The month of May 2012 concluded with a stunning U.S. Open Cup loss to an amateur club called Cal FC, which had been formed earlier that year. Adding insult to injury, that defeat occurred at home, in front of a crowd that, like those in Washington DC, Toronto and Seattle, had set a new standard for MLS support. The summer was approaching, and the foundation established by the Portland Timbers the year before, during a competitive inaugural MLS campaign, appeared to be crumbling. Several signings weren’t working out and coach John Spencer was struggling to keep the team afloat.

The Timbers entered June 3-7-4 in league play.

Gavin Wilkinson understood the fragility of the situation and knew there was only one way to fix it: work harder. The Auckland native had parlayed his vast reserves of elbow grease into a productive playing career that spanned 15 years and four continents. He never was the quickest or most technically gifted, but he was smart, relentless and always eager to get stuck in. Capped 38 times by New Zealand, Wilkinson played and coached for the Timbers’ United Soccer Leagues (second tier) team and added ‘general manager’ to his list of titles and responsibilities in 2007. There couldn’t have been anyone who spent more time at the old stadium on SW Morrison Street than Wilkinson. But in June 2012, he decided more time there was exactly what was needed.

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So he bought a condominium next door.

“I think I was working 18-19 hours a day in the office already, and we were living about 30 miles from the stadium. I had a very, very forgiving family. I purchased the condo and they could come see me on the weekend,” Wilkinson, 42, told SI.com this week. “There was a bed in there and that was about it … It’s the best investment I’ve ever made.”

And not just because of rising real estate prices. It was that sort of devotion and commitment to getting the job done, to turning over every rock and taking every bit of responsibility, that left Timbers owner Merritt Paulson with no doubt that Wilkinson remained the man for the job. The Kiwi retained his position as Timbers’ GM when Spencer was fired in July 2012. Wilkinson then was instrumental in recruiting current coach Caleb Porter, who signed on the following month and finally arrived in Portland after the 2012 season. While laying the groundwork for the Timbers’ rebirth with Porter, who finished out the year at the University of Akron, Wilkinson coached the team.

There was a vocal segment of Portland’s fan base that wanted Wilkinson to join Spencer on the unemployment line. The “GW Out” banners weren’t hard to find in the stadium’s raucous north end, and more than 82% of the respondents to an unscientific Nov. 2012 survey in The Oregonian advocated for Wilkinson’s dismissal. But Paulson, who purchased the team in 2007, Wilkinson’s first year as coach/GM and his seventh with the organization, never considered it.

“It takes a strong personality to remain loyal in the face of adversity,” Wilkinson said.

Now the owner’s faith, and Wilkinson’s desire to go the extra mile, has paid off. Over the past three years, only three MLS teams have a better regular season record than the Timbers. And Portland is one of only two (the New York Red Bulls are the other) to advance as far as the conference finals twice during that same span. The organization’s under-23 team and its women’s team, the Thorns, already have won championships under Wilkinson’s watch. Now the senior squad has its chance in Sunday’s MLS Cup final against the Columbus Crew.

“He’s a case study in why you never let fans vote on a GM. Fans are going to have an opinion, but they get one look: from the outside in. They never get the whole picture,” Paulson said, backing his colleague while taking the opportunity to have a dig at his rivals in Seattle. “The more I got to work with Gavin, and I think he was a good coach, but what particularly impressed me was his business mind and his eye for talent … He never had a formal college education, but he’s extremely tech savvy and was an early adopter of every kind of new technology. He’s great with spreadsheets, budgets—he’s very quantitative and good with contracts and legalese and can find loopholes in just about everything. And the overriding trait: he works night and day.”

Don Ryan/AP

The son of a baker and a mother who worked in catering and cleaning, Wilkinson grew up loving soccer in a rugby-mad country.

“If you didn’t play rugby, you were always fighting a battle for relevance,” he said.

Wilkinson represented New Zealand at the junior level and turned pro at 19 with Waitakere City. He then spent time in Western Australia with Perth Glory before moving on to clubs in Hong Kong, Singapore and Ireland. He won the 1998 Oceania Nations Cup with the All-Whites and played for New Zealand at the Confederations Cup the following year. Coincidentally, the U.S. squad he faced during the group stage in Mexico included Columbus soccer icons Brian McBride, Frankie Hejduk and Brad Friedel and current Crew coach Gregg Berhalter.

Wilkinson was out of contract in 2001, when agent with U.S. connections made inroads with two second-tier teams: the Charleston Battery and Portland Timbers. The latter were returning to the field after a decade’s hiatus. The opportunity to start fresh appealed to Wilkinson and his fiancee (now wife, Heather), and he signed a three-year deal with the reborn club.

“We decided to make the jump,” he said. “You could see the relevance the team was starting to evolve and there was tremendous support from fans and the city in general. It was basically the birth of a new era of soccer in Portland in many ways.”

Wilkinson may have been a bystander at the birth, but he played a massive role in soccer’s modern upbringing in the Rose City. He helped lead the Timbers to the USL’s equivalent of the Supporters Shield in 2004, became a player/assistant coach in ’05 and then in ’07, after retiring as the team’s all-time appearance leader, he took over as head coach and GM. Meanwhile, because that wasn’t enough, he launched and ran a youth club called Eastside Timbers based in suburban Gresham, Oregon.

That was his formal education.

“I was always looking for something else to work on and starting a youth club is no small task and I suppose in some way, that was my training in some way. The budgeting process, the legal aspects of soccer in general—that’s a whole different side of the game,” Wilkinson said. “With the Timbers, before Merritt took over the club it was month by month. There was a lot of talk about the Timbers not existing, about the Timbers folding, and we were making a go of it anyway. It involved a lot of partners in the community to keep things ticking over.”

