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The Lesser of Two Weasels?

As we lament the many plagues of the Dan Snyder era, consider this: Howard Milstein could own the Redskins.

Last week, the law firm of Boies, Schiller & Flexner—the workplace of David Boies—took a break from litigation on behalf of what sources describe as “a candidate for the most powerful office in the world” to try to resuscitate another of the superstar attorney’s cases, this one in representation of Milstein. The firm filed a motion with a federal appeals court in Virginia hoping to overturn a host of lower-court verdicts that went against Milstein, all related to his client’s attempted acquisition of the Skins. Boies, rather like the team, finds himself on something of a losing streak.

Milstein had sued John Kent Cooke and other officials with the estate of former Redskins owner Jack Kent Cooke (including former Skins general manager Charley Casserly) for their conduct during the thwarted sale of the team to Washington Sports Ventures, a group Milstein headed. The scion of one of New York’s wealthiest families contended that, but for the actions of John Kent Cooke, the scion of one of Middleburg’s wealthiest families, he would now be spending his fall Sundays in the owner’s box at Milstein Manor—or whatever he would have renamed the Redskins’ home stadium.

As we now know, Milstein never got that chance. To recap: The Redskins were put up for bid by the estate of Jack Kent Cooke not long after his death, in April 1997. Milstein won that auction in January 1999, against bidders including John Kent Cooke, by offering $800 million. But even though Milstein’s bid, still a record sum for a sports franchise, was accepted by the estate, the NFL owners eventually pooh-poohed it. Those same owners allowed the platform-shoed Snyder, originally a junior partner in the Milstein group, to match the big bid and take over the Redskins.

Among the reported reasons for Milstein’s rejection was that many in the NFL brotherhood thought he would be too litigious. Milstein denounced that charge, even after his bid to get the Skins was so brutally rejected, and some bought into his denunciation. On Thursday, April 29, 1999, the Washington Times reported: “Howard Milstein’s hiring of top litigator David Boies is not expected to result in a lawsuit against the estate of Jack Kent Cooke.” The paper cited “sources close to the sale and legal experts.”

Oh, well. Three weeks after the Times report, Milstein filed against John Kent Cooke et al. In the suit, Milstein contended that Cooke, hoping to keep the team in the family, had instigated the whupping Milstein took from NFL owners and that Cooke’s attempts to gain control of the team even after bidding less than Milstein were in violation of his duty as a trustee of the estate to get the most money for his dad’s holdings. Jack Kent Cooke’s will called for all proceeds from the sale of his stuff to go toward a charitable trust.

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“Mr. Cooke acted against approval of the sale of the team to the Milstein group and instructed Mr. Casserly to do the same,” says Jonathan Schiller, a D.C.-based partner of Boies’. “He told other owners he still wanted the team. When Mr. Casserly went to a meeting of the owners, he expressed Mr. Cooke’s disappointment and was critical of the Milstein group. As the agent of Mr. Cooke and the team, it was his obligation to make sure he was supportive of the approval. He didn’t do that.”

Despite the appeal, Milstein’s suit now seems about as dead as Gore’s transition plans. In late October, a judge in U.S. District Court threw out the last of five counts of Milstein’s complaint against Cooke and his partners. The federal court even said that the estate didn’t have to refund the $20 million Milstein had put down as a deposit to buy the team.

Because of national media portrayals, Boies came into the Gore litigation with an aura of invincibility. Much of that rep was deserved: He did bring Microsoft to its knees, fer chrissakes.

But the Redskins litigation proves that Boies is beatable. Just ask David Donovan, the D.C. lawyer who, as Cooke’s attorney, played David to Boies’ Goliath.

“If you lose five out of five counts, that’s a loss,” says Donovan. “David Boies has got to count this as a loss….But you could say this was a good-lawyer, bad-case situation.” (Milstein has another odd connection to the 2000 presidential campaign: His first cousin Connie Milstein is the woman who allegedly gave cigarettes to about a dozen homeless Milwaukeeans in exchange for Gore votes.)

Milstein’s résumé shows that, unlike Boies, he hasn’t won much. In 1994, Milstein was involved in a failed effort to found the United Baseball League, a confederation proponents hoped would one day rival Major League Baseball. In 1995, he was part of the group behind Major League Football, a proposed rival to the National Football League that never kicked off.

He makes enemies easily. In 1998, while Milstein was trying to buy in to the Toronto Blue Jays, his relationship with reporters north of the border went south almost from the outset; one Toronto columnist wrote that if Milstein were approved as the Jays’ owner, he’d bring a “Bulldozer Durham” ethic to the national pastime. The team looked elsewhere for financing.

An attempt by Milstein to bring an NFL franchise to Canada also died, as did a plan to build what was billed as a $140 million shopping center and casino operation near Niagara Falls. Milstein’s Cleveland Sports Ventures, though a finalist in the bidding for the Cleveland Browns expansion franchise, lost out to a group led by Al Lerner. Then Milstein tried to buy the NBA’s New Jersey Nets but was turned down.

Milstein finally got himself a sports franchise in 1998, when his New York Sports Ventures paid $195 million for the New York Islanders, a record sum for an NHL team. Milstein’s stewardship of the once-storied franchise was an unmitigated disaster, with fans and players abandoning the squad after accusations that he had bought the team only in order to develop the land around its decrepit home arena, Nassau Coliseum. Milstein also shipped off all the Islanders’ stars, reduced the payroll to a league-low $15 million, and, at one point, threatened to move the team to Cleveland. What was left of the Islanders’ following cheered when he sold the team last year to Charles Wang at a loss.

And, earlier this year, Milstein found himself on the business end of a lawsuit filed by members of his own family. Among the allegations: He had used family money to finance his sporting ventures without getting proper permission.

But not everybody thinks of Milstein as a bad actor.

“Mr. Milstein has been wonderful to us,” says Veronica Park, president of Martha’s Table. Last year, long after he’d been rejected as Skins owner, Milstein donated $25,000 to the D.C. soup kitchen. The money helped finance an expansion of the preschool area inside the organization’s 14th Street compound. Milstein asked for nothing in return for the donation, which got no publicity either here or in New York. —Dave McKenna