“Curt Flood stood up for us.”—Hall of Famer Ted Simmons.

Irony is almost as common to baseball as are the bat and the ball. Few examples remain more profound than one eight-player trade between the Phillies and the Cardinals in October 1969 that ended up changing the game for the men who played it.

The Phillies’ side of the deal included sending Hall of Fame-worthy third/first baseman Dick Allen to the Cardinals, whose package to the Phillies included seven-straight Gold Glove center fielder Curt Flood.

To Allen, whose Philadelphia experience was unconscionably brutal even by the norms of 1960s’ racial growing pains, the trade equaled the Emancipation Proclamation. To Flood, whose St. Louis experience included planting roots and owning and operating a portraiture studio in the city, the trade equaled what his eventual wife calls “like someone putting a knife in his stomach, or your mom throwing you away. It was that kind of deep hurt.”

Judy Pace was a groundbreaking black television actress (she had a prominent role in the popular television serial Peyton Place in its final season) and Flood’s girl friend for three years by the time Flood decided he wasn’t just a piece of livestock to be sold or dealt at will. They parted when Flood hied to Spain during his reserve clause battle but reconnected and married in 1986, eleven years before Flood’s death of throat cancer.

And Mrs. Pace-Flood thinks a fresh Hall of Fame election makes it more possible for her late husband to earn the honour as a baseball pioneer. “I’m so happy that Marvin [Miller] got in,” she tells William C. Rhoden, longtime New York Times sports columnist now writing for The Undefeated. “I want Curt to follow. There’s unfinished business.”

That business began fifty years ago today, when Flood—writing on the stationery of his portraiture studio—sent commissioner Bowie Kuhn a slightly early Christmas present, refusing to just report to the Phillies like a good little boy and rejecting the idea that he was mere property. “I believe,” he wrote, “that any system which produces that result violates my basic rights as a citizen and is inconsistent with the laws of the United States and of the several states.”

The Curt Flood letter to commissioner Bowie Kuhn.

To those who believe to this day that the Flood letter was really Marvin Miller’s handiwork, Mrs. Pace-Flood has a reply: “People ask about the letter, they don’t want to believe that he wrote that letter,” she tells Rhoden. “They want to know if Marvin Miller wrote the letter or if Marvin gave him the ideas. No. Marvin did not write the letter. Curt was brilliant.”

Arguably, Flood was the National League’s best defensive center fielder who wasn’t named Willie Mays in the 1960s. He won those seven Gold Gloves consecutively from 1963-69. As would future Hall of Famer Ozzie Smith at shortstop, Flood likewise made himself into a respectably fine hitter as the years of his career went forward. And there was more to him than just a rangy-squared outfielder.

“Flood was a quiet man, a deep thinker, and an independent cuss,” wrote John Helyar in The Lords of the Realm, published three years before Flood’s death. “He told friends on the club that he’d refuse to go if the Cardinals ever traded him. He’d quit before he left St. Louis. He had strong ties to the city, after playing for the Cardinals since 1958, and had begun a photographic and art business on the side. Flood was an outstanding portrait painter, whose rendering of [Cardinals owner] Gussie Busch hung in the saloon of the owner’s yacht.”

Let it be said that, even in the era when owners tended to be paternalistic when not dismissive of their hired hands on the field, Busch was somewhat anomalous in how he treated his players. He treated them like princelings, even if you considered that it was patrician patronage.

Busch put baseball’s first million dollar payroll on the field in 1968. He footed the bills for private rooms in top hotels when the Cardinals made road trips. Their homecomings included each player getting a free case of one of his Anheuser-Busch beers. And when the jet age arrived, Busch—who’d previously attached his luxury Pullman car Adolphus to trains for Cardinals players to travel in—flew them aboard charter jets.

He also helped Hall of Famer Stan Musial get into the restaurant business, when Musial bought into the St. Louis steakhouse where among other things fellow Hall of Famer Yogi Berra (a native St. Louisian) met his future wife. He helped Flood start his portrature business. He rewarded Roger Maris for two fine seasons as a Cardinal to finish his troubled career with a particularly profitable Anheuser-Busch distributorship after Maris retired.  He’d hand Hall of Famers Lou Brock a yacht and Bob Gibson a luxurious motor home upon their retirements.

And after the players threatened a spring 1969 strike over getting a hike in the owners’ contribution to their pension plan, a hike they eventually got when they could still high tail it to the spring camps and get into game shape, Busch responded by walking into his players’ spring training clubhouse in St. Petersburg with a few brewery directors, and delivering a lecture that only sounded the essence of calm reason.

It was really an old-fashioned patrician dressing down to the plebeians. “I hope that many millions of fans will retain their loyalty to baseball,” Busch was quoted as telling them. “We are going to do everything we can to make sure they do . . . I don’t react well to ultimatums. I don’t mind negotiations—that’s how we get together—but ultimatums rub me the wrong way, and I think ultimatums rub the fans the wrong way . . . ”

When reporters also present asked for comments, not one Cardinal said a word, probably too stunned to speak. “One of the players,” Helyar wrote, “stood there in a particularly raging silence. His name was Curt Flood.” Flood himself held out on his own for a raise for 1969 and got it, but Busch’s clubhouse speech sounded to him as though he “had been telling us to behave or get out. I no longer felt like a $90,000 ballplayer but like a green recruit.”

