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Daniel R Levitt

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  1. Daniel R Levitt
    This post is part of a series in which Mark Armour and I count down the 25 best GMs in history, crossposting from our blog. For an explanation, please see this post.
     
    [This one is from Mark]
     
    Frank Cashen had two stints running a big league baseball operation. In his first job he oversaw a budding great team as president and later kept it contending in the GM role as well. At his second stop he took over a long struggling franchise that needed a complete transformation. He succeeded at these two opposite challenges masterfully, meriting his status as one baseball’s best baseball ops executives.
     
    Cashen spent 17 years as a sportswriter in Baltimore, earning a law degree at night. In the late 1950s he went to work for Jerry Hoffberger, first running a couple of race tracks and later working as the advertising chief for Hoffberger’s brewery. When Hoffberger, a longtime minority owner of the Orioles, assumed control of the team in 1965, he asked Cashen, a brilliant and trusted executive who nonetheless had no experience in the business of baseball, to oversee it. Not long after, general manager Lee MacPhail left to work in the commissioner’s office, and Cashen promoted Harry Dalton to be the Orioles GM. Cashen was Dalton’s boss, but he needed the talented Dalton to run baseball operations. The team won four pennants and two World Series during the six years (1966-71) of this arrangement.
     
    After the 1971 season, fresh off three straight pennants, Dalton left to run the lowly California Angels, saying he wanted a new challenge. Rather than hiring a replacement, Cashen took over the GM duties himself. This was not a big surprise — Cashen had been intimately involved in the day-to-day work that Dalton had been doing.
     
    Although the Orioles were on a great run, the team was aging and would change rapidly over the next few years. Just a few weeks after taking over, Cashen traded star and leader Frank Robinson to the Dodgers, a move that Dalton recommended before he left. The team was stunned, and many blamed Robinson’s departure for their team-wide, year-long batting slump, dropping from a league-leading 4.70 runs per game to just 3.37, and a third place finish.
     
    But Cashen got them back over 90 wins the next three years, making key deals that landed Tommy Davis, Ross Grimsley, Lee May, Ken Singleton, and Mike Torrez. Together with youngsters Bobby Grich, Don Baylor, and Al Bumbry, and a few key holdovers (especially Jim Palmer) the team won division titles in 1973 and 1974, and took the Red Sox down to the wire before losing in 1975.
     
    After the season Cashen resigned and went back to work in Hoffberger’s brewery. Cashen left the organization in great shape, and they remained the gold standard for excellence throughout the system. Soon players like Doug DeCinces, Eddie Murray and Mike Flanagan would be joining the big club, keeping their great run going another decade.
     
    Cashen spent a couple of years out of the game before working in the commissioner’s office for two years. In early 1980 Nelson Doubleday, the new owner of the New York Mets, talked Cashen back into baseball, giving him complete control of the club (acting as both GM and the COO). The Mets had been a woeful team for four years, and in 1979 played before fewer than 800,000 fans (still the low water mark for the team). Cashen told ownership that he needed at least four years to turn the organization around, and he began by revamping the scouting and minor league systems. Over the next several years the Mets developed Daryl Strawberry, Dwight Gooden, Kevin Mitchell, Lenny Dykstra, Mookie Wilson, Rick Aguilera and several others.
     
    Meanwhile, Cashen made some early high-profile attempts to improve the big league team. He acquired sluggers Dave Kingman and Ellis Valentine in 1981, but neither helped much. Cashen dealt for George Foster in 1982, but the slugger’s days of stardom proved to be over. Cashen first hit the jackpot in June 1983 when he traded Neil Allen for Keith Hernandez. Coupled with the debut of Strawberry a month earlier the Mets had arguably the two best position players they had ever had.
     
    Cashen’s biggest decision for 1984 was the hiring of new manager — Davey Johnson, who Cashen knew from his Oriole days. Johnson had managed in the system, and like Cashen wanted to play the kids rather than continuing to lose with veterans. In 1984 the Mets finally broke through, winning 90 games after having won fewer than 70 for seven consecutive seasons. The biggest improvement on the club was the pitching, which featured three rookies: Ron Darling (acquired from Texas), Sid Fernandez (acquired from the Dodgers), and 19-year-old phenom Dwight Gooden.
     
