In the summer of 2012, back when regular trips to MLS Cup were nothing more than a pipe dream for the Portland Timbers, Gavin Wilkinson kicked himself out of his own house.

The Timbers were at the lowest point of their MLS existence. They had just fired manager John Spencer, and Wilkinson, who coached the club from 2007-2010 in USL, was reluctantly pulling double duty as both GM and interim head coach. The added responsibilities made his 45-minute commute from the suburbs to the Timbers’ downtown stadium impractical. He was working 20-hour days; an hour-and-a-half roundtrip in the car simply wasn’t going to work.

So, Wilkinson packed his things, left his wife, two kids and their family home outside of Portland and moved into a newly-purchased condo right next door to Providence Park, then called Jeld-Wen Field. Apart from the weekends, when his family would stay with him at the one-bedroom home, he essentially lived at the stadium. Training, film review, sorting through contracts, identifying transfer targets and running a coaching search that would eventually end with the club hiring Caleb Porter were his existence. Everything took a backseat to the Timbers.

On a personal level, it was hell. Wilkinson barely saw his family, worked himself into the ground and had his job repeatedly and loudly called for by significant sections of the Timbers fan base, all for the pleasure of compiling a woeful 3-8-6 record as interim manager.

On a professional level, it might have been the most important period of his career. Wilkinson and the Timbers were at an inflection point that summer. They didn’t make the playoffs in their inaugural MLS season in 2011, but the team did well enough for owner Merritt Paulson and Portland supporters to expect a postseason berth in their second year in the top flight. But instead of taking a step forward, the Timbers backslid in 2012. By the time Spencer coached his last game in early July, Paulson and Wilkinson knew their club needed an overhaul. If they got it right, they felt they could become a consistent MLS contender. If they got it wrong, they feared they’d become an also-ran.

Wilkinson knew he’d only get one more chance.

“We had made mistakes,” he told MLSsoccer.com this week. “And I couldn’t make the same mistakes twice.”

An Unexpected Ascension

Six years after their summer of discontent, and it’s pretty clear that he hasn’t. Wilkinson and Portland have grown together. The 28-year-old who signed with the lower-division Timbers in 2001 as a journeyman defender looking for one last shot has become one of the better GMs in the league, a 45-year-old club legend who navigated Portland’s uncertain MLS beginnings and has the team looking for their second MLS Cup title in four years on Saturday at Atlanta United.

“He’s the best GM in MLS,” said Paulson.

Photo: Ray Terrill

There’s no one path to becoming an MLS GM, but most of the league’s chief soccer officers share a common characteristic or two. Many are American, many played in MLS and many earned a law or business degree at an elite university. Others spent time working in the league office or as agents. A couple cut their teeth at big-name foreign clubs or in a national federation.

Wilkinson’s journey doesn’t fit in any of those boxes. The New Zealander never played in MLS, never attended college, never worked as an agent or at league HQ and didn’t spend time with for any foreign clubs of significance. He has, however, always wanted to run the sporting side of a club. And he’s always put himself in position to do so.

When he was playing in Australia with Perth Glory in the late-90s, he picked up a part-time job with the club as a development officer. He liked working in the front office, but he had to put that life on hold for a couple years while playing for clubs in Hong Kong, Singapore and Ireland. He dove back in after he signed for the reincarnated Timbers ahead of their first USL season in 2001, co-founding Oregon youth club Eastside United that same year. For Wilkinson, creating a successful club – Eastside United, now known as Eastside Timbers, a Portland academy affiliate that remains one of the top youth programs for boys and girls in Oregon – scratched an itch that being a player simply couldn’t.

“I loved the idea of trying to help build something where you not only leave a legacy, but where you create something that has the potential to give back for a long, long time,” he said.

Helping run Eastside was Wilkinson’s first real brush with building an organization. He was hooked, and his experiences on the youth level cemented his desire to one day run a professional club. After six seasons as a Timbers player, the final two of which were spent as a player-assistant coach, he got his chance. Wilkinson was hired as Portland’s head coach and GM after he retired following the 2006 season. Paulson bought the team a few months later. Wilkinson had plenty of success on the bench, winning USL First Division Coach of the Year in 2007 and 2009 and leading Portland to the USL regular-season title in the latter season.

There was only one catch: He didn’t love coaching like he loved being a GM.

“I think it’s just the way I’m wired,” he said. “When you look at what I did with starting a youth club and then helping the USL team in Portland be viable, it was always managing budgets, managing contracts, managing infrastructure, organizational charts, staffing, absolutely everything involved with building it out and targeting how we can get better in every department. It’s just the problem solving – I love it.”

So, after the Timbers were awarded an MLS expansion franchise late in 2009, Wilkinson let Paulson know where his heart lay. He wanted no part of coaching the MLS team. He wanted to build it, instead.

Struggle, refinement & foundation

Paulson gave Wilkinson the gig, naming him technical director for the MLS Timbers in January 2010 and keeping him on as coach for the club’s final season in USL.

Portland had a solid first year in MLS in 2011, remaining in playoff contention until the final week of the season before ultimately missing out on the postseason by four points. Wilkinson didn’t have any scouts on staff and was forced to lean heavily on recommendations from agents and consultants to point him towards transfer targets, but he managed to sign Diego Chara out of Colombia, land Darlington Nagbe in the SuperDraft, nab Jack Jewsbury in the Expansion Draft and trade for Rodney Wallace that first season. For a club that wanted to field “a young, athletic, attack-minded team,” that wasn’t a bad base.

