The New York Yankees’ recent signing of prized free agent Gerrit Cole only adds to their fascinating history of pursuing marquee free agent pitchers. It has been a checkered history, fraught with failed dalliances with pitchers who wanted no part of the city (Greg Maddux), flops who couldn’t deal with the stress of New York (Ed Whitson), failures due to career-cutting injuries (Don Gullett), and a number of unquestioned successes (Goose Gossage, Jimmy Key, David Cone, and Mike Mussina).

It’s a long and twisting history, one that can be traced back to the winter that followed the 1974 season. That’s when a Hall of Fame right-hander became the game’s first true free agent, under special and surprising circumstances that ranged from the mysterious to the bizarre.

As the Oakland A’s headed into their third consecutive World Series that fall, a shadow hovered above the franchise, and more specifically team owner Charlie Finley. For reasons that remain nebulous to this day, Finley failed to make a $50,000 life insurance annuity payment on behalf of Jim “Catfish” Hunter, even though it was clearly stipulated in the ace pitcher’s contract. Supposedly, Finley was upset about having to pay an additional $25,000 in taxes, but that amount of money would soon become small in comparison to the kind of money Hunter would make on the open market.

Realizing he had failed to make the deadline, Finley attempted to make the insurance payment after the fact. Hunter and his agent refused to accept the late payment. With the full support of the players union, Hunter and his agent announced the failed payment amounted to a violation of his contract. In other words, the failed payment would make Hunter a free agent after the World Series.

Finley called the failed payment a mere “technicality,” but Hunter and his agent felt otherwise and filed a grievance with the Players Association. On November 19, the two sides made their arguments in front of independent arbitrator Peter Seitz. (That’s the same Peter Seitz who would rule in favor of Dave McNally and Andy Messersmith two years later, paving the way for the widespread free agency of the modern game.) Three weeks after hearing the evidence in the Hunter case, in a bombshell announcement, Seitz declared Hunter an immediate free agent who was now free to open negotiations with any and all of the then-24 major league team.

The ruling essentially ended Hunter’s career with the A’s; he previously had announced he had no intention of going back to Oakland because of Finley’s increasingly contentious style of management. A’s players realized they had lost their No. 1 starter, the same man who had recently won the American League’s Cy Young Award. Hunter’s friends also understood he likely would sign with one of the large-market clubs in New York or Chicago, or newly free-spending teams like the San Diego Padres or Montreal Expos, both interested in making a splash by spending on a Hall of Fame talent.

In response to the Seitz decision, an angry Finley announced he would sue any team that attempted to sign Hunter. Acting out of desperation, Finley sought a temporary injunction to prevent Hunter from negotiating with other clubs, but a Superior Court judge in Alameda County turned down his request. Finley then announced he would appeal the Seitz decision on the grounds the independent arbitrator had exceeded his authority in making Hunter a free agent.

Commissioner Bowie Kuhn, in a rare occurrence, actually found himself in agreement with arch-enemy Finley. Kuhn advised the 23 other major league teams to refrain from negotiations with Hunter. The commissioner’s directive angered Players Association leader Marvin Miller and Hunter’s team of four lawyers, headed by J. Carlton Cherry, a previously little-known 68-year-old attorney who was now becoming a major star himself.

The commissioner’s edict did not last long. A few days later, Kuhn reversed his decision and gave teams his blessing to negotiate with Hunter. That opened the floodgates. There was no delaying, no need to double check with the talent evaluators about the value of someone like Hunter, a durable workhorse and the unquestioned ace of a dynastic team. Within three hours of Kuhn’s reversal, 12 teams (half of those in existence) contacted Cherry at his office in Ahoskie, North Carolina.

As with the signing of Cole, the pursuit of Hunter moved quickly. In fact, at a time when contracts were simpler, the free agent chase moved at lightning speed. By the time Christmas had come and gone, nearly every one of the 24 major league teams had called Cherry’s office to make an opening offer. Both New York clubs, the Yankees and the Mets, made it clear they wanted Hunter. Meanwhile, some smaller-market teams advised Hunter that he should avoid a large city like New York; Hunter himself was a country boy from North Carolina who had grown up in a rural area where he enjoyed fishing and hunting. As with the pursuit of so many superstar free agents over the past 45 years, the argument of “big-city money” vs. “small-market comfort” had already begun.

