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As Pamela Gaskill walked through San Francisco's blighted Tenderloin district one day in 2000, she had an epiphany.

Observing impoverished residents of single-room-occupancy hotels, she realized she had no financial resources for her own retirement. Gaskill, a slender, weathered woman who has driven trucks since the late 1970s, thought, “This is what happens if you don’t have a pension. People end up in a tiny little room with nothing.”

Unlike other full-time workers enrolled in traditional pension plans or even 401(k)s, Gaskill, who drives a 65-foot 18-wheeler for Oakland, California–based Rock Transport, received no benefits in her years as an independent trucker. After she joined Rock Transport in 1989, she tried unsuccessfully to negotiate benefits. Then Gaskill and her partner, Dennis Holocher, another Rock driver, decided to push for union representation — a daunting task. “The drivers were scared,” she recalls. “They thought if we went union, the company would fold or let us go.” In 2002, after a year of organizing, Rock Transport employees joined the Western Conference of Teamsters. Best of all, they also became members of the union’s pension fund.

Having a retirement benefit changed the way Gaskill viewed her work. “I called my dad so he’d be proud of me because now I had a real job,” she says. Gaskill succeeded Holocher as shop steward after he retired.

Gaskill and Holocher were lucky. They are among the nearly 583,000 participants in the largest multiemployer defined benefit plan in the U.S., the Western Conference of Teamsters Pension Trust. The WCTPT is the best funded of 194 pension funds jointly sponsored by employers and local or regional units of the International Brotherhood of Teamsters. “They’ve been conservative in their investments, professional in their management and fortunate in their economics,” says Joshua Gotbaum, director of the Pension Benefit Guaranty Corp. (PBGC), the federal agency that insures both single and multiemployer pension funds.

Today the WCTPT is a $35 billion fund that receives contributions from more than 1,400 employers, ranging from small companies with fewer than 50 workers to major corporations like Coca-Cola Co., Safeway supermarkets and United Parcel Service of America.

Although the American labor movement dates to the late 19th century, the creation of pension funds for union members took more than 50 years. The multiemployer pension plan was designed to allow union workers — truck drivers, vegetable packers, floor sweepers, construction workers — to build retirement nest eggs despite frequent job changes. Founded in 1955 as a multiemployer plan for Teamster members in 13 western states, the Western Conference pension plan, like many others, was fully funded for decades. Then a series of legislative initiatives, including trucking deregulation and the Multiemployer Pension Plan Amendments Act, both passed in 1980, as well as demographic and technological change, put many trucking companies out of business. As union shops disappeared, the number of active union members fell. And two financial crises in a decade blew a hole in the idea that multiemployer funds could continue to operate as they always had.

Thanks to careful fund oversight and a diversified membership, the WCTPT was able to fend off some of these blows. But even the strongest pension fund could not remain untouched by market breakdowns like the dot-com bust and the 2008–’09 crisis. As a result, WCTPT trustees, shocked by successive multibillion-dollar losses, decided to break their long silence and add the fund’s voice to efforts to fix a struggling system for 10.4 million union members.

For a long time, says Charles Storke, the WCTPT’s lead attorney and a partner at San Francisco law firm Trucker Huss, the attitude of Western Conference officials was “We should tend to our own knitting without regard to what else is going on in the world.” Michael Sander, the fund’s administrative manager and a partner at Seattle-based Northwest Administrators, agrees: “We’ve been dark for so long, there’s nothing you’re going to find if you google us. Circumstances have changed, and we need to carry the banner.”

But can the WCTPT save itself and the union’s multiemployer pension model? It won’t be easy. Multiemployer plans face problems deeply rooted in the decline of American labor unions in a global, postindustrial world. The unions, after all, still offer traditional defined benefit plans, which many employers have dropped in favor of less expensive, less risky defined contribution plans. The market outlook remains deeply uncertain, demanding sophisticated investing skills. And the politics of saving multiemployer pensions, particularly in a bitterly divided Congress, are problematic at best.

