Chumps to Champs

by Bill Pennington

  The contract had been a sore point between the two men ever since, especially after Winfield had just one hit in 22 at-bats during the team’s loss in the 1981 World Series, and also failed in the 1980s to lead the Yankees to a championship, like Steinbrenner’s other headline free-agent purchase, Reggie Jackson. In the middle of an important game in September 1985 that the Yankees were about to lose, Steinbrenner stood in the back of the Yankee Stadium press box and noted that Jackson was so productive in late-season clutch games, he was nicknamed “Mr. October.” He added, “Now I’ve got Dave Winfield—Mr. May.”

  But the dispute between the owner and one of the best players in baseball was more acrimonious than simple insults. Part of his contract with Winfield called for Steinbrenner to make annual payments of about $300,000 to Winfield’s foundation, which was set up to benefit impoverished youth. According to the contract, Winfield was also required to make regular payments to the foundation, which was to be operated in certain stipulated ways.

  By the mid-eighties, Steinbrenner and Winfield had clashed repeatedly over these terms and whether the foundation was doing what it was intended to do. The Yankees had also been complaining that the foundation was a front for employing Dave Winfield’s relatives. To which Winfield said, “Look at the Rockefeller foundations. Are you telling me there are no Rockefellers working there?”

  By 1986, Steinbrenner had dug in his heels and refused to make his mandated payments to the foundation. It was not an act of stinginess. Steinbrenner was one of the most generous of all sports team owners. He founded the Silver Shield Fund in 1982, which benefits the children of New York–area police officers and firefighters who die in the line of duty. Thirty-six years later, the charity continues to financially support hundreds of children annually. And for decades, Steinbrenner quietly paid for the college educations of countless children whose lives intersected with his in one way or another.

  In the early nineties, I was staying at Steinbrenner’s Tampa hotel and struck up a conversation with the restaurant lounge’s bartender. The bartender, who did not know she was speaking to a reporter, had been complaining to a waitress about Steinbrenner’s presence in the hotel that night. Having the Boss, as he loved to be called, in the house put every employee on edge, because Steinbrenner would sometimes barge into the kitchen to inspect the silverware or scrutinize the food prep. He might do a uniform check.

  “Everyone is so goddamned relieved when he leaves for the night,” she said.

  Added the waitress: “Such a pain in the ass.”

  The bartender smiled. “But I guess I should be nicer,” she said. “When my husband got sick and couldn’t work last year, Mr. Steinbrenner heard about it and said he would put my son through grad school.”

  The waitress piped up as well. “He did the same thing for my daughter. Paid all of her tuition so long as she got A’s and B’s. She had to bring him a report card, but a few days later, her college got a check.”

  So Steinbrenner’s refusal to pay the David M. Winfield Foundation was not a case of the Boss being miserly. It was another chapter in the bitter, costly Winfield-Steinbrenner feud.

  The impasse soon led to a series of suits and countersuits between Winfield and Steinbrenner. It was at this moment that Howie Spira, the former foundation employee, called Steinbrenner’s office and offered “dirt on Winfield” that would presumably help the Yankees’ owner win his dispute with his star outfielder.

  Spira was an odd, nebulous character, a thin, gangly twenty-six-year-old from the Bronx who, it turned out, had considerable gambling debts. Spira was often at Yankees home games with a radio reporter’s credentials, although few of the regular media members had any idea what he did. He had been a publicist for the Winfield Foundation, although Winfield later called him more of a “go-fer.” Most of all, Spira was quiet, someone seen but seldom heard.

  But in the spring of 1987, Spira met with Steinbrenner several times and convinced him he could prove various Winfield Foundation improprieties. In June, Spira, Steinbrenner and Yankees lawyers took their allegations to the Manhattan district attorney.

  The legal maneuvering that followed clouded three Yankees seasons, a time when Winfield, along with Don Mattingly, was the team’s most respected player—in the Yankees’ clubhouse and around the league.

  Finally, on September 6, 1989, arbitration resulted in a settlement of the Steinbrenner and Winfield lawsuits, with Steinbrenner paying the $600,000 he had withheld from the foundation and Winfield agreeing to pay about $200,000 he had not contributed.