    In the following off-season Cashen landed third baseman Howard Johnson and catcher Gary Carter in separate deals, and suddenly the Mets had one of the game’s best offenses to go with their great pitching. New York won 98 games and took the Cardinals down to the season’s final days before falling three games short. While Carter, Hernandez and Strawberry had good years, it was Gooden who had a season for the ages — 24-4, 1.53.
     
    After the 1985 season Cashen made another great trade, dealing unneeded players to the Red Sox for pitcher Bob Ojeda. The resultant Mets made a mockery out of the league in 1986, winning 108 games and waltzing to the division title, then survived two brutal playoff series to win their first title since 1969. It was an extremely well-balanced team, with the best offense and pitching in the league, and only one player accumulating 5 WAR (Hernandez). The club was filled with young stars and seemed poised to win several more championships.
     
    This did not happen, even with Cashen making two more great trades that winter, landing Kevin McReynolds and David Cone. Gooden entered drug rehab in April 1987, and it was Gooden’s problems more than any other that foretold the Mets’ decline. They remained a competitive team for several years, and won 100 games and the NL East in 1988, but were never again able to put it together as they had in 1986. Gooden and Strawberry, their two bright young stars, had good years remaining, but both had long battles with drugs and crime, likely costing Hall of Fame careers for both. Hernandez and Carter declined for more conventional reasons — aging, and the team appeared rudderless by 1990.
     
    Cashen let Davey Johnson go during another second place finish in 1990, and resigned himself after the 1991 squad finished fifth. He remained an advisor to the Mets for several years.
     
    Cashen’s front office record is extraordinary. He directed a great organization in Baltimore, and after taking over as GM, he made some great trades to keep the Orioles in contention and won two division titles in four years. In New York he inherited a mess, and used the Oriole model to build the organization — scouting, player development, and excellent young pitching. Although it ended sooner than he would have liked, the seven-year run (1984-1990) averaged 94 wins per season, finishing first or second every year, and captured a title. This was the most successful period ever for the club, on and off the field — coupled with a down period for the Yankees, the Mets were by far the most popular team in New York for several years, giving hope that they could be so once again with another great team.
     
    To read more about the history of baseball operations and the GM, please buy our new book In Pursuit of Pennants–Baseball Operations from Deadball to Moneyball via the publisher or at your favorite on-line store.
  2. Daniel R Levitt
    This post is part of a series in which Mark Armour and I count down the 25 best GMs in history, crossposting from our blog. For an explanation, please see this post.
     
    [This one is from Mark]
     
    There is an ongoing debate in Boston as to how to divvy up credit between Theo Epstein and Dan Duquette for the 2004 World Series title. Duquette ran the team through 2001, so of course many of the better players on the 2004 club joined the team on his watch. This is all true, but undersells the difficulty of turning a good team into a great team.
     
    Epstein became the general manager of the Red Sox in November 2002, after the team was spurned by Billy Beane. In fact, Beane’s strong recommendation of Epstein helped him get the job. Owner John Henry had made his fortune as a commodities trader, developing a system that took the emotional element out of trading decisions. To run his team he naturally wanted someone with an analytical mindset, someone who made decisions based on data and evidence.
     
    The 2002 Red Sox had won 93 games, and featured Pedro Martinez, Nomar Garciaparra, Manny Ramirez, Derek Lowe, Tim Wakefield, Johnny Damon, Jason Varitek and Trot Nixon. It was a great core, though the team also had obvious holes and they were competing against a team — the Yankees — who had won 103 games and seemed primed to continue doing so. To fill these holes, Epstein, like Beane, would rely on a modern understanding of how to value players, and how players were likely to develop.
     