Wilkinson watched the budget closely.

“We didn’t have a lot of resources on the soccer side. Everybody wore two hats,” he said.

Portland finished the USL’s best regular season record again in ’09, and Wilkinson twice was named the league’s coach of the year.

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“It’s just something I enjoy—the challenge of putting together pieces in different ways, whether it’s helping on the field or off the field with the budgeting process. It was just another problem to solve, and the general consensus if that if you work hard enough, you can eventually figure it out,” he said. “Over time, you start to critique your own way of doing it and you [refine] the process and the outcome.”

Paulson’s investment and the club’s 2011 ascension to MLS raised the stakes, the profile and the budget, so Wilkinson focused on GM duties while Spencer coached the team. Wilkinson had pushed for a long-term contract extension for the Scot, but it was clear by the middle of 2012 that sticking with Spencer was a mistake.

“When it was clear it wasn’t working, Gavin owned up to it,” Paulson said. “There was more pressure on him to get it right with the second hire, and we did.”

The rebuild was a testament to Wilkinson’s connections, his tireless pursuit of leads in unlikely places, an ability to live out of a suitcase and his chemistry with Porter. The manager lets the GM do the digging and crunch the numbers, while the GM yields to manager’s vision for what his team should look like on the field. Both said that they see the game similarly. Both acknowledged that they’re restless.

“I’m a total grinder. I’m thinking all the time and I’m texting him all the time and if I had a GM that wasn’t working long hours, that wasn’t a grinder, that wasn’t trying to beat the bushes and make us better, I think there’d be some friction,” Porter told SI.com. “We have the same goal in mind and his skill set in looking to find players and to manage the cap complements my skill set.”

Will Johnson arrived prior to the 2013 season while playmaker Diego Valeri joined on loan, then inked a deal with the Timbers that August. The Argentine proved to be a seminal signing, and Portland finished first in the West and before falling to Real Salt Lake in the conference finals. The on-field bounces went against the Timbers the following season—they missed the playoffs by a point—but the core of an MLS Cup finalist was fleshed out with the acquisition of defenders Liam Ridgewell and Jorge Villafaña and striker Fanendo Adi. Last winter, the likes of defender Nat Borchers, midfielder Dairon Asprilla and goalkeeper Adam Kwarasey completed the puzzle. None, save Borchers in Salt Lake City, was a household name. Yet they’re all 90 minutes from being champions.

“The big strength of a successful pro club is the collective marriage,” Porter said. “Gavin is really good at finding options and then ultimately, I’ve figured out which options are the best option.”

Wilkinson, with Porter’s input, has developed complex criteria that current and future signing (succession always is an issue) must meet. There are checklists and spreadsheets—both Porter and Paulson mentioned the spreadsheets—and a 120-page performance plan that defines job and position requirements, scouting, signing and player acclimation procedures and club protocol. Wilkinson is especially fond of loan-with-an-option-to-buy deals, such as the ones executed with Valeri, Adi and Alvas Powell, and negotiating creative trades with MLS rivals. He manages 18 separate budgets covering the MLS, USL, PDL, NWSL and academy teams and is in the process of looking for a youth technical director and a head of scouting. Mark Parsons was named Thorns head coach in October. Wilkinson's days as a one-man band are ending, and he's now transitioning to oversight of a small soccer empire.

There are members of the Timbers Army who remain unsatisfied. “GW Out” still makes the occasional appearance in the north end. Perhaps that’s the price of passion. Paulson said that Wilkinson has become “the poster child for protest—if he wasn’t here, it would be someone else.” Porter said, “If I was here 15 years, I’d be getting ‘CP Out’ signs.” Some fans believe there have been enough false starts and enough failed signings to warrant a different direction at the top. Others remain angered by the club’s effort under old ownership to create a “family friendly” supporters group that some thought was designed to undercut the TA. Wilkinson, who was asked to wear that hat as well, said that was never his or the Timbers' intention. Porter and Paulson believe the unrest is confined to a small minority. Most fans, they said, understand the challenges of building a consistent MLS winner and realize they’re starting to establish that very thing in Portland.

GW isn’t going anywhere. There aren’t many men in MLS, in any position, who’ve been with the same club for 15 years. He’s certainly proven his worth to Paulson, who speaks about his GM in both defiant and deferential tones.

“The guy bleeds green,” Paulson said. “He gives everything he has and we truly believe he’s one of the best, if not the best, GMs in MLS. He knows a lot of fans appreciate him.”

Wilkinson also knows how long they’ve been waiting for a championship. The Timbers fell short in the NASL’s Soccer Bowl in 1975 and haven’t played for a league title since. The club is looking into the construction of a memorabilia and trophy display at Providence Park, and despite all the history and tradition surrounding the organization, there’s been frustration at the final hurdles. If the Timbers can cart home that big silver cup from Columbus, it wouldn’t necessarily lighten Wilkinson’s schedule, but it might help him garner the appreciation that Paulson and Porter think he deserves.

“It would be validation—validation for the fans, for the front office, for the coaching staff,” Wilkinson said of a potential MLS championship. “It would show that there is true passion and belief and intelligence behind what is happening. It would align everything. To say that the Timbers are one of the best teams in MLS is something we’d like to hear on a regular basis, and it’s something we know we’ve got to work very hard to maintain…There are a lot of people in this organization that understand what this team means to this city and who want to help this team be successful. It means an awful lot to a lot of people.”