Behind the scenes of how Tiger Woods' Upper Deck deal came together

Golfer's landmark agreement paid for itself in one day, produced Woods' iconic rookie card

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Upper Deck convinced Beckett to classify Tiger Woods' 2001 Upper Deck card as his true rookie. (Credit: Getty Images)

Upper Deck paid $15 million over five years to sign Tiger Woods in 2000.

The company knew Woods' rookie cards were going to be the cash cow, with later years providing only a fraction of the opportunity, so it really only had one year to recoup that investment.

And Upper Deck did so … on day one — to the tune of 58,000 cases sold on the first day of the launch of the 2001 Golf set, accounting for around $20 to $25 million in revenue.

What has now turned into a classic set for collectors around the world, with signed Woods rookie cards from the set reaching as high as $336,000, was an undertaking that bears little resemblance to the yearly releases churned out for most other sports.

It was about courting the biggest athlete in the world and building a product around him first and foremost. And it proved to be one of the most successful card releases in history as the company recouped its investment in the first 24 hours of the launch.

Woods was easily the most marketable athlete in the world in the early 2000s. (Credit: Getty Images)
Woods was easily the most marketable athlete in the world in the early 2000s. (Credit: Getty Images)

Catching Tiger

By the turn of the century, Woods had firmly planted his flag as the most dominant athlete on the planet.

After turning pro in 1996 at age 20, Woods rattled off a series of record-breaking accolades that turned the sporting world on its head. The youngest-ever Masters winner in 1997, the quickest rise to No. 1 in the world and a 1999 season which culminated in a PGA Championship.

He was arguably the most marketable human on the face of the earth, and his checkbook reflected it: Multi-year deals with Nike and Titleist promised him $60 million before his first professional victory. By 2000, in a Nike stockholder meeting, after Phil Knight upped the rate to $20 million per year over five years, the company president was asked if there was a better way for Nike to spend $100 million.

The answer was a simple “no.”

For those early years, Woods’s deals with those core sponsors remained his focus, despite brands from every plausible category scratching and clawing their way into his eye line.

One of those companies was Upper Deck, which already boasted deals with Michael Jordan and Wayne Gretzky.

“We were calling him immediately in 1996 at Upper Deck Authenticated, and he wouldn’t even talk,” said Bill Dully, Upper Deck president and chief operating officer from 1993-2003.

As Woods' business dealings evolved, growing into a sophisticated ecosystem of representatives, agents, lawyers and go-betweens — all culminating with the golfer and his agent Mark Steinberg — Upper Deck was finally able to get its name in the running in mid-1999.

It took more than six months (as opposed to the six weeks typical of negotiations at the time) of escalating meetings and negotiations, but eventually, the team at Upper Deck was able to reach Tiger for the final decision, who took the meeting in a hotel conference room in Los Alamitos, California, along with his parents.

“Tiger is probably the most involved athlete I ever worked with in his own affairs,” Dully said.

Woods walked in with four McDonald’s bags full of a dozen quarter-pounders and three large fries.

As part of the pitch, the team showed Woods a piece of technology in the works utilizing fingerprints to authenticate autographs. Mike Gardner, Upper Deck’s senior vice president of sales and marketing from 1993 to 2004, remembers Woods testing it out on a program, which he signed “Jack Daniels.”

“I'm gonna get that thing. What a cool collectible that's gonna be for me to grab, Gardner recalled thinking at the time. “So everybody's shaking hands and I go to the table and I start to pick it up. He puts his hand on it, and says, ‘You can't have that’.”

Woods was acutely aware of the value, both financially and culturally, of his signature. Even if it had the name of a whiskey brand on it.

Woods' agent Mark Steinberg played a key role in bringing the deal together with the PGA Tour. (Credit: Getty Images)
Woods' agent Mark Steinberg played a key role in bringing the deal together with the PGA Tour. (Credit: Getty Images)

'It was like birthing a calf'

The deal would guarantee Woods $3 million per year for five years, as well as 13 percent royalties, for 7,000 autographs per year and the rights to include the phenom on exclusive memorabilia and trading cards. No personal appearances were required, no advertising and no rights to image or likeness beyond the specified cards and memorabilia.

For reference, Upper Deck’s deal with Jordan, signed years prior, paid him $1.2 million per year and required 8,000 autographs. Jordan received a 21 percent royalty, whereas Woods requested a higher guarantee.

Upper Deck created a full suite of offerings surrounding Woods, including co-branded products with Woods sponsor Nike, creating limited-edition golf balls with his autograph. Prior to the deal, Woods refused to sign golf balls for anyone other than friends and family. Not only were they hard to sign, but he was extremely wary of fraudulent autographs hitting the market — a concern that partially incentivized Woods to go with Upper Deck and create a source for his authentic memorabilia.

One of the hallmarks of Upper Deck during that era was its technology, like its holograms applied to signed items signaling authenticity and discouraging forgeries.

Though it very well could have been enough to simply push out a set of cards with only Woods’ face on them, Upper Deck’s work was cut out to deliver on the promise the most substantial licensed golf trading card set in years. One which would be anchored by Woods’ rookie card, but also feature greats of the past such as Arnold Palmer and fellow PGA Tour players with less name recognition.