    Epstein had a very busy and productive first few months, landing David Ortiz, Bill Muellar, Kevin Millar, Mike Timlin, Bronson Arroyo and Todd Walker in low-cost deals. Several incumbents regressed in 2003, but Epstein’s tremendous haul got them up to 95 wins and, ultimately, a devastating seventh game loss to the Yankees in the ALCS. Epstein went after bigger fish the next winter, and landed Curt Schilling, Keith Foulke, and Mark Belhorn, along with manager Terry Francona. This got them to 98 wins, and (after finally slaying the Yankees in an epic ALCS) their first World Series title in 86 years.
     
    After Epstein got the job he repeatedly said that he wanted to build a “$100 million player development machine” to provide (a) young talent for the Red Sox, ( depth to deal with injuries or poor performance, and © assets to deal to fill in holes. It all started with the amateur draft and young international free agents. The 2003-2004 teams had their success before Epstein’s machine had been built, but he did not lose sight of the future, the team he wanted to create.
     
    In the two off-seasons following their 2004 championship, the Red Sox lost several high-priced free agents, including Martinez, Lowe, and Damon, while cashing in the additional draft picks they received as compensation. Meanwhile, the organization was developing the next generation of stars. The Red Sox drafted Kevin Youkilis in 2001, Jon Lester in 2002, Jonathan Papelbon in 2003, Dustin Pedroia in 2004, and Clay Buchholz and Jacoby Ellsbury in 2005 — extraordinary production, and all of them were largely developed in Epstein’s system. By 2007 all six had reached the big leagues and, along with a few trade acquisitions and free-agent signings, helped the Red Sox win another World Series. As sweet as the first title was, it was the second that validated Epstein’s approach.
     
    The Red Sox won 95 games in both 2008 (resulting in an oh-so-close seven-game ALCS loss to the Rays) and 2009 (a first round sweep to the Angels). The latter playoff exit, coupled with the hated Yankees World Series triumph, made Epstein conclude that it was time to wait for the next team to develop. Although he believed the team could continue to compete with a few low-cost patches, “we all don’t want to sacrifice our competitiveness during the bridge just for the future. So we’re just trying to balance both those issues.” These comments were skewered in the press (“It’s nice that Theo has a passion for player development,” wrote Dan Shaughnessy in the Globe, “but asking fans to take a year off is outrageous. Henry is a billionaire and the Sox are making bundles of money.”) At least partly as a result of the backlash from fans and the media, Epstein’s bosses told him to double down and spend more money.
     
    Within a few weeks the Red Sox signed John Lackey, Adrian Beltre, Mike Cameron, and Marco Scutaro. After the Red Sox, with the second-highest payroll in baseball, failed to make the postseason in 2010, the team opened the vault even more, signing Carl Crawford (seven years, $142 million) and trading for Adrian Gonzalez and extending his contract (seven years, $154 million). Several of the signings cost the team draft choices, and the Gonzalez deal cost them three of the best players in their system.
     
    The Red Sox were hailed as a super-team heading into the 2011 season, and they played like it for five months. At the end of August they had an 83-52 record, the best record in the American League. Thanks mainly to dreadful pitching, they crashed to 7-20 in September, losing the division race and, on the final day of the season, the wild card as well. After this stunning collapse and multiple stories concerning turmoil in the clubhouse, Francona, sensing ownership had lost faith in him, resigned. A couple of weeks later Epstein followed suit, taking a job with the Cubs as President of Baseball Operations.
     
    “It was my fault,” Epstein lamented later. “I ****ed up by giving in to [the trades and signings]. I think [baseball ops] was really good at being true to our approach in the early and middle years, then toward the end—and I blame myself for this—we sort of gave in to it.”
     
    With the Cubs Epstein has a better title and more rope but essentially the same job. He hired Jed Hoyer as the GM, but in reality Hoyer fills a role much like a traditional assistant GM. A modern baseball ops group has a lot to do and requires much broader array of talent than it did a generation ago. If things go well a lot of people will deserve and receive credit for it.
     
    Importantly, Epstein resolved to build his machine and fight for it. Unlike in Boston, he took over a team with little talent so his patient approach offered little immediate relief for the faithful — the club finished 61-101, 66-96, and 73-89 his first three years.
     
