In August 1998, New York real estate financier Andrew Penson made the first offer for the Redskins and Jack Kent Cooke Stadium before the bidding for the assets officially opened. With backing from Lehman Brothers, the 37-year-old Penson offered $450 million, which would’ve been the highest amount paid for an NFL franchise. It would turn out to be barely half of the eventual winning bid.

“Bethesda Man To Make Bid For Redskins,” read the headline in The Washington Post on Nov. 7, 1998, the first mention of Snyder’s interest in purchasing the football team he grew up following. The Post reported that the “33-year-old businessman who heads a Bethesda-based communications empire” would join the bidding after receiving one of the initial offering memorandums distributed to potential buyers by Morgan Stanley Dean Witter.

Eleven years earlier, Snyder founded Snyder Communications Inc. with his older sister, Michele. The marketing services company grew from $43 million in revenue in 1995 to $333 million in revenue in 1997, and Snyder, who took marketing classes at Maryland, in 1996 became the youngest person to head a company listed on the New York Stock Exchange.

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John Kent Cooke, The Post reported, told friends he would bid whatever it took to keep the Redskins in the family, where, he said, “it belongs.” The competition would be stiff. Two weeks before a Nov. 23 deadline for initial bids, as many as 10 bidders had submitted offers. They included Baltimore Orioles majority owner Peter Angelos, Arizona hotelier Sam Grossman, Fort Worth investor David Bonderman, shipbuilder and New Jersey Devils owner John J. McMullen and New York real estate investor Howard Milstein. Grossman’s group included former Redskins Coach Joe Gibbs, while Bonderman partnered with Washington real estate developer and future Nationals owner Ted Lerner. Experts predicted the sale would fetch at least $500 million.

“Potential buyers see dollar signs and the tradition of one of the NFL’s great franchises,” Chris Dunlavey of the D.C. firm Brailsford & Dunlavey told The Post. “Their stadium is a cash machine."

A few days before initial bids were due, Snyder formed an alliance with Milstein, who, along with his brother, Edward, owned 45 percent of the NHL’s Islanders. The six trustees tasked with reviewing the bids were expected to make a decision by Christmas, after which a three-fourths majority of NFL owners would be required to approve the transfer of ownership.

Eight groups were invited to submit a second round of bids due Dec. 22. Milstein and Snyder attempted to preempt the process and pressure the trustees into making a quick decision by offering more than $700 million in cash, with the stipulation that the offer would expire one day after the rest of the bids were due. Their early bid was declined, but Milstein and Snyder remained in the running, and on Jan. 10, 1999, the duo signed an agreement to buy the Redskins for approximately $800 million.

“I had the desire and the will — even the ingenuity — but not enough money to keep the Redskins in my family,” Cooke, whose bid approached $700 million, said in a statement.

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The sale still required approval by the NFL’s owners. With the Redskins’ ownership in limbo, the team’s negotiations with free agent quarterback Trent Green stalled. Green ultimately rejected a four-year, $12 million offer from the Redskins and signed with the Rams.

The NFL had made it clear it would’ve preferred the Redskins remain with the Cooke family, which won three Super Bowls in 25 years of majority ownership. League officials informed the trustees they would waive several financial requirements for John Kent Cooke, including a minimum amount of personal wealth required above the money included in his bid. The league wouldn’t make similar concessions for other groups.

The league spent much of the next two months scrutinizing the Milstein-Snyder offer. In mid-February, the NFL’s finance committee requested more financial documentation from the group and hired a private investigator to do background checks on both men. In early March, NFL officials asked Milstein to restructure the $400 million loan that was at the heart of the potential deal. Why the hold up? In addition to concerns that Milstein’s financing plan was too debt-laden, there were reports that some NFL owners worried Milstein was too litigious.

At a March 17 meeting in Phoenix, NFL Commissioner Paul Tagliabue granted a request by Milstein and Snyder to delay the vote on their purchase of the team, saying “there’s a feeling on both sides it’s been a media event when it should be a business process.”

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“We’re in overtime now,” Milstein said after Tagliabue’s announcement. “We finished the regulation period. We will fully satisfy the NFL. The fact we’re still standing here and going to overtime means we’re going to do it.”

“This is like a marriage and before you get into any marriage, you have to be careful,” Tampa Bay Buccaneers owner Malcolm Glazer said.

Ahead of a special owners’ meeting to vote on the sale on April 7 in Atlanta, Milstein received $125 million in cash from his father, Paul. Some owners considered it a loan and remained concerned that much of Milstein’s bid was secured by real estate holdings. Milstein and Snyder withdrew their offer when it became clear they still didn’t have the required support for approval.

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Snyder began working to secure financing to match the group’s $800 million offer without Milstein’s support. His revised bid was backed by family members, as well as Mortimer Zuckerman and Fred Drasner, original investors in Snyder Communication, and included $350 million in equity. Cooke upped his offer to $720 million, but withdrew it in late April when it became clear Snyder and the trustees were nearing a deal.

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“I refuse to be used merely to increase the bids of others, since it is well known that I have always wanted to keep the Redskins in my family,” Cooke said.

Grossman also reentered the bidding with the support of FedEx founder and chairman Fred Smith, but withdrew his roughly $800 million offer shortly after Cooke bowed out.

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“We felt that the trustees may be legally obligated to [Snyder]," Grossman said. “If the opportunity arises and the Snyder group is rejected for any reason, we will reenter.”

On May 25, 1999, NFL owners voted unanimously to approve the sale to Snyder’s group, breaking the record for an NFL franchise deal by more than $250 million.

“I’m not focused on the money, I’m focused on the opportunity and the dream,” Snyder said. “Hundreds of fans have written to me with their support and suggestions . . . Your most pressing issue is no different than mine. You want to win, we want to win, and we’re going to deliver that.”

While Snyder no longer had a financial relationship with Milstein, he said during the news conference announcing the sale that he still considered him a friend. A week earlier, Milstein filed a federal lawsuit in D.C. against John Kent Cooke and Redskins General Manager Charley Casserly, alleging the duo conspired with NFL officials to undermine his bid to buy the team. The suit was thrown out.

Snyder praised the Cooke family’s stewardship of the Redskins franchise and vowed to uphold the legacy the family had created. John Kent Cooke was understandably disappointed.

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“The executors and their representatives stated that accepting the highest bid was their fiduciary obligation, required to fulfill my father’s wishes and comply with the law,” he wrote in a statement. “None of these claims is correct, and the result of this decision is the loss of a family business and a personal tragedy to me . . . I am consoled by my memories of the many great years that my family has been associated with the Redskins and the NFL. I wish all the Redskins fans many Super Bowls. Hail and farewell!”

While Snyder began to leave his mark on the Redskins, Cooke, who netted about $60 million in the sale, joined the board of his father’s foundation, which was established in 2000 and has awarded more than $190 million in scholarships. In 2017, Cooke, who also owns Boxwood Winery in Middleburg, told former Post reporter Leonard Shapiro he thought one of the reasons the trustees agreed to sell the team to Snyder was that they feared a lawsuit.

“I do believe that if I had retained the Redskins, the foundation still could have been born and would have been as world famous as the Redskins were,” he said. “Both things could have been accomplished . . . In my opinion, the sale was totally botched.”

Twenty years, eight head coaches and two playoff wins since Snyder took control of the Redskins, it’s hard not to wonder how things might have turned out differently for the franchise had another bidder emerged victorious.