When Ira Spiegel first came on to work as the accountant and financial advisor to embattled football star Michael Vick, it was a match made in bankruptcy court.

(Vick's not alone. Check out: Financial Fumbles: How the Economic Crisis Sacked 10 Pro Athletes)

From the beginning, the role had its challenges. Vick was in the midst of serving a 23-month jail sentence for his involvement in a dog-fighting scheme. That spiraled into other troubles, including Vick's suspension from the Atlanta Falcons and the loss of endorsement deals promoting brands like Nike. This was all while working with two financial advisors unqualified to handle his assets.

The result was a sharp decline in Vick's income — according to Chapter 11 bankruptcy filings — forcing him to rely on investments, savings and the sale of certain assets. As of September 2008, Vick's assets totaled $16 million, versus $20.4 million in liabilities, according to Spiegel.

Now, with Vick reportedly set to sign a franchise tag offer from the Philadelphia Eagles valued at an estimated $20 million for next season, the athlete is poised to come out of the Chapter 11 proceedings sooner than originally planned. "Should the [National Football League] play this season or, if not, the following season, Michael will — in an almost guaranteed situation — be able to pay 100 cents on the dollar to all of his creditors that have been approved as a creditor by the bankruptcy court, which is not the typical outcome in a Chapter 11," says Spiegel, a director of the bankruptcy and insolvency group at New York-based accounting and advisory firm EisnerAmper LLP.

But that same financial redemption is not always within reach for professional football players. Most NFL players, 78%, face bankruptcy or other financial stress as soon as two years after retirement, Sports Illustrated reported in 2009.

Those cautionary tales have played out in the press, most recently with former Chicago Bears defensive back Dave Duerson, who committed suicide in February amid ongoing personal bankruptcy proceedings and health concerns.

Combating that trend has sparked awareness efforts by groups like FINRA, the NFL and the Sports Financial Advisors Association, which have all ramped up their efforts to educate athletes. But permanently fixing that systemic problem may really come down to better connecting athletes with true financial professionals and, most of all, engendering trust.

When Spiegel first applied for the post as Vick's accountant and financial advisor, other firms were less than thrilled at the prospect of working with the athlete, Spiegel says. He was tapped to apply because of his relationship with Vick's legal team at Crowell & Moring LLP, but also because of his extensive bankruptcy experience that includes other athletes' personal Chapter 7 bankruptcy cases.

The final decision to appoint Spiegel to the case was made in September 2008 by U.S. Bankruptcy Judge Frank J. Santoro. That order states that for at least two years post-confirmation, neither Vick nor Spiegel can terminate the relationship without the judge's approval. "My being ordered by the judge to stay on as his financial advisor, not in a bankruptcy case capacity, but in the aftermath, was unusual for me, and from my understanding, [it was] a very, very rare situation to so order in any case," Spiegel says.

"The question of him learning about me, learning that he could trust me, learning that I'm working truly on his behalf — that took time," Spiegel says. "But that, I think, is standard in all new relationships and his was a little more strained because he didn't even have the chance to interview me and then hire me. It was kind of forced on him first by the attorneys and then the judge."

Part of the reason for that structure, Spiegel says, is the judge's reluctance to leave the decision in Vick's hands after the failures of his two previous financial advisor relationships.

Vick retained those two advisors after his 2007 indictment. The first was Mary Wong, a manager and investment advisor working with former Falcons teammate Demorrio Williams. Wong, a former Wells Fargo advisor who was working independently, was retained in the fall of 2007 and also had power of attorney.

She assumed that position after she had been barred from working with any firm that traded on the New York Stock Exchange. Vick ultimately sued Wong in a civil case for $2 million in compensatory damages, which was then turned over to a liquidating trustee. The case is pending. In a separate criminal action brought by federal prosecutors, Wong was sentenced in December to serve more than five years in prison and pay $3 million in restitution for a Ponzi investment scheme she operated from her Nebraska home.