    But there is hope. We hate to get ahead of the story here, but Epstein appears to have executed the first part of his plan wonderfully. There is a lot of young or mid-career talent and the farm system is loaded. Epstein signed Jon Lester, and traded for catcher Miguel Montero and outfielder Dexter Fowler, suggesting he feels the team is getting close. The team could contend for the post-season this year, and will be expected to do so starting in 2016. If Epstein pulls this off, if he wins in Chicago after winning in Boston, he will deserve a much higher ranking than this, well into the top ten and talk of Cooperstown. But for now we will leave him here, and follow along with the rest of you.
     
    To read more about the history of baseball operations and the GM, please buy our new book In Pursuit of Pennants–Baseball Operations from Deadball to Moneyball via the publisher or at your favorite on-line store.
  3. Daniel R Levitt
    This post is part of a series in which Mark Armour and I count down the 25 best GMs in history, crossposting from our blog. For an explanation, please see this post.
     
    [This one is from Mark]

    Lee MacPhail ran two baseball teams — the Orioles (1958-1965) and Yankees (1966-1973) — and did not win a pennant at either stop. That said, the evidence suggests that he did a great job at both places, dramatically improving organizations that had been in disarray and won championships soon after he had (voluntarily) moved on. MacPhail spent more than four decades in the game and is perhaps best known today for his tenure as AL president, but his role as a builder of teams should not be forgotten.
     
    The son of a brilliant but combative Hall of Fame baseball executive, Lee MacPhail inherited his father’s intelligence but not his personality. While Larry had a short and somewhat mercurial baseball career colored by occasional triumph and continual controversy, Lee quietly earned the respect and admiration of nearly everyone he met. Lee spent a few years running minor league teams in the Dodger and Yankee organizations, before serving several years as George Weiss’s chief assistant with the Yankees, responsible for one of the most productive farm systems in the game. In late 1958 MacPhail became the general manager of the Baltimore Orioles.
     
    Paul Richards had been serving as both GM and manager in Baltimore, but ownership had tired of his excessive bonuses to players who did not pan out, and the destructive disharmony between Richards and farm director Jim McLaughlin. The hiring of MacPhail (who kept Richards as manager) lessened the bonuses and led to a general calming of the organization. After another sixth place finish in 1959, the club broke through with an 89-65 record and a second place finish in 1960. A solid group of players from their system – Brooks Robinson, Ron Hansen, Jerry Adair, Milt Pappas, Steve Barber, Chuck Estrada and others – made up a youthful core.
     
    By 1961, both McLaughlin and Richards were gone, and MacPhail promoted Harry Dalton to run the farm system. Dalton formalized the organizational instruction and what became known as the Oriole Way, and the MacPhail/Dalton organization was soon a model in the game. In a five-year period beginning in 1959, the Orioles signed Boog Powell, Dave McNally, Jim Palmer, Mark Belanger, Dave Johnson, Dean Chance, Tom Phoebus, and Andy Etchebarren, along with several other future major leaguers. MacPhail also proved adept at nabbing useful players from other organizations, like Jim Gentile from the Dodgers in 1959, Jackie Brandt from the Giants in 1959, relief pitcher Stu Miller from the Giants in 1962, and pitcher Robin Roberts (who had been released by the Yankees) also in 1962. In early 1963 he acquired Luis Aparicio from the White Sox for four good players: infielders Ron Hansen and Pete Ward, outfielder Dave Nicholson, and veteran relief ace Hoyt Wilhelm. The cost proved to be steep, but Aparicio provided outstanding defense and base running for several years in Baltimore. The 1964 club, with Powell, Aparicio, and Robinson (league MVP) having big years and Steve Barber, Milt Pappas and Wally Bunker anchoring a fine pitching staff, won 97 games, finishing just two games back of the Yankees for the AL pennant. They won 94 more in 1965.
     