  One long, disruptive Yankees distraction had come to an end.

  Or so it seemed. The détente between Winfield and Steinbrenner was short-lived. In January 1990, Spira began pestering Steinbrenner for money, insisting that Steinbrenner had reneged on a promise to give him a job. Spira threatened to disclose tape recordings of their telephone conversations about Winfield. He also contacted several newspapers, promising to relate his story, with the tapes, for $50,000. No publication took him up on his offer. But eventually, Steinbrenner wrote Spira a check for $40,000. At first, Steinbrenner said he had given Spira the money “out of the goodness of my heart,” because he was trying to help the financially strapped Spira. Later, Steinbrenner said he had paid to keep Spira from reopening the details of the battle with Winfield and to prevent Spira from disclosing embarrassing information about former Yankees employees.

  Whatever Steinbrenner’s true intentions were, he also contacted the FBI and asked it to investigate Spira. And indeed, five days after the Daily News story in 1990, Spira was indicted by a federal grand jury for trying to extort money from Steinbrenner, and from Winfield as well.

  The next day, in an ominous revelation, baseball commissioner Fay Vincent, who a year earlier had assisted then commissioner Bart Giamatti in the investigation that led to Pete Rose’s permanent expulsion from baseball, said his office had begun looking into the Steinbrenner-Spira connection.

  “We’re happy to have it looked into,” Steinbrenner said of Vincent’s inquiry. “I understand he’s going to look at the whole picture where Spira’s concerned, not just my involvement.”

  Asked by the New York Times if he thought there might be a chance he would be disciplined for his dealings with Spira, Steinbrenner responded: “None whatsoever, according to my people. From what I understand, we’re not worried about it.”

  Since the interview was conducted over the telephone, it is not known if Steinbrenner’s frown/smile reflex had kicked into gear during his answer.

  What is known is that a week later, John Dowd, a Washington lawyer who conducted the six-month Rose investigation and compiled a dossier that filled seven volumes, began interviewing various parties associated with the case, including Spira.

  At roughly the same time, the 1990 Yankees, no longer locked out of their spring training home in Fort Lauderdale, were finally convening for the first time.

  At least most of them were there. The team’s best pitcher, Pascual Pérez, could not leave the Dominican Republic because of visa and legal problems. Or something like that. Pérez earned the nickname “Wrong-Way Pérez” after a 1982 incident when he missed an Atlanta Braves home game as he circled—three times—a beltway interstate looking for Atlanta–Fulton County Stadium. Pérez had also twice been suspended for cocaine use in the eighties. In 1990, he would arrive in Fort Lauderdale a week late.

  Pérez, who had the comical habit of checking a runner on first base by bending over and peering through his legs, was easily the riskiest of the bets the Yankees were making in 1990. But he was not the only one.

  Another veteran starting pitcher, Tim Leary, had been acquired from the Cincinnati Reds. Leary had been brilliant in 1988, when he had a 17-11 record. But in 1989, he had slumped to 8-14. Which pitcher were the Yankees getting?

  Dave LaPoint was the third starter, and he was coming off shoulder surgery after a season when he had a 5.62 earned run average. LaPoint’s record was 38-53 in the previous f
ive seasons.

  Andy Hawkins, the fourth starter, had been a steady workhorse for the Yankees in 1989, winning 15 games and losing 15. Chuck Cary, the fifth, was thirty years old but had just 14 career decisions, eight of them defeats.

  The strength and reliability of the Yankees’ bullpen was similarly uncertain. Dave Righetti, the team’s All-Star closer since 1984, had worried the Yankees with his inconsistency in 1989.

  As for the batting order, there were an equal number of paradoxes and enigmas. The right fielder Jesse Barfield had once hit 40 home runs, but that was four years earlier. Barfield still had power, but his batting average had slumped to .234. Winfield had been an All-Star selection every year in the 1980s except for one, and that happened to be 1989, when he did not play a game because of major back surgery.