In mid-2008, Vick moved to replace Wong with personal manager David Talbot. That decision was met with objections in Vick's bankruptcy proceedings. After Talbot was retained on an interim basis, Vick and his legal team learned he had several Chapter 13 bankruptcies and multiple judgments against him. In August 2008, Talbot's interim role and power of attorney were revoked completely when it was revealed that he and two other individuals had been charged with civil securities fraud for soliciting and spending money from members of a New Jersey church.

In a 2009 civil suit brought against them by the Department of Labor, Wong and Talbot and even Vick were permanently enjoined from serving as trustees, fiduciaries, advisors or administrators to any employee benefit plan.

Following those two previous advisors, Spiegel's biggest challenge in working with Vick was perhaps rebuilding trust, while preparing the star for a football comeback, and ultimately solvency. The two began their professional relationship in court. And while Vick was in jail, contact was limited to weekly attorney meetings and mail and fax correspondence. Now, that relationship has expanded to regular contact by phone, email and in person. "Michael and I obviously had to learn to know each other," Spiegel says. "Just like in any relationship, there were bumps in the road, but I think we've reached a very, very comfortable working situation at this point. A couple of times we've had discussions, the implication was that he doesn't look to end our relationship in the near future, if at all."

The plan laid out in court calls for a six-year payout window, which started in 2009 when the liquidation trustee was elected. Vick chose to stay in Chapter 11 bankruptcy versus Chapter 7 bankruptcy liquidation because he wanted to do right by his creditors, Spiegel says. That decision put a burden on Vick to sell assets, leaving him with just one home for his family, down from at least four houses and condominiums listed in his bankruptcy filing.

Even with more than $5 million in earnings last year, Vick must stay on the established budget with a fixed living expense allowance, Spiegel says. Regular payments are made to his creditors and a trustee handles payments to unsecured creditors. Quarterly operating reports are also sent to the U.S. Trustee's office.

The goal for the existing budget is to preserve Vick's money, says Spiegel. That mean little or no risk for now. Spiegel has set up escrow accounts, using CDs or money markets with interest, to set money aside for payments and savings. From there, they will likely move toward low risk investments like bonds, with the goal that Vick will have funds set aside for his future post-bankruptcy.

Vick will likely repay his creditors before the six-year time frame for the plan has passed, Spiegel says, as his new reportedly $20 million tender sheet exceeds the estimated $5 million per season on which the plan was based. That tender sheet will become a contract, provided the NFL bargaining agreement comes through. Once Vick has paid the bankruptcy debts, the judge will likely issue a final decree and close the bankruptcy case.

"The process is being sped up by [Vick's] performance on the field and earning that franchise tag," Spiegel says, noting that the next goal is to make sure he is prepared for retirement. "There will be significant monies set aside in the savings escrow to protect Michael toward the end of his career, which we all anticipate will exceed the six years of the bankruptcy plan. [It will] at least give him comfort that when we've finished our primary job, he's already got something [for the] future."

Vick's return as a successful quarterback is only part of the story, says Michael Blumenthal, a partner at law firm Crowell & Moring. "He is now a functioning person back in society. He is doing great, not just financially, but as a person."

While Vick's career downfall and comeback has been well documented in the press, many other football players face the same financial afflictions-without the accompanying attention. That trend led FINRA to team up with the NFL to bring financial education to prospective professional players at two college bowl games in January: the East/West Shrine Game in Orlando, Fla., and the Under Armour Senior Bowl in Mobile, Ala. At those events, the groups delivered 60-minute presentations and hosted information booths.

The challenge is to make players understand that they are targets and susceptible to fraud, said John Gannon, senior vice president for investor education at FINRA. That begins before players join the professional ranks, he said, which is why the NFL and FINRA aimed to reach the athletes at college events. "We originally developed this program for older investors because they are targeted by investment fraud," Gannon says. "What is the commonality between NFL players and older investors? They both have a lot of money."

The persuasion tactics for both groups are also the same, Gannon says. That includes promises of phantom riches, or impossibly quick, guaranteed returns; social consensus, or investing because someone else has; reciprocity, doing business with someone after they provide you with a gift or a meal; and scarcity, with a limited amount of the investment available. FINRA also educates investors to beware of solicitors who may fake credibility with fancy clothes or cars.