It also wasn’t enough. Wilkinson said that he and Spencer didn’t think strategically enough about their system. How, exactly, does a “young, athletic, attack-minded team” play? What characteristics does the striker need to have? What qualities do you need from a right back? How do the players and their contracts fit together?

Those questions went mostly unanswered, leading to a misshapen roster in 2012. Designated Player striker Kris Boyd wasn’t a fit; hyped prospect Jose Adolfo Valencia arrived injured and never contributed; the backline gave up the third-most goals in the league.

After Spencer was fired, Wilkinson and the Timbers went further into that process. New protocols were implemented. A clearer vision was articulated. The way they built their roster became more focused.

“There was a deeper dive to can we refine the vision of the club, can we refine the philosophy of the club, can we put metrics with it and can we hone in on those metrics and make sure that every part of the club is connected,” said Wilkinson. “In saying that, it sounds very simplistic, but it’s a lot harder to implement.”

That implementation began in late August 2012, when the club announced that they hired Porter away from Akron University. His addition set the table for perhaps the biggest move in club history: Signing Diego Valeri. Wilkinson and the Timbers landed the playmaker on loan from Argentine club Lanus in January 2013, just one month after they acquired midfielder Will Johnson in a trade with Real Salt Lake. Both players were huge in their first season with the Timbers, each earning a spot on the MLS Best XI as Porter led Portland to a surprise first-place regular-season finish in the West.

They ended up getting bounced by RSL in the Western Conference Championship series, but 2013 set the foundation for Portland’s future successes. Wilkinson had a model in place, had a coach he was confident in, had an MVP-level star in Valeri and one of the most underrated Designated Players in the league in Chara. It took a couple of years of trial and error and some patience from Paulson, but Portland and Wilkinson had found their groove.

“I think there are certain signings that change the direction of the club,” said Wilkinson. “I think Diego Chara did, I think Diego Valeri did, I think Liam Ridgewell did. I think there are moves when you start to say, ‘OK, we’ve solved that position for the next two, three years, now let’s solve this other one, but make sure the all work together.’ And when you’re able to get a lot of decisions right from the playing personnel and the coaching personnel, you don’t have to solve those problems. You start focusing on other things.”

For Wilkinson, “focusing on other things” meant building out his scouting staff, creating new infrastructure around the first-team, building the Timbers’ USL side, T2, and launching the club’s successful NWSL team, the Portland Thorns, who he still spends “20-30 percent” of each workday on.

It also, of course, meant continuing to add talented players. Wilkinson has a good hit rate with his biggest signings. Ridgewell, striker Fanendo Adi and Jorge Villafaña were added in 2014, Nat Borchers came in 2015, Sebastian Blanco and David Guzman arrived in 2017. That new blood led to some excellent results for the Timbers, who, though they missed the playoffs by one point in 2014 and two points in 2016, made a late-season run to win MLS Cup in 2015 and finished with the best regular-season record in the West last year.

“I’d say he’s brought in two of the greatest signings in MLS history in Diego Chara and Diego Valeri,” said Paulson. “And both were clearly his guys. It’s always a collaboration and we’re working with the coaches then as we are now, but I can tell you those were Gavin Wilkinson signings. And you look at guys like Fanendo Adi and Blanco and Ridgewell, who I think is going to go down as a really impactful signing on the defensive side, he’s largely gotten our big signings right.”

How they got here (again)

This winter, Portland and Wilkinson hit another inflection point. Porter abruptly left the club last November, throwing the Timbers into a surprise coaching search. Wilkinson once again ran point, leading the way on an exhausting three-week process that led the Timbers to Gio Savarese.

It’s still relatively early in Savarese’s tenure, but that hire has so far only led to more success, as have Wilkinson’s roster moves. The GM traded Nagbe to Atlanta in a blockbuster deal last December and kicked the process of finding successors for Valeri and Chara, both 32, into higher gear. He used some of the allocation money acquired in the Nagbe deal to sign midfielders Andy Polo and Cristhian Paredes, both of whom have contributed this season. Portland also brought in big-time Argentine attacking prospect Tomas Conechny over the summer. He hasn’t contributed to the first team just yet, but the Timbers are high on the 20-year-old. The Timbers need those youngsters to step up or else the club will have to find new stars if they want to continuing competing once age inevitably starts to catch up to Valeri and Chara. Wilkinson knows that, and he’s already preparing for that difficult eventuality.

But a little extra work is nothing new for the Timbers lifer. Wilkinson knows how rare his 17-year run with Portland is. He knows he’s on his third or fourth life in Portland, and he’s incredibly appreciative that he’s had such remarkable longevity with the Timbers.

“The fact that I’ve been able to be in one spot for so long is incredible and it’s unique and it’s enjoyable,” he said. “When you look at how long I’ve been with the Timbers, it’s basically three life cycles relative to professional sports, and that’s so rare. I joke within the family that it’s good to defy logic and try to prove people wrong, and the whole thing about 2011 and 2012 and failing then and again failing in the first part of 2015, was that I was given the bandwidth and had the confidence to fix it collectively with other people. I think that’s incredible and it’s certainly made it more enjoyable.”

That gratitude doesn’t come without pressure, however. Wilkinson, who’s generally averse to public praise, knows how fickle sports can be. A genius one month is a fool the next depending on how certain moves shake out.

He understands that, of course. Fortunately for Portland supporters, Wilkinson, the man who once put himself in self-imposed exile in an effort to fix his club, only knows one way forward: Give more to the team that has given him so much.

“He just bleeds it. He just cares about it so much,” said Paulson. “I think if every fan could see what I see, if they could see how much the Timbers mean to him, what the club means to him, he’d be the most beloved guy that we’ve ever had.”