Several major league teams tried to use their own players and coaches—those who were friends of Hunter— to persuade the ace right-hander to sign with them. For example, the Milwaukee Brewers told their first baseman, Mike Hegan, a former Athletic and onetime teammate of Hunter, to meet with Catfish and persuade him on the benefits of living in Wisconsin. Hegan agreed to do so. In the meantime, the Cleveland Indians sent their ace, Gaylord Perry, Hunter’s frequent hunting companion during the offseason, to put on a full-court press. (Imagine a rotation headlined by Hunter and Perry. Hint: It would never happen.) The Padres dispatched of two representatives—manager John McNamara and coach Bill Posedel, both former Oakland employees whom Hunter had worked for—to meet with the pitcher.

By the time the personal recruitments had ended, 48 baseball representatives had descended on the small tobacco-farming community of Ahoskie, which suddenly had become the center of the baseball universe.

Open minded to the extreme, Hunter said he would consider proposals from any major league team. Like so many free agents of today’s game, Catfish wanted the total package—and not just money. Hunter and his agent announced they would consider endorsement and investment possibilities, the stability of a team’s ownership, and the quality of the team. Obviously, the better the team, the better the chance of signing Hunter.

Within a few days, Hunter narrowed his choices down from over 20 teams to only eight, a group that surprisingly included the A’s. The presence of the A’s on the list stunned many, but Hunter’s lawyers explained they had heard rumors Finley might sell the team, thus opening up an avenue for Hunter to return to the only major league franchise he had ever known.

A Hardball Times Update by Rachael McDaniel Goodbye for now.

According to one rumor, Finley was considering the sale of the A’s to a group headed up by former San Francisco Giants manager Herman Franks, who had become independently wealthy through a series of sound investments. Those rumors of a sale turned out to be wishing thinking. In truth, Finley was not about to sell the franchise. When Hunter and his lawyers realized Finley would remain in charge, they eliminated the A’s from consideration.

As the negotiating process reached the closing days, Hunter reduced his list of potential teams to five: the Padres, Royals, Braves (who had yet to be purchased by Ted Turner), Indians (not known as big spenders), and Yankees. It was an interesting list, one that excluded both Chicago teams and both Los Angeles-area teams. So much for the idea that only large-market teams would have a chance of signing the game’s first free agent.

On New Year’s Eve, fewer than three weeks after Hunter had become a free agent, the largest bidding war in the history of the game ended. Holding a lavish press conference that bordered on media circus, the Yankees announced they had signed Hunter to a five-year contract worth $3.75 million, including a signing bonus of $1 million. While the numbers seem paltry in comparison to the dollars of today (especially to Cole’s $324 million deal), Hunter’s 1975 contract represented a financial boon previously unseen in a game in which full-fledged free agency did not yet exist, and where the reserve clause kept players bound to their teams year after year after year.

The decision surprised some, especially when it became known that the Royals and Padres had offered more money than the Yankees. If Hunter had signed with the Royals, he would have joined a rotation already featuring a young Steve Busby and Paul Splittorff, while in San Diego, he would have completely changed the dynamic for a team that had no one approximating ace status. So why did Hunter reject the Padres and Royals? According to some, Hunter liked the idea of staying on the East Coast, which put him closer to his home in North Carolina, where he had been born.

Others were surprised the Yankees won out given Hunter’s previous comments about playing in New York. In 1971, Hunter had publicly expressed fear about leaving his hotel room during Oakland’s stays in New York City. “New York still scares me to death,” Catfish had told Sport magazine.

Three years later, Hunter had changed his mind. But even more than his own maturation and simple geography, Hunter had been influenced greatly by the Yankees’ director of scouting, Clyde Kluttz. It was Kluttz who originally had signed Hunter for the Kansas City Athletics in 1964. And it was Kluttz who told Hunter the Yankees were the best choice. “He never lied to me,” Hunter told Sport in describing his relationship with Kluttz. “He’s my friend. That’s why I signed with the A’s, and that’s why I signed with the Yankees.”