  No one knew what to expect from Winfield in 1990, including Winfield himself. “I feel fine and you see me out there swinging the bat and playing the field,” Winfield said in spring training. “So it looks like me. But I’ve got a long way to go until I am actually me again.”

  In many ways, the 1990 Yankees were still lurching from the 1989 trade of Rickey Henderson, the team’s most versatile, explosive, talented—and irrepressible and disruptive—player.

  Henderson had never truly been happy as a Yankee unless his longtime mentor Billy Martin had been the manager. In other years, Henderson was finicky, moody and mercurial. In 1989, he was particularly in a funk—oft-injured, listless and underperforming. He, too, seemed worn out by the nonstop turmoil. So, as gifted as Henderson was, the Yankees felt compelled to deal him to the Oakland Athletics. The problem was that the Yankees received almost no one of prominent value in return, acquiring pitchers Greg Cadaret and Eric Plunk and outfielder Luis Polonia. Cadaret would end up compiling a 22-23 record in four seasons with the Yankees. Plunk would be 15-13 in three Yankee seasons. As a Yankee, in 1989, Polonia had been arrested and jailed for having consensual sex with a fifteen-year-old in Milwaukee.

  The deal was crafted by then Yankees general manager Bob Quinn, who was also on his way out of the Yankees organization.

  Henderson’s departure left a gaping hole in the Yankees lineup and diminished their defense, but most of all, it meant the Yankees were no longer feared by American League teams. Opposing teams viewed Henderson, who would eventually score more runs and steal more bases than any player in major league history, as a dreaded pest. He especially unnerved pitchers.

  With a career on-base percentage of .401, Henderson, who ranks second all-time in walks, was a constant presence on the basepaths for the Yankees from 1985 to 1989. It seemed like Henderson was standing on first or second base about half the time that Winfield or Don Mattingly came up to bat in that period. And since Henderson led the major leagues in runs in three of those seasons, it seemed as if either Winfield or Mattingly always drove the speedy Henderson home with a hit.

  It was the Yankees’ only established formula for success. In Henderson’s absence, a new formula for success had yet to be developed.

  Winfield lamented Henderson’s exit, but he was far too busy trying to rebuild his body from a year’s layoff and serious back surgery. The Yankee who missed Henderson the most—on the field at least—was Mattingly, the heart and soul of the team.

  Mattingly, as captain of the team, and because he was an ultrapolite Midwesterner, was not one to decry or belittle the players remaining in Yankee pinstripes. But when he came to the plate, he knew Henderson was no longer on the bases to harass the opposing pitcher into a mistake. He knew the Yankees lineup was now more toothless. Randolph, a shrewd number two hitter behind Henderson, was also gone. Mattingly, who had recently signed a five-year, $19 million contract that made him the highest-paid player in baseball, knew that Henderson’s daring swagger and Randolph’s competent batsmanship were no longer setting the table for him and other Yankees hitters.

  Mattingly saw a team that was losing its bite and beginning to doubt itself. The Yankees, lacking direction, were a team cast adrift. “The lack of a plan, the constant changes, the impact of all that had been building,” Mattingly said in 2016. “But something in and around 1990 was worse. There wasn’t the right plan.

  “Or there wasn’t a plan. Maybe that was the real problem. We needed a plan. We needed someone who could plan.”

  3

  Buck Naked

  FOR THE FIRST Yankees game of the 1990 season, there was a new presence, one altogether out of place, sitting in the last row of the press box. The new face was neither a member of the news media nor a front-office employee.

  It was thirty-three-year-old William Nathaniel Showalter III.

  He was a new invention in baseball: the eye in the sky.

  The Yankees were one of two teams that used this novel scouting tool. It meant placing a coach behind home plate and about 50 feet above the field—roughly at the mezzanine level in a baseball stadium—where the coach could better observe the positioning of the players and the signals from the base coaches and managers in the dugout, and also take notes on the strengths and deficiencies of both teams as they reacted to various game situations.

  By Major League Baseball rules, Showalter was forbidden from communicating with the rest of the coaching staff during games, but he wrote elaborate, copious reports on what he saw from his perch above the diamond.

