"It was," he says, "paralyzing, debilitating."
Gerut, 35, shakes his head when he looks back at that old portfolio and his own ignorance. Had he not wised up early in his big league career, done his homework and started managing his own money, who knows how much that particular portfolio would have crippled his post-playing funds?
During parts of six seasons, Gerut was an American League Rookie of the Year candidate with the Indians in 2003 and a Comeback Player of the Year candidate with the Padres in 2008. In between and afterward were assorted knee problems, platoon roles, Minor League assignments and bench jobs that kept his career from being particularly lengthy or celebrated.
Gerut, though, was an undeniably interesting player -- probably one of the few who subscribed to The Economist or immersed himself in textbook-sized biographies of political greats. His answers in interviews were always just a little more thoughtful, a little more insightful, and, yes, a little more wordy. When he announced his retirement in early 2011, he did so with a 231-word statement that was refreshingly honest.
Baseball-Reference.com estimates that Gerut made just north of $5 million in his career, plus the $450,000 he received as a signing bonus after the Rockies drafted him in the second round in 1998. Over time, he learned to spend and invest his money wisely, and so today he lives quite comfortably.
But Gerut's story is no longer about his own money. His focus these days, in his newly embraced role as a player agent for Wasserman Media Group, is on other people's money. It's on the remarkable number of professional athletes who don't wise up, don't take care of their future savings while racking up their current earnings.
Maybe it's a difficult topic for average fans to understand or even sympathize with, especially at a time of year when we're routinely hearing about Major League ballplayers signing contracts worth unbelievable amounts of money. But the number of pro athletes who go broke is staggering.
A few years back, Sports Illustrated culled sources -- including athletes, players' associations, agents and financial advisers -- and found that 78 percent of former NFL players had gone bankrupt or were under financial stress within two years of retirement and 60 percent of NBA players were broke within five years of retirement.
The magazine did not report a percentage for MLB, where the bankruptcy issue is not nearly as pandemic, but it did mention ballplayers like Johnny Damon, Jacoby Ellsbury, Mike Pelfrey and Scott Eyre getting tied up in Texas financier Allen Stanford's $8 billion Ponzi scheme.
Truth is, the majority of us don't know much about money or how to save or invest it. The majority of us also don't make the kind of money that professional athletes do. For them, poor decisions can be crippling, not just because of the sheer amount of money involved but also because of their relatively brief peak-earnings potential.
That was something Gerut picked up on early in his Major League career. He's thankful he did. By the end of his career, which included stints as a union representative, coaches and teammates would approach him for advice about their personal finances.
"I got a chance," he says, "to see some of the crap that was being brought to players."
Shaky real-estate deals. Investments in bogus inventions. Family friends looking for handouts. You name it, and the millionaire athlete sees it. And it can become all too easy to throw good money at bad.
After his retirement, Gerut started to dig deeper into the issue. For one, he studied for and received his investment adviser license from the Securities and Exchange Commission. He also spent six months researching athlete bankruptcy in the four major professional sports, talking at length with agents, players and advisers.
He found that, in MLB in particular, the bankruptcy rate for foreign-born Latino players was significantly higher than that of other ballplayers. He estimates that 70 percent of foreign-born Latino players in MLB endure financial hardship within four years of retirement.
"In a lot of cases, there's a lot of trust being put into people that shouldn't be trusted," Gerut says. "There's a lack of understanding of what power of attorney means and the implications of giving the wrong person power of attorney.
"If there's one consistency through my interviewing with bankrupt or financially distressed guys, it was, 'I couldn't say no to family.' So you've got some really difficult human situations, compassion situations."
Gerut's compassion for this particular issue led him to an industry that, fairly or not, is not always known for compassion. He never set out to become an agent; in fact, his goal was to start a consulting firm. But he quickly discovered that the best way to work with players was to represent them, and he joined Wasserman last fall.
"My life's work," he says, "has become the reduction of athlete bankruptcy down to zero percent. As much as I want to be an agent that pushes the market appropriately, I also want my identity to be the anti-bankruptcy agent."
His goal is to better educate today's athletes, particularly those in Latin America, about life after sports, and this means educating himself as well. He's considering a position on an advisory board for a nonprofit dealing with athlete bankruptcy, and he's also studying up on franchising -- a popular investment for current and former athletes -- so that he'll be able to provide proper counsel to clients considering that course.
Just as Gerut was an atypical Major Leaguer, he is now an atypical agent -- one invested as much in a player's post-playing security as his current earning potential.
Gerut is early in his new career, but it could be an interesting one to follow, focused as it is on an oft-overlooked issue in American sports.