    After the 1965 season baseball hired a new commissioner, retired Air Force General William Eckert, a man who knew little about how the baseball business worked. To help ease his transition, the owners enticed MacPhail to accept a new job as Eckert’s assistant. As his last act as the Orioles GM, MacPhail attended the 1965 winter meetings and held talks with Cincinnati on a deal to bring star outfielder Frank Robinson to Baltimore, leaving final approval to his successor, Dalton. The new GM agreed, and the Orioles went on to win the 1966 World Series and become the winningest team in baseball over the next two decades. After the 1966 season MacPhail was named the Sporting News Executive of the Year, in recognition of his building of the Orioles and his year hand-holding the commissioner.
     
    MacPhail’s next job was back with the Yankees, who named him their general manager in October 1966. The club had been purchased by CBS in 1964, and fell to sixth place and then tenth (last) place. In response, CBS named Mike Burke club president, and Burke talked MacPhail into running the baseball team. Burke focused on promoting the team (which had become very unpopular), selling tickets, and Yankee Stadium itself. For the most part, Burke left MacPhail alone to run baseball operations, and the latter got to work. Within a few months he traded Roger Maris, Clete Boyer, and Pedro Ramos; within a few years nearly all of the 1964 champions were gone. Whitey Ford and Mickey Mantle were allowed to retire as Yankees, but the rest were sent packing in favor of younger players.
     
    Little by little, talented players began to arrive. Mel Stottlemyre was the one youngster from the 1964 team that lasted into the 1970s, providing the team a decade of solid pitching. Outfielder Roy White debuted in 1965 and took a couple of years to begin to hit, but by 1968 he was an underrated star. Left-handed pitcher Fritz Peterson came up in 1966, Stan Bahnsen won 17 games and the Rookie of the Year Award in 1968, Bobby Murcer joined the lineup in 1969, and Thurman Munson in 1970. After another rough year in 1967, the Yankees won 83 games in 1968, then 93 in 1970. Although MacPhail’s conservative approach to rebuilding the team (before the quicker fix of free agency) required time and patience, he thought it was close to paying off.
     
    MacPhail made his best two deals in 1972, acquiring relief pitcher Sparky Lyle from Boston just before the season, and third baseman Graig Nettles just after. The Yankees were in their first division race in eight years that September, before falling short in a tight four-team battle. With Lyle and Nettles added to Stottlemyre, Peterson, White, Munson, and Murcer, many observers considered the Yankees one of baseball’s best teams heading into 1973. Before the season started, CBS sold the club to a group led by Cleveland shipbuilder George Steinbrenner, the man destined to be the dominant force in the front office for the next 35 years. Burke resigned a few months later, and MacPhail followed at the end of the season. The Yankees were in first place much of the summer, but a brutal August left them far behind the Orioles.
     
    MacPhail did not win in New York, but he improved the organization considerably in his seven years in charge, and left a lot of talent for Steinbrenner and new GM Gabe Paul. During the years between the start of the amateur draft (1965) and the advent of free agency (1976) the Yankees could not rely on money or prestige. Building the team took patience, and the Yankees were vastly improved from the 10th place club MacPhail and Burke inherited.
     
    MacPhail spent ten years as AL president, then two more as the owners’ chief negotiator with the player’s union. He finally retired in 1985, ending an impressive career in the game. His two stints as general manager deserve their due.

    To read more about the history of baseball operations and the GM, please buy our new book In Pursuit of Pennants–Baseball Operations from Deadball to Moneyball via the publisher or at your favorite on-line store.
  4. Daniel R Levitt
    This post is part of a series in which Mark Armour and I count down the 25 best GMs in history, crossposting from our blog. For an explanation, please see this post.
     
    For the 32 seasons before John Hart was promoted to general manager in September 1991, the Cleveland Indians never finished closer than 11 games from first in a full season. And they certainly didn’t appear to be making progress; in 1991 the team lost 105 games, finished last in the league in runs and ninth in runs allowed, and drew the fewest fans in the league for the third year in row. Hart had his work cut out for him.
     
