Baseball 101: Wheeling and dealing

A composite of some of the players involved in baseball's biggest trades as ranked by Mark Herrmann for Newsday's 2019 edition of "Baseball 101." Credit: AP Photos; Getty Images; Newsday

Let’s make a deal.”

That isn’t a baseball epigram, per se, but in spirit it is as essential to the sport as “Play ball!” Moving players from one team to another, in exchange for other players or for money or other surprising commodities, is as much a part of the game as seams on the ball.

With that in mind, our 2019 edition of Baseball 101 is all about trades. We present this listing — not a ranking after our selection for No. 1, but a listing — of 101 deals to remember or forget, depending on your point of view:

1. Babe Ruth, Red Sox, to Yankees for cash, 1919.

No, no, it wasn’t “No, No, Nanette.” Contrary to the story that has circulated for nearly a century, the pivotal figure in baseball history was not sold because Red Sox owner Harry Frazee, a theatrical producer, needed funding for the musical. The show did not open on Broadway until 1925, two years after Frazee had sold the team.

Other factors produced what a Baseball Hall of Fame publication calls “The Deal that Changed the Game.” An article published in 2008 by the Society of American Baseball Research said Frazee was under pressure to repay Joseph Lannin, from whom he had bought the team. Authors Glenn Stout and Richard Johnson, in a 2000 book titled “Red Sox Century,” said Frazee was disliked by American League president Ban Johnson, who was doing all he could to make life difficult for the Sox (a contention disputed by SABR authors Daniel R. Levitt, Mark Armour and Matthew Levitt).

There is no disputing the crystal clarity of the deal’s result. It catapulted the Yankees toward being American sports’ greatest dynasty for more than 40 years, and it sent the Red Sox reeling under what was called a “Curse” until they finally won the World Series in 2004.

Ruth already was baseball’s biggest star in 1919, having just broken a 35-year-old single-season home run record with 29 (his later record of 60 in 1927 would last 34 years). But he was displeased with his $10,000 Red Sox salary and considered a thorn in the team’s side. The transaction was struck on Dec. 26, 1919, while Ruth was playing golf in Los Angeles: $100,000 cash in four installments and a $300,000 loan secured with the mortgage on Fenway Park. It was not announced until Jan. 5, giving Yankees manager Miller Huggins time to reach the West Coast and coax Ruth into agreeing.

The Boston Red Sox sold Babe Ruth to the Yankees 1919 in a deal that changed the course of both franchises for more than 80 years.

The deal became a landmark and template, explaining why teams still seek stars, why players feel justified in asking for all they can get and why the Red Sox have won four World Series in the past 15 seasons after having become big spenders.

“For each dollar they spent on Ruth, they made back twenty,” said economist Michael Haupert in “The Big Fella,” Jane Leavy’s current best-selling Ruth biography.

Haupert studied the Ruth-era accounting books, which are preserved at the Hall of Fame, and was amazed at what a windfall the Ruth purchase was, off the field as well as on it.

In that way, that one deal has influenced countless others, including many of the following 100:

2. Roger Maris, Athletics, with Joe DeMaestri, Kent Hadley to Yankees for Don Larsen, Hank Bauer, Norm Siebern and Marv Throneberry, 1959. Critics used to say the Yankees made so many one-sided deals with Kansas City that the Athletics were essentially a farm club for the Bronx team. Whether or not that was the case, the Yankees won this deal by a landslide. Maris won the Most Valuable Player Award in 1960 and made baseball history in 1961 by breaking Babe Ruth’s hallowed single-season home run record. Throneberry later became a New York institution in his own right, symbolizing the woeful early Mets after being acquired for their first expansion draft pick, Hobie Landrith.

3. Nolan Ryan, Mets, with Frank Estrada, Don Rose and Leroy Stanton to Angels for Jim Fregosi, 1971. Often forgotten is that the Mets had to include three other players to get the Angels to take Ryan, who would become the all-time strikeout leader and one of the most dominant pitchers in history (seven career no-hitters). Also forgotten is that this was the aftermath of a previous Mets gaffe, dealing Amos Otis for Joe Foy. The latter bombed out, so the team still was shopping for a third baseman.