Flood became a Cardinal in the first place thanks to a 1957 trade that sent him there from the Reds in a five-player swap, and he’d sworn he’d do what it took never to be traded again. Now, after the 1969 Cardinals finished fourth in the new National League East, as Helyar quoted him, Flood told a friend, “There ain’t no way I’m going to pack up and move twelve years of my life away from here. No way at all.”

By November 1969, Flood called Miller to say he wanted to challenge baseball’s abused reserve system, by which the owners used the actual reserve clause’s one-firm/one-option year on player contracts to bind them for life or until the owners saw fit to trade or sell them. The Players Association agreed to foot the bill for Flood’s legal expenses, but Flood wanted to try his luck with Kuhn first. Hence the letter. And, hence, Kuhn’s reply just prior to New Year’s Day, as legendary sportswriter Red Smith put it: “Run along, sonny, you bother me.”

Known officially as Flood vs. Kuhn, the case went all the way to the U.S. Supreme Court. Before it was decided, the Cardinals were hit with a 1972 contract holdout, a 21-year-old catcher who’d just established himself as the number one Cardinal behind the plate. Before the kid was finished he’d expose another rupture in the owners’ armours.

Ted Simmons wanted $30,000; the Cardinals wouldn’t go much past $20,000. Simmons played under an automatic renewal, unsigned. As his season grew more torrid, he got a shock at the All-Star break, when he was in Atlanta as the NL’s reserve All-Star catcher: the Cardinals were ready to hand him $70,000: the $30,000 he wanted for 1972 and $45,000 for 1973.

With Simmons’s new signing the Cardinals betrayed a secret: the owners would rather open the vaults and hand a kid seventy large than let him even think about a reserve clause test. Then came the bad news for Flood, whose legal team included former Supreme Court justice Arthur Goldberg: the Supreme Court ruled against him.

The good news: Flood kicked a door open just a little bit. The Court itself called the reserve clause “an anomaly” and “an aberration” but decided it should be remedied by Congress. Which was akin to sending a lunch argument between two sharks to be remedied by a barracuda. Someone among the owners who didn’t have oatmeal for brains tried to warn them. “As the champagne corks popped,” Helyar wrote, “[owners’ negotiator] John Gaherin still cautioned: Flood’s defeat hadn’t brought an end to the forces of change; it had only bought them some time.”

Hall of Fame pitcher Catfish Hunter would kick the door open further after the 1974 season. When Athletics owner Charlie Finley reneged on a contracted-for insurance payment to Hunter, he took it to arbitration—and won, with the arbitrator declaring the contract breached and Hunter a free agent. Kuhn’s failed bid to get it overturned failed when Miller threatened a lawsuit.

Thus Hunter became the target of a bidding war that brought Hunter offers of, essentially, the galaxy, safe passage through the Cardassian Empire, grazing rights on Bejor, and a fleet of luxury starships. Kidding. Sort of. Hunter ended up taking the third most valuable package among the offers, from the Yankees, because of the money distribution he wanted including an annuity for his children’s education.

Hunter taught the world what a top of the line baseball player could get on a fair and open job market in a very profitable industry, in essence. All that was left was for some player, any player, to have the moxie to chase it for reasons having nothing to do with breach of contract and everything to do, more or less, with treating the reserve clause in strict interpretation. Meaning that the contract expired legally after the player had played his mandated first year and his team-optioned second year.

After the owners continued stalling on salary arbitration, which Gaherin himself believed might have forestalled the absolute end of the reserve system, one of the National League’s best pitchers refused to sign his 1975 contract, after being enraged when Dodgers general manager Al Campanis “injected a deeply ‘personal issue'” into their talks.

From that moment Andy Messersmith refused to talk to anyone lower than Dodger president Peter O’Malley. He also refused to sign any deal that didn’t include a no-trade clause, refusing to let the Campanises determine his career path. Messersmith pitched without signing a 1975 contract no matter how much money the increasingly edgy Dodgers offered as the season went on. (It may have reached as high as $550,000 over three years.)

This was no ordinary pitcher. Messersmith led the 1975 National League in shutouts, complete games, and innings pitched, with a 2.29 earned run average, a 3.09 fielding-independent pitching rate, and the lowest hits-against-per-nine rate in the league with 6.8. Not until August 1975 did Miller present himself to Messersmith, when the pitcher was the last unsigned player to remain unsigned and finally agreed to file the grievance seeking free agency.

Arbitrator Peter Seitz tried to persuade the owners to take the case away and negotiate, even offering to be the mediator if they did. They didn’t, and Messersmith won. Ted Simmons nailed it in one simple statement: “Curt Flood stood up for us. [Catfish] Hunter showed us what was out there. Andy showed us the way.”

“I never went into this for the glory and betterment of the Players Association. At the start, it was all personal,” Messersmith said in due course. “The money was incredible, but they wouldn’t being the no-trade clause to the table . . . Now I understood the significance of what this was all about. I was tired of players having no power and no rights.”