  The job paid $50,000 a year, or half what the other coaches were earning. “And in New York City, $50,000 didn’t go far—I was losing money,” Showalter said.

  Years later, Showalter had his doubts about whether manager Bucky Dent—or anyone—was reading his detailed, meticulous accounts of the movements he perceived during games. But as it turned out, someone named Steinbrenner was intently scouring Showalter’s missives on his view of the game within the game.

  And that someone was not George Steinbrenner, but George’s elder son, Hank. And that mattered a great deal down the road.

  Buck Showalter had been a Yankees minor league manager and player—he picked up his nickname in the minors because teammates said he liked to walk around the locker room “buck naked.” When called up to be the eye in the sky in 1990, Showalter would be in uniform and on the field before games, pitching batting practice or hitting ground balls to infielders. Then he would shower and change into civilian clothes and take an elevator to the press box.

  Most press boxes are loud, jocular places where the repartee is mostly nonstop—at least until late in games, when the noise of fingers pecking at keyboards replaces the banter. But Showalter in this setting generally kept to himself, sitting as far from the working press as possible. He wasn’t antisocial or distrustful; Showalter actually enjoyed interacting with reporters. He is a gifted storyteller who would have been at home in Casey Stengel’s 1950s prime.

  But the eye-in-the-sky assignment was a crucial gig to Showalter, and like the high school principal’s son that he was, he took it somberly and seriously. When the game commenced, Showalter would grow quiet and intense. He stared straight ahead with a determined, fixed mien, and his eyes would dart around the field even as his head and body would remain motionless. He sometimes held a stopwatch, and he wrote continually in one of two loose-leaf notebooks. One of the notebooks had drawings depicting the infield diamond and the outfield configurations. In the other, he would make X’s and O’s with sketched lines showing the paths of base hits, ground balls and throws.

  Nowadays, every team has a gaggle of employees who analyze the same game data as it is gathered by sophisticated, baseball-specific software programs that collect statistics on launch angles, bat speeds and vector mathematics, which would have seemed unimaginable to Showalter at the time. In 1990, he was helping the Yankees get started by doing it the hard way: in longhand notes as the newly minted eye in the sky.

  After games, Showalter would descend to the clubhouse, to quiz his fellow coaches about why certain strategies unfolded as they did in the game. And then, since Showalter also kept his own journal on a baseball season
, he would make more personal notes, mostly on things to remember and lessons to absorb. He sometimes awoke at night to jot down a new observation that popped into his head.

  There was much to absorb, catalog and process—for a very good reason. Showalter had never been in the major leagues before.

  Showalter was born in 1956 in DeFuniak Springs, Florida, and he forevermore spoke with the Southern accent of someone whose Florida panhandle hometown was five miles from the Alabama border.

  He was a sports star in a racially mixed community that was segregated, not by law but by custom. Showalter’s father was known as Bill, and his only son was called Nat. Bill Showalter had been a football star at Milligan College in Tennessee. When World War II began, he enlisted in the US Army, where he was assigned to the famed 1st Infantry Division, a combat unit immortalized in the film The Big Red One. Bill Showalter was part of three monumental invasions, at Normandy, Sicily and Algiers. He was awarded a Bronze Star for bravery, a character trait he did not exhibit only on the battlefield.

  As principal of the middle school and then the high school in the tiny Florida town of Century, where Bill lived with his wife, three daughters and son, he knew what federal laws said about the mandated racial makeup of schools across the land. Century had not been in accord with those laws, and Bill took it upon himself to lead the fight to desegregate Century’s schools. As just one example, when the town’s schoolteachers, hell-bent on reform, went on strike, Bill went on strike with them.

  It was not a popular stand in many parts of Century.

  The Showalters’ household phone rang throughout that first night of the strike, and Bill took the calls and listened to the threats. But when the strike ended, he went back to enforcing the desegregation plan he had helped devise.

  When his son was eleven years old, he put him in the front seat of the family pickup truck and drove to an all-black neighborhood to play in organized baseball games, even if it meant that there was just one white face on the field. “There’s another world out there, son, and the more you know about it, the better off you’ll be,” Bill Showalter said.