    Cleveland had brought Hart to the big leagues after several years managing in the Orioles minor league system. When the Indians fired manager Doc Edwards late in the 1989 season, the team named Hart, then the third base coach, to finish out the final 19 games. Hart moved to the front office after the season, working closely with GM Hank Peters, and was instrumental in acquiring Carlos Baerga.
     
    Hart got the top job two years later, and made the most of the talent he inherited. He smartly recognized that Albert Belle, Jim Thome, Manny Ramirez, Charles Nagy, Sandy Alomar and Baerga could form the basis of a pretty good team, and held on to all of them. He bolstered his nucleus with some great trades, picking up Kenny Lofton, Omar Vizquel, Paul Sorrento, and Jose Mesa, and veteran free agent signings, including Eddie Murray, Dennis Martinez, and Orel Hershiser.
     
    The team began making steady progress, winning 76 games Hart’s first two years. In the strike shortened 1994 season the Indians were in second place at 66-47 when the season ended. The next year they romped through the regular season, finishing 100-44, at .694 the fourth highest winning percentage of any team since World War II. The Indians won their first two playoff series and the pennant before dropping a close six game World Series to the Braves, three losses coming by only one run. Hart was recognized for his efforts by winning the Sporting News Executive of the Year Award in both 1994 and 1995.
     
    As Hart’s team was jelling in the early 1990s, he considered ways to bring some payroll stability and predictability to the team’s finances. Salaries were escalating dramatically through both arbitration and free agency. Hart crafted a strategy to approach his young players years in advance of free agency and offer long term contract extensions to buy out the uncertainty of future salary increases. Hart first offered such deals to Baerga and Alomar, both represented by high-profile agent Scott Boras. The agent advised against the extensions, but both players chose to sign. With these two young leaders in the fold, Hart successfully did the same with Belle, Lofton, and Nagy. This strategy has gained adherents over the years, and it is now common to see teams, particularly those in smaller markets, negotiate long term extensions with players who were already under the team’s control for several more years.
     
    Hart gained another advantage a few years into his tenure. A new ballpark, now known as Progressive Field, opened in 1994 to critical and popular acclaim. The team soon began a streak of 455 straight sellouts and jumped to second in the league in attendance. The new revenues allowed Hart the freedom to chase higher priced free agents and he generally spent his money well.
     
    From 1995 through 2001, the Indians claimed six of seven division titles, making it back to the World Series in 1997, when they lost a heartbreaking Game Seven to the Marlins. To sustain the team’s competitiveness Hart continued to make some solid moves, adding David Justice and Marquis Grissom by trade, Roberto Alomar as a free agent, and Bartolo Colon, an amateur free agent signing from the Dominican Republic.
     
    Less successfully, Hart used many of his best prospects in an attempt to plug holes by trading for veterans. In these years Hart dealt such players as Sean Casey, Danny Graves, Jeromy Burnitz, Brian Giles, and Richie Sexon, often in order to acquire a veteran player who proved less productive than the player he gave up. A comparison to the Atlanta Braves of the same period is instructive. The 1994 Braves were the best team in baseball and handed starting jobs to two rookies: Ryan Klesko and Javy Lopez. Within a couple of years, Chipper and Andruw Jones also claimed key roles on the team. This on-the-fly rebuild allowed Atlanta continued success into the 2000s, whereas the Indians fell back.
     
    At the end of the 2001 season, after an extraordinary decade in charge, Hart resigned, and planned to take a year off to recharge his batteries. But when Texas owner Tom Hicks offered Hart a three-year contract at $2 million per year, possibly making him the highest priced GM in the game, he accepted the new challenge. Hicks had lavished the largest contract in baseball history on Alex Rodriguez the previous season only to finish 73-89. Hart believed the team was closer to contention than it appeared and signed free agents Chan Ho Park and Juan Gonzalez to expensive contracts. Both players nosedived, and the team again struggled.
     