Messersmith finished what Flood began. Today, with Miller finally elected to the Hall of Fame despite his late-life demurrals (he died in 2012), there’s a small swell hoping that Flood will receive the same honour as a baseball pioneer. Including new Yankee pitcher Gerrit Cole, who signed a deal about which Flood himself could only have fantasised, nine years and $324 million, average annual value $36 million.

When Cole was introduced formally as a Yankee, he paid tribute to Flood, Simmons, Hunter, and Messersmith. “[C]hallenging the reserve clause was one of the first stepping stones to ultimately the system we have today, which I believe brings out the genuine competitiveness that we have in baseball,” Cole told the presser. “I just think it’s so important that players know the other sacrifices that players made in order to keep the integrity of the game where it is.”

Flood wasn’t entirely alone during his challenge. Teammates supported him morally. So did Dick Allen, to whom the trade was liberation day. Trial testimony on Flood’s behalf came included from Hall of Famers Jackie Robinson (Mrs. Pace-Flood once said his testimony almost brought Flood to tears, coming from his personal baseball idol) and Hank Greenberg. ABC Sports broadcast legend Howard Cosell backed Flood publicly.

But Flood still felt as though on the threshold of a nightmare. “You couldn’t even use the word nervous,” Mrs. Pace-Flood said in a 2017 interview. “It was completely draining for Curt, mentally and physically. It was as if his whole world was going to disappear. All that he had worked for, all that he loved, all that he ever wanted to do—those things were hanging in the balance with the outcome of this case.”

Curt Flood, in the Senators’ dugout, next to his manager—Hall of Famer Ted Williams.

After sitting 1970 out, Flood actually tried a baseball comeback—with the Washington Senators, whose otherwise capricious owner Bob Short delivered perhaps the finest gesture of his baseball life on Flood’s behalf. Short made a deal with the Phillies to get negotiating rights to Flood. Then he made Flood an offer he couldn’t refuse: He offered Flood $100,000 for 1971, agreed to pay the money no matter what, and agreed further that, if they couldn’t come to terms for 1972, he’d make Flood a free agent.

The kicker, according to Tom Deveaux’s The Washington Senators 1901-1971: Short wouldn’t put that agreement in writing, since it would violate the rules of the time. And, according to Flood himself, Short would deny those extra conditions existed if they were made public.

The worse news was that Flood no longer had it, and he knew it a little too sadly. He left the team on 27 April, leaving Short a note saying he’d tried but the long layoff proved too much, not to mention having run into financial trouble with his portraiture business. That was putting it politely. The business went bankrupt, and Flood also faced issues with the Internal Revenue Service over the home he’d bought his mother.

Flood bought a bar on Majorca to begin sorting out his shattered life, but in time he returned to America, tried broadcasting with the A’s for a spell, and reconnected with Judy Pace. He also became, of all things, the commissioner of two short-lived professional baseball leagues, the Senior Professional Baseball Association (1988-89) and the United Baseball League (mid-1990s).

“Flood seemed a strange choice to be commissioner of a league that desperately would need the assistance of the major leagues,” wrote Peter Golenbock in his book about the SPBA, The Forever Boys: The Bittersweet World of Major League Baseball as Seen Through the Eyes of the Men Who Played One More Time, published in 1991. “Later I would discover that many of the players considered themselves outcasts from baseball, so perhaps Flood’s choice as commissioner had been fitting after all.”

“Dred Scott in spikes,” George F. Will called Flood in 1993.

There was poetry and portent in the fact that Curt Flood’s career blossomed in St. Louis, the city where Dred Scott had taken his case to court. In 1966, the Cardinals moved into a new stadium that is located just a long fungo from the courthouse where Scott, a slave, argued that he had lived on free soil and therefore should be free . . . [Scott] was not the last time that the Supreme Court would blunder when asked when a man can be treated like someone’s property.

That is the question Curt Flood posed when the Cardinals tried to trade him. They said he had to go wherever they decided to send him. It had always been so, and always would be. He said, well, we’ll just see about that. He rose in rebellion against the reserve clause that denied baseball players the fundamental right to negotiate terms of employment with whomever they chose. He lost the 1970 season and lost in the Supreme Court, but he had lit a fuse.

Six years later—too late to benefit him—his cause prevailed. The national pastime is clearly better because of that. But more important, so is the nation, because it has learned one more lesson about the foolishness of fearing freedom.

Will observed wryly that what was once said of another player could have been said of Flood the center fielder—two-thirds of the earth is covered by water and the rest was covered by Flood. That was nothing compared to the flood he began when he stood on his hind legs and demanded, quietly but firmly, the rights of any working man or woman from the most obscure labourer to the most elevated chief executive officer.

Flood belongs in the Hall of Fame as the citizen who first told baseball seriously that denying a man the right to sell his services fairly and openly was, shall we say, un-American. So does the California guy who finished what Dred Scott in Spikes began, when Flood fired the second shot heard ’round the world one not-so-foggy Christmas Eve.