A true flagship set.

“To do a rookie card, you've got to get the league and the union,” Dully explained. “So, we had to get the PGA Tour on board and the PGA of America.”

Easier said than done.

It took another nine months to get things squared away with the PGA Tour. “They didn't like it at all because they don't have control of the players, so they really didn't want to do it,” Dully said. If it wasn’t for Steinberg, who Dully says acted as a major advocate during the process, none of it would have happened.

Once the ink had dried, Upper Deck’s director of athlete relations Steve Sipe was teed up to execute on the deal.

Sipe had been with Upper Deck since nearly the company’s beginning, starting in 1990, and had managed all the company’s major athletes.

But even for a veteran such as Sipe, this was a whole new ballgame.

“It was like birthing a calf,” Sipe said, recalling the endless boxes he and his team needed to check in order to fulfill the contracts for autographs, photo-shoots and the like.

Sipe would go to tournaments such as the Houston Open, which was generally timed around the Masters, with a laundry list of autographs, shirts and memorabilia needed to build the trading card product and memorabilia business.

“I was just like a chicken with my head cut off,” Sipe said, describing the difficulties of tracking down players and grabbing them on the spot to sign hundreds of cards.

He compiled an excel sheet, which he still has to this day, of every player and agent from the time and their contact information. While easily found today, that resource represented the key to opening up the entire world to Sipe and Upper Deck — not to mention an added layer of legitimacy when they could reach players and their reps via phone rather than chasing them across the driving range.

Woods never posed any issues delivering on his end of the bargain.

“I just don't think there's anybody like him from a professional standpoint,” Sipe said. “If he was five minutes late, he’d call me to let me know.”

Eventually, time came for production.

Woods took a real interest in the look and feel of the design, not only of the cards, but the memorabilia and even the quality of his own signature.

“He played a big part in all that,” Sipe said. “He always liked to see it to the end and see the result of the product.”

The set had a total of 200 golfers featured in the base product followed by the SP Authentic release, which included limited-edition cards, autographs and inserts.

Noticeably missing from the set was Phil Mickelson, who was unhappy with the Tiger-centric product. He sat out and had his rookie card debut the following year.

Rather than provide a scribble to get through their run of cards, Sipe found golfers in particular were willing to give their autographs the proper time and were especially diligent.

For many, they had never been asked to sign at a volume nearly as significant as required for the card product.

“I think a lot of guys were just really happy to see our company take it as big as we did,” Stipe said. “They were glad to be giving old shirts that would otherwise be thrown away and see the made into swatch cards.”

There was another hurdle to clear if Upper Deck truly wanted to claim their Woods card as his true rookie. In the absence of mainstream releases, collectors had found more niche cards to act as the stand-in for a typical rookie card, one of which being his "Sports Illustrated for Kids" issue.

Gardner and the team went to Beckett to hash things out, negotiating for the company to designate the card as the true rookie and prior releases as an XRC. Beckett obliged, perhaps motivated to do so after Upper Deck offered to finance the first six of their golf magazine productions.

The release was split into two sets: Base and SP Authentic.

The base set featured 200 cards. Among them were not only Woods’ rookie card, but 44 others,. including Sergio Garcia and Mike Weir — a result of the long drought between licensed releases. It featured a few subsets and a limited number of autographs and memorabilia cards, including a full 30-card insert set devoted to Woods called “Tiger’s Tales.”

When the base set was released, Upper Deck sold 58,000 cases on its first day. Good enough to account for the entirety of Woods’ guaranteed $15 million contract, plus another $10 million or so sprinkled on top.

A few months later, Upper Deck followed up with the SP Authentic set, the high-end product that remains a source of cardboard gold today.

Filled with the most valuable golf cards ever created, namely Woods’ autograph gold parallel numbered to 25, the company raked in another $13 million or so to close out the inaugural year.

“There was no such thing as a golf card collector before that 2001 Upper Deck Golf set was released," said Ryan Carey of Golden Age Auctions. "It changed everything.”

Prior to the Upper Deck set, the last true mainstream licensed release (with respect to the 1992 Pro Set) was 1981 Donruss Golf, which was the sport's first modern release and featured the rookie card of Jack Nicklaus, though it got no traction. The reason for the lack of cards can in large part be chalked up to the athletes being independent contractors, far more difficult to organize into a licensed set than a sport like baseball with which a company can collectively bargain.

The bet on Tiger never felt like a particularly risky one to Gardner, who wasn’t even impressed all these years later at the sales totals.

“We knew it was going to be big,” Gardner said. “I mean, he was so, so hot at that point. He was winning everything.”

These days, when Gardner sees a big sale from the set or one of the cards come in for grading at Beckett, where he currently works, he hardly thinks about the massive sales volume. It’s the impact of the set that sticks with him.

“Very rarely do you get the opportunity to have a hand in bringing something to the market that's going to have a lasting stay,” Gardner said. “It's going to be a legacy in this business forever.”

Will Stern is a reporter and editor for cllct.