    Hart recommitted the team to the younger players and the farm system, but success remained elusive, and in 2003, despite the success of youngsters Mark Teixeira, Michael Young and Hank Blaylock, the team continued to tread water. Moreover, Hicks’s investment firm was running into financial difficulties, boosting the appeal of a younger, cheaper team. After the season Hart swapped Alex Rodriguez for Alfonso Soriano to free up payroll. The team jumped to 89 wins in 2004 but still missed the playoffs. The gains were fleeting, however, and in 2005 the team fell back to 79 wins with a payroll that had dropped to ninth in the league from second in 2003. Hicks and Hart agreed after the season that the GM would step down, signing a long agreement to keep him with the Rangers as a senior advisor.
     
    Somewhat unexpectedly, Hart will get another shot at team building. In November 2013 Atlanta president John Schuerholz hired Hart, a close friend, as a senior advisor for the Braves. Like the Indians many years before, the Braves intended to lock a couple of their young stars up to long term contracts. Soon after Schuerholz dismissed Frank Wren late in the 2014 season, he and Hart agreed the latter would become president of baseball operations and assume the general manager’s duties.
     
    Mark Shapiro, his successor in Cleveland, once said, “One of John’s greatest attributes in Cleveland was his own personal gut feeling for talent evaluation.” It will be interesting to see how Hart does in the more corporate, dynamic, and complex front office world of 2015. He was one of the best in the game during his Cleveland years, and Braves fans are hoping that he can recapture some of that magic.
     
    To read more about the history of baseball operations and the GM, please buy our new book In Pursuit of Pennants–Baseball Operations from Deadball to Moneyball via the publisher or at your favorite on-line store.
  5. Daniel R Levitt
    #25 — Andy MacPhail
     
    This post is part of a series in which Mark Armour and I count down the 25 best GMs in history, crossposting from our blog. For an explanation, please see this post.
     
    Andy MacPhail had big shoes to fill. Both his father Lee and his grandfather Larry are in the Hall of Fame as baseball executives. When the Minnesota Twins promoted the 33-year-old MacPhail to run the club, they surely took his pedigree into account. He lived up to his surname, and his surprisingly quick success cemented a wave of extremely young GMs, a couple with similar front office bloodlines.
     
    Coming out of college in 1976 MacPhail knew he wanted a career in a baseball front office and thought he had lined up a position with the Montreal Expos. Unfortunately, when the American League awarded an expansion franchise to Toronto that spring, creating a second major league team in Canada, the Expos were so dismayed with American League president Lee MacPhail that they rescinded the employment offer to Lee’s son. Andy quickly rebounded, taking a positon with the Cubs in park operations and player development. In early 1982, just 28, he joined Houston as assistant to general manager Al Rosen.
     
    New Minnesota Twins owner Carl Pohlad brought in MacPhail as vice president of player personnel in 1985 and one year later made him general manager, at 33 the youngest GM in baseball. The Twins had been mired in mediocrity or worse for the previous decade and a half; nevertheless the squad MacPhail took over had a number of talented young homegrown players, including Kirby Puckett, Kent Hrbek, Gary Gaetti, and Frank Viola.
     
    MacPhail made several moves to bolster his nucleus with veteran talent, trading for left fielder Dan Gladden and closer Jeff Reardon and signing reliever Juan Berenguer. The 1987 Twins crept up to 85 wins, but it was enough to win a weak AL West and beat the Tigers in the ALCS. When the Twins defeated the Cardinals in the 1987 World Series, everyone associated with the team became a regional hero, perhaps because other than the Minneapolis Lakers in the late 1940s and early 1950s (before the NBA was popularly established as a national league), no Minnesota professional team had won a championship in any of the four major sports. MacPhail was hailed as “Boy Wonder.”
     
    Despite his quick success, MacPhail recognized that lower revenue teams could only compete cyclically and that a team needed a solid crop of low-salaried youngsters and under-appreciated veterans who could ripen concurrently, leaving some payroll available to plug holes with free agents. Sensing the team was not ready to compete for a title, in 1989 MacPhail traded Viola, the previous year’s Cy Young Award Winner, for several players, most notably pitchers Rick Aguilera and Kevin Tapani. The Twins fell to last place in 1990, but MacPhail felt his restructured team had enough talent and some payroll flexibility.
     