Kluttz had convinced Hunter New York was not only livable but would provide him with the recognition he could never receive in locales like San Diego or Kansas City. Former A’s teammates Hegan and Curt Blefary, both of whom had once played for the Yankees, also suggested Hunter could live in suburban areas around New York, such as northern New Jersey, with its benefit of having no state income tax. Thus, the Yankees won the bidding over 22 other major league teams, each of which had made offers on the Cy Young Award winner. Of all the big league teams, only the financially troubled Giants had not made Hunter an offer of any kind.

While some skeptics continued to question Hunter’s decision to sign with large-market New York, there were no such questions about the Yankees’ desire to sign Hunter. Owner George Steinbrenner, who had purchased the team only a year and a half earlier, was clearly the type who would spend whatever it took to return the Yankees to the glory the franchise had last enjoyed in the early 1960s.

Just as significantly, the Yankees had needed a No. 1 starter ever since Mel Stottlemyre had torn his rotator cuff in the middle of the 1974 season. (At the time, rotator cuff surgery had never been tried successfully, making it a career killer.) With Stottlemyre unable to pitch and forced into retirement, Hunter made perfect sense to fill the role of rotation anchor and ace. While the Yankees had been a good team in 1974, they were still considered at least two or three players away from championship caliber in 1975. The addition of Hunter drew them that much closer to becoming the favorite in the American League East.

So how did Hunter fare for the Yankees? In his first season with New York, he pitched like he had during his Oakland prime, posting a 2.58 ERA in a remarkable 328 innings, winning 23 games, and finishing second in the Cy Young Award balloting. As a team, the Yankees fell back in the standings by six games and won only 83 games that season, but none of that could be blamed on Hunter.

Hunter’s first season with the Yankees turned out to be the last dominating campaign of his career. In 1976, he was workmanlike and steady, giving the Yankees another 298 innings, but his ERA rose to 3.53. And then over the next three years, the heavy workload and a series of injuries took their toll, limiting him to a maximum of 22 starts in a season and declining efficiency. As Hunter’s contract expired in 1979, so too did his career, as he opted for retirement at age 33.

Based strictly on the numbers, it might be tempting to call Hunter a free agent disappointment with the Yankees. Yet, there is more to the story. Known for his down-home popularity among teammates and his thoroughly professional approach to the game, Hunter provided leadership to a group of Yankee players who had never won anything, making him an intangible factor on New York’s pennant-winning teams of 1976, ’77, and ’78. He also became a mentor to a young Ron Guidry, who would succeed him as the Yankees’ ace and emerge as the best pitcher on the planet in 1978. Without Hunter’s presence, it’s questionable whether the Yankees would have won the pennant in 1976 and whether Guidry would have achieved his Cy Young level in the late 1970s.

Of course, the Yankees will be expecting more tangible results from Cole in light of his record-setting contract for pitchers. Like Hunter was in 1975, Cole is entering his age-29 season. And like Hunter, Cole is right-handed. But that is where the similarities end.

Hunter was a finesse pitcher who relied on a terrific slider, superb control, and an ability to pinpoint his pitches. Cole is a power pitcher who throws a four-seam fastball in the high 90s, owns a wipeout slider, and can dominate opposing lineups in a way that is far different from Hunter’s more surgical approach. Cole also has relatively little mileage on his right arm. He has never thrown more than 212 innings in a season; Hunter, in stark contrast, never threw fewer than 234 innings from 1967 to 1974 and once reached a high of 318 innings during that span.

Based on their workloads, Cole seems unlikely to flame out in his early 30s the way Hunter did. But Cole’s burden remains high. He is expected to prolong his recent run as arguably the American League’s top starter (you can flip a coin between him and Justin Verlander) while also pushing the Yankees to at least one or two world championships during his time in the Bronx. Fair or not, that is the expectation, an expectation created by the phenomenon of free agency, something that began under odd circumstances with James Augustus Hunter and has reached a new level of frenzy with Gerrit Alan Cole.