019 was ultimately defined by those somethings has to prove motivational, and in the changes that will come between now and the new season, the whys of 2019 should loom.

The uncertainties of the squad

On Tuesday, the focus of many of those changes concerned some of 2019’s standouts, where the ongoing uncertainty surrounding the team’s captain, Diego Valeri, briefly capturing centerstage. With the team’s CEO and owner, Merritt Paulson, having spoken publicly about the contract negotiations five days prior, neither Wilkinson nor Savarese could offer new information, though each had their chance to speak on the biggest issue hovering over the Timbers’ offseason.

“There’s the desire to make sure that [Valeri] stays,” Savarese said. “That’s why we’re having conversations, and we’ll see. There’s talks. There’s all the effort to try to get to that place.”

“Without going into too much detail,” Wilkinson had said before, “it’s been made very, very clear that the club respects and loves (him) in every capacity. He’s somebody that’s we’ve acknowledged that’s been instrumental in the club’s success and is a talented player.

“On the other side, I would say that it has to be what both parties want. I don’t hold all the information to make that determination.”

Important questions also loom around forward Brian Fernandez – who Wilkinson said is back working out in Portland while still part of Major League Soccer’s Substance Abuse and Behavioral Health program – and goalkeeper Steve Clark, whose contract expires at the end of the 2019 season. According to Wilkinson, “[Clark] is a player that there will be a bonafide offer made to,” allowing the Timbers to maintain the player’s MLS rights.

“It’s a player that I’m in constant contact with the agent,” Wilkinson said, “and we are hopeful Steve is back for next year.

“He’s part of the equation. We’re part of the equation. We hope that we solve our part and make sure that he feels respected and this is a club he has to continue with.”

Jorge Moreira, the team’s right back who is on loan from River Plate in Argentina, will “be with [Portland] for at least another six months,” Wilkinson said, adding the Timbers are “looking for a solution to keep him [with the Timbers] for several more years.” Meanwhile, the process of finalizing Cristhian Paredes’ move from Mexico’s Club América continues, with club hoping to complete the Paraguayan loanee’s permanent transfer.

That move, though, and the club’s option to buy the player, dovetails with the decisions around other players, including Valeri. According to Wilkinson, Parades’ current buy option would impact his status as a Designated Player, albeit a “Young” one (around which there is a separate, less-expensive set of rules).

Each MLS team is allowed a maximum of three Designated Players each season, with only $530,000 of their total salary hitting the team’s salary cap, no matter the player’s true salary, according to last year’s roster rules. For Young Designated Players – who can be no older than 23 in a given league year – the roster charge is only $150,000. Last year’s total salary budget was $4,240,000 per team.

“The DP slot will be used on the forward position or the winger position,” Wilkinson said when asked a hypothetical about a potential open Designated Player spot. The team’s GM had always confirmed the list of targets shared by Paulson: fullback, centerback, midfielder, winger and forward. The latter two tend to carry the highest costs.

”What we need is the flexibility within the budget to be able to make the moves necessary short-term and long-term to be successful,” Wilkinson explained. “What we don’t want to do is tie up three DP slots and find ourselves in a marketplace where we can’t afford or fit in the winger or forward within the cap that we have …

“There’s also an option to purchase Paredes. We’re trying to structure that so he is no longer going to be a Young DP … there’s all these moves within the roster, and we need flexibility.”

Framing 2020

One DP issue taken off the table on Tuesday surrounds Sebastián Blanco, with a new multi-year, Designated Player contract for the player made official on Tuesday. Add an impending expansion draft to welcome incoming teams from Miami and Nashville, along with the regular player options and potential trades that emerge each offseason, and the issues around the team’s 2019 holdovers coming into view.

In contrast, the news around 2020’s potential arrivals may end up swept under the rug, left to rest until the biggest stories from 2019 are resolved. At the onset of the press conference, though, Wilkinson and Savarese confirmed that they’d just returned from Europe, where they had completed the next stage in acquiring one of the club’s first offseason targets.

“For us, [the trip] was focusing on one specific player, where there were meetings with the player, meetings with agents and clubs, and just seeing if we can come to a resolution,” Wilkinson said. “We’re optimistic that one will [work] out, but we still have a lot of work in front of us.”

Two or three of this offseason’s acquisitions would be expected to compete for starting spots immediately, Wilkinson said, while the team’s fullback signing was in the process of being finalized.

“We have a young right back that the formality is still completing some of the paperwork and the transfer agreement,” he said, “but by and large, that deal is done.”

As new signings happen, the typical lessons from a previous season come into view. Where was the squad weak, or thin? How does the team need to evolve? Who has earned a new, bigger commitment, and who is set to depart? Every team deals with those questions each offseason, but for the Timbers, there’s an additional layer to break through – the fog from a season of unanticipated obstacles.

Just as the players had to manage more than expected during the 2019 campaign, so now will the technical staff, trying to build toward 2020, have to deal with the lessons from a strange season. There are lessons, there, but biases, too. If 2019 truly was a singular, outlying season, the knowledge Portland can gain will be harder to come by, let alone apply going forward.

Even as the next year emerges, last season remains in focus. Ten days from the Timbers’ last game, it’s too soon to move on.