    Before the 1991 season he signed free agents Mike Pagliarulo, Jack Morris, and Chili Davis, while farm products Chuck Knoblauch and Scott Erickson came through with star-quality seasons. The team won 95 games, going from last to first in their division, and again prevailed in a seven game World Series. More than two decades later, these two Twins World Series victories remain Minnesota’s only substantive men’s professional sports championships. During his stint in Minnesota MacPhail was brilliant at managing his payroll, recognizing when he had a team close to contention, and using his payroll capacity to acquire in the right veterans.
     
    MacPhail’s success helped usher in a new era of very young GMs. Oakland had hired Sandy Alderson in 1983, and Texas had brought in Tom Grieve a year later—both just 35—but after MacPhail the minimum age fell even further. Dave Dombrowski and Jim Bowden were only 31 and Randy Smith just 29 when hired. Smith and Bill Bavasi, just 36 when he became a GM, were like MacPhail scions of successful front office executives. Somewhat surprisingly, other than by Alderson, the analytic revolution that was slowly seeping into baseball before Moneyball was not really embraced by this generation of young GMs.
     
    The Twins remained competitive in 1992, but fell off quickly thereafter as several players left as free agents, the pitching deteriorated, and several younger players performed below expectations. With rapidly increasing salaries throughout baseball after an arbitrator ruled the owners had been colluding to keep salaries down, MacPhail was becoming increasingly pessimistic on the future of small market clubs. “I can’t make it work anymore,” MacPhail said regarding even his successful cyclic approach to building a competitive team.
     
    After a players strike shut down the final phase of the 1994 baseball season, the Tribune Company hired MacPhail to be president and CEO of the Cubs, one of baseball’s most venerable but long-suffering teams. As his title implied, MacPhail was responsible for the entire franchise and named Ed Lynch his general manager. MacPhail intended to build a “development-based” organization while at the same time bringing in veterans to keep Chicago competitive in a weak division.
     
    In mid-2000, after just one playoff appearance in five years, MacPhail jettisoned Lynch and assumed the GM duties himself. He got the club up to 88 wins in 2001, but the next July MacPhail named Jim Hendry the GM. In 2003 the Cubs won 88 games and qualified for the playoffs, where the team advanced to the NLCS, before losing a heartbreaking seven game series to the Marlins. The Cubs would not make the post season again under MacPhail’s reign, and he resigned after a disappointing 66-96 record in 2006. Certainly the Cubs suffered some bad luck—phenom pitchers Kerry Wood and Mark Prior pitched 200 or more innings only three times between them due to injuries–but the farm system did not deliver as expected and several prospects were traded away with little substantive return. In contrast, MacPhail was highly successful in the off-field part of his job, as attendance and revenues surged during his 12 years at the helm.
     
    MacPhail was not unemployed for long; in mid-2007 Orioles owner Peter Angelos brought him aboard as president of baseball operations, acting as a general manager with considerable authority. Baltimore had fallen on hard times since consecutive ALCS trips in the late 1990s, winning fewer than 80 games every year from 1998 to 2007, but MacPhail again hoped to create a “top echelon scouting and development franchise.” When the farm system appeared to be more efficient at developing pitching, MacPhail’s strategy evolved to “buy the bats and grow the arms.”
     
    Unfortunately, many of the young hurlers never progressed as hoped, and the Orioles lost over 90 games every season through 2011, after which MacPhail resigned. The next year Baltimore was baseball’s surprise team; they won 93 games and made the playoffs, mostly with a team built by MacPhail. Although he wasn’t around to enjoy it, MacPhail’s farm system and savvy trades for the likes of Adam Jones, Mark Reynolds, J.J. Hardy, and Chris Davis left the Orioles with a solid talent base.
     
    To read more about the history of baseball operations and the GM, please buy our new book In Pursuit of Pennants–Baseball Operations from Deadball to Moneyball via the publisher or at your favorite on-line store.
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