THE WCTPT WAS THE CREATION OF TWO CONTROVERSIAL veteran union figures: Frank Brewster, head of the Western Conference of Teamsters from 1953 to 1957, and David Beck, who served as president of the national Teamsters organization from 1952 to 1957, when he was replaced by a tough guy from Detroit named Jimmy Hoffa. Brewster, who in the 1940s conceived of the Western Conference as the first Teamster region, teamed up with Beck to start a comprehensive pension trust with the idea that Social Security alone wouldn’t provide sufficient income for retirees.

But Brewster and Beck, who helped modernize the Teamsters union, which received its national charter in 1899 from the American Federation of Labor as a national organization, got caught up in the mid-1950s federal racketeering probes. Although neither was found to have Mafia connections, both were charged with unrelated crimes after being hauled before the Senate’s Select Committee on Improper Practices in the Labor or Management Field, dubbed the McClellan Committee after senator John McClellan. Both received prison sentences. Brewster’s conviction for contempt of Congress for refusing to testify was overturned on appeal. In 1975 president Gerald Ford pardoned Beck, convicted of embezzlement and tax fraud.

Though the two founders created a legacy of retirement benefits for union workers, they left a black mark on the WCTPT in its infancy. Despite the fact that the fund was found free of scandal by the McClellan Committee — and later by David Witwer, a history professor at Penn State Harrisburg and author of Corruption and Reform in the Teamsters Union — fund officials retreated from dealing with the outside world.

As the WCTPT fund grew, its trustees made decisions that kept the plan well funded. In the 1980s they created a formal funding process with a flexible benefit-accrual formula that allowed them to make adjustments as economic conditions shifted. In the bull market of the late 1990s, the WCTPT set benefits at a peak of 3.65 percent times dollars contributed. After the dot-com bust, trustees dropped accruals to 1.2 percent. An optimistic adjustment brought the number back to 2 percent just before the financial crisis. “In good times we can improve benefits, and in bad we tighten our belts,” administrative manager Sander explains.

Bad times meant that on January 1, 2009, trustees again took the accrual rate down to 1.2 percent, where it remains today. “It’s better to keep a steady accrual rate and the plan funded strongly,” Sander says. After the crisis the WCTPT used the fund’s size to negotiate lower asset management fees. “The smart managers were clever in how they restructured their fees,” says Sander bluntly. “The dumb managers did not. And some are no longer with us.”

Even at the height of the 1990s bull market, employers never took a contribution holiday, which was common at that time. The Western Conference’s early decision, led by Beck, to diversify membership rather than build locals solely with truck drivers also helped. Today about 45 percent of members do not drive trucks.“One of the reasons the plan has been strong is we have flexibility to put a variety of employers and employees in it,” says longtime Teamster leader Charles (Chuck) Mack, a co-head of the WCTPT. “We’ve never taken the position ‘We don’t want these people in our plan.’” Truck drivers, food processors, office workers and public employees all negotiate their own benefits and are bound by individual collective bargaining agreements with their employers. “The economic circumstances for a food-processing plant wouldn’t be the same as UPS, which is more militant and stronger,” Mack says.

Perhaps most important, the WCTPT early on took precautions to keep assets away from the Teamsters and organized crime, which in the 1950s and ’60s looted assets from the Teamster’s Central States Southeast and Southwest Areas Health and Welfare Fund to finance casinos. The trustees initially moved nearly all their assets to Newark, New Jersey–based Prudential Financial to invest in fixed income, real estate and annuities. There they stayed until the early 1980s, when the trustees decided to venture into other asset classes.

After searching for an investment consultant to help with asset diversification, they selected Alan Biller, founder of fiduciary consulting firm Alan Biller and Associates in Menlo Park, California, in 1986. (Biller likes to say he started his company in his garage in 1982.) At that time, 84 percent of the portfolio was in dedicated bonds. “In the early 1980s you could buy long bonds with yields of 12.5 to 14.5 percent,” Biller recalls. For years the WCTPT restrained Biller from straying from traditional stock and bond portfolios. In 1987 he proposed investing in farmland, but the trustees decided that was too unusual. “We discussed it in 1987 and invested in 2011,” he jokes. In the early ’90s he got approval to build an enhanced equity index portfolio. “We were making what we needed, so they didn’t need to do much else,” he says.

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