During five years of bank ownership, the golf course turned brown, the native areas between the holes overgrown and unruly. Membership dwindled and the course opened for public-fee play just to keep the club afloat.
It barely survived.
But once the economy levelled a bit, Winchester's new owners took a novel approach to help it rebound: They sank more money into it, hoping a more luxurious club would drive up the real estate and, in turn, make the club more appealing to potential members.
"Nobody believed that you could turn this thing around and make it vibrant again because there were so many things that needed to fall together to make that happen," said David Bennett, Winchester Country Club's general manager. "We kind of had to do a dance to choreograph this all to make it work."
Winchester's plan worked. Other country clubs weren't so fortunate.
In the late 1990s through early 2000s, country clubs hit an apex.
Golf was as popular as ever — in part because of Tiger Woods' mass appeal — and the economy was flourishing. New golfers took up the game like never before and country clubs, along with real estate developments around them, cropped up across the country.
But even before the economy started to sour, interest in golf began to wane.
After years of growth, more golf courses closed than opened in 2006, a trend that continued every year through 2014 at a ratio of more than 10 to 1, according to the National Golf Foundation.
The number of rounds played also went on a steady decline, falling to 462 million in 2013, the lowest mark in 18 years.
Once the economy started to decline, country clubs began to suffer. People had less disposable income or free time and country club memberships were an easy place to trim expenditures.
By 2012, 52 per cent of country clubs in the United States reported a loss in memberships, with just 22 per cent seeing a gain, according to a 2015 Sports Leisure Research Group report.
That left country clubs and developers caught in a bubble, needing capital to keep running the club and community, but no way to pay for it with initiation fees dropping.
"We got overbuilt, there were too many clubs built for how many golfers there were, then the golfers started to drop off," said Jim McLaughlin, senior vice-president of operations at Troon Prive, Troon Golf's private-club arm. "When you've lost 15-20 per cent of your market and growth still going on, that's when you get into trouble."
The economic downturn forced many country clubs to dramatically alter how they operated or face shutting down.
Clubs that were once invitation-only began opening their doors, drastically dropping initiation fees or eliminating them all together. Annual dues were slashed and some clubs even offered trial memberships with money-back guarantees.
Many country clubs were forced to offer reduced-rate tee times to the public just to stay afloat. Some became semiprivate, keeping members while allowing outside play, while others were forced to become fully public.
Country clubs also had to rethink fee structures.
For years, many clubs had an equity-based initiation fees, meaning members had to sell their memberships to leave the club. When the economy went south, members had a hard time selling their memberships; more people were trying to get out of country clubs than into them.
Some clubs offered a chance to downgrade memberships, become social or fitness members instead of paying full prices for golf memberships. That helped members to pay less per month, but made it nearly impossible to put a dent in their initiation fees.
To alleviate the glut, many clubs went to a market-based approach, allowing prospective members to put in offers to members, often at fractions of the original cost.
Troon Golf has 60 private clubs among its worldwide portfolio of about 200 golf courses and took nearly as many approaches to pulling country clubs through the tough times.
The core message for every club was the same, though: Stay true to who you are.
During the economic downturn, many country clubs tried to be everything to everyone, using a shotgun marketing approach to draw as many people in as possible.
Instead of bolstering the clubs, it often tore them apart, creating bickering factions within the walls instead of bonding like-minded members who had similar values.
"A club can have all these offerings, but the thing that's the heartbeat of it is the social experience in the middle," McLaughlin said. "I don't think that's going to ever change. We're Facebook for real. Community is important to everybody and being a part of something and feeling you belong, and that happens at clubs."
As the economy has started to recover, so have the country clubs that survived.
The rate of course closings hasn't waned — about 120-130 per year — but people have started returning to country clubs. In 2014, 39 per cent of country clubs gained new members while just 26 per cent had more members going out than coming in.
Winchester Country Club has started to bounce back after upgrading the clubhouse, the staff and the golf course, one of the last co-designed by Robert Trent Jones Sr. and his son, Robert Jr.
Winchester Country Club is up to 270 members after a low of 203. Initiation fees, once wiped out, are now up to $15,000.
"We've kind of got this momentum now where we've shown we can live up to what we said we were going to do," Bennett said.