Working with a financial professional after being approached or hearing about them through word-of-mouth is okay, Gannon says, as long as they take steps beyond that to check the situation out. That includes checking to see if that individual is a licensed financial professional or that the investments they're selling are registered securities products; if they have disciplinary actions against them; or any additional information they can garner about an individual or firm. "A coach will tell somebody about a financial professional investment. So 'if coach likes it, it has to be okay,'" says Gannon, giving a hypothetical example. "People will not necessarily do their due diligence in a situation where they see people, similarly situated to themselves, already invested. It may be that no one has done their homework."

The NFL's work with FINRA is just part of its efforts to educate its athletes that first began in the 1980s, according to Adolpho Birch, NFL senior vice president of labor policy and player development. Its services can range from helping to run a background check on a financial advisor, to career coaching, including intern placement and interview training for players at the end of their careers.

Ultimately, it is up to the athlete to make shrewd money management decisions and understand the value of the NFL brand. This, Birch says, can lead to opportunities that might otherwise not be available. Many former NFL players have gone on to even more successful second careers. "We've got countless players who have gone on from what would be considered minor NFL experiences, to own businesses or are involved in a number of opportunities and lead successful lives-some of them more so than when they played," Birch says.

For the professional financial advisor looking to build up the business with athlete clients, one of the greatest challenges can be first connecting with them, says Andre Mirkine, president of the Sports Financial Advisors Association. Once they become clients, the next challenge is educating them and making sure they stay in line with the financial goals set out for them.

Mirkine, a financial advisor with Wells Fargo Advisors in Old Greenwich, Conn., has gathered a select group of athlete clients through referrals. They include basketball players, baseball players and alpine skiers, a sport that he used to compete in professionally. But, he says, his desire to work with athletes does not mean he has always said yes to every prospective client.

"I try very hard to get them to save a measurable percentage of their salary," Mirkine says. "If it's not significant enough and I see a situation where they're just going to burn through their money, it's not going to work for me."

Mirkine turned down a prospective client recently, he says, when a professional basketball player seeking lending services for a third home, was referred to him. That athlete, who is not an investment client, had a poor financial profile after 10 years in the National Basketball Association. That included a low credit score and a positive net worth, only because the value of his jewelry and automobiles exceeded the amount he owed on them. With just a couple of years left on his contract, Mirkine declined to provide a loan to that athlete and offered to help him address his more pressing financial issues. Mirkine did not hear back from that athlete.

Football players face the same financial challenges, especially now with the uncertain contract disputes the NFL is currently wrangling through, Mirkine says. If a player has not been properly saving, financial difficulty could set in as soon as the paychecks stop.

To prevent that kind of financial crunch, Brendan Biruk, a financial advisor at UBS Financial Services' BR Group in Newtown, Pa., works harder with athlete clients to educate them, keep lines of communication open, and build cohesive teams that include their wives, tax accountants and attorneys.

"We want an athlete to call us before they make any purchase," says Biruk, who is also a member of the SFAA. "Anything they do that relates to their investments, earnings or finance, at least bounce it off us first for a financial perspective. Whether it's a car, house or whatever, [we] make sure it's suitable and do it in the proper structure."

In order to truly reach athletes, Mirkine says, educators need to scale their efforts so that they can visit 150 schools more than once every three years. The key, Mirkine says, is to reach athletes before it is too late. "It's like a kid in a candy store. It's a culture that they've aspired to-they see all over T.V., and in magazines," Mirkine says. "Once they've been elevated to that lifestyle, or the ability to have that lifestyle, it's very difficult to talk to a professional athlete and convince them they should save a measurable percentage of their income."

As for Spiegel, it's still not certain whether Vick will remain with him once he is clear of bankruptcy. However, Spiegel says, "I would like to hope that our relationship continues and that-obviously once all the restraints put on by the bankruptcy are removed-we can then look to the entire EisnerAmper firm to give him support in potential investment opportunities and management of the money."

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