Mike Piazza in his first at-bat for the Florida Marlins...

Mike Piazza in his first at-bat for the Florida Marlins on May 16, 1998. Credit: AP/Leon Algee

4. Mike Piazza, Marlins, to Mets for Preston Wilson, Ed Yarnall and Geoff Goetz, 1998. Piazza’s second major trade in eight days, which followed the megadeal from the Dodgers, changed the trajectory of the Mets’ franchise. They were in the playoffs the next year and the World Series the year after that, and Piazza was on his way to Cooperstown with a Mets cap on his plaque.

5. Frank Robinson, Reds, to Orioles for Milt Pappas, Jack Baldschun, Dick Simpson, 1965. Deemed by the Reds to be past his prime at 30, Frank Robinson turned this into one of the most lopsided trades in history. In his first season in Baltimore, he won the Triple Crown, was the American League Most Valuable Player and led the Orioles to the championship. He also played 10 more years.

6. Jose Cardenal, Phillies, to Mets for cash, 1979. Deal took place between games of a doubleheader between the teams. After switching clubhouses at Shea Stadium, Cardenal told his new manager, Joe Torre, that he was too shocked to start the second game.

7. Max Flack, Cubs, to Cardinals for Cliff Heathcote, 1922. Also between games of a doubleheader. Unlike Cardenal, each got a hit for his new team in the nightcap.

8. Fred Lynn, Orioles, to Tigers for Chris Hoiles, Cesar Mejia, Robinson Garces, 1988. Lynn originally was ruled ineligible for the postseason because he did not report to his new team before midnight Aug. 31 (his charter flight was delayed 10 minutes). The decision was reversed.

9. Justin Verlander, Tigers, and Juan Ramirez to Astros for Daz Cameron, Franklin Perez, Jake Rogers, 2017. Verlander agreed about two minutes before the deadline, then led Astros to their first title.

10. Paul O’Neill, Reds, with Joe DeBerry to Yankees for Roberto Kelly, 1992. O’Neill won the 1994 batting title and four World Series rings.

Texas Rangers shortstop Alex Rodriguez on July 17, 2000.

Texas Rangers shortstop Alex Rodriguez on July 17, 2000. Credit: AP/Al Messerschmidt Archive

11. Alex Rodriguez, Rangers, and cash to Yankees for Alfonso Soriano, Joaquin Arias, 2004. A-Rod appeared headed to the Red Sox, but the Players Association was skittish about the pay cut. Instead, he had 13 eventful years in New York, including one in which he was suspended.

12. Giancarlo Stanton, Marlins, to Yankees for Starlin Castro, Jose Devers, Jorge Guzman, 2017. Coming off a 59-homer, 132-RBI MVP season, Giancarlo Stanton was too expensive for new executive Derek Jeter.

13. Christian Yelich, Marlins, to Brewers for Lewis Brinson, Isan Diaz, Monte Harrison, Jordan Yamamoto, 2018. Spelled “t-a-n-k” for Jeter’s fire-sale team, spelled “M-V-P” in Milwaukee.

14. Sparky Lyle, Red Sox, to Yankees for Danny Cater, 1972. Lyle transformed the Yankees’ atmosphere and performance. Won the Cy Young Award and a World Series ring in 1977, two years after Cater was out of baseball.

15. Lou Brock, Cubs, with Jack Spring and Paul Toth to Cardinals for Ernie Broglio, Doug Clemens, Bobby Shantz, 1964. Brock played in three World Series (won two), set the steals record and reached the Hall of Fame.

16. David Cone, Royals, with Chris Jelic to Mets for Ed Hearn, Rick Anderson, Mauro Gozzo, 1987. Advantage, Mets.

17. David Cone, Mets, to Blue Jays for Jeff Kent, Ryan Thompson, 1992. Kent was a borderline Hall of Famer, but not with Mets.

18. David Cone, Blue Jays, to Yankees for Marty Janzen, Mike Gordon, Jason Jarvis, 1995. A perfect game and four titles later, advantage, Yankees.

David Cone won four World Series with the Yankees and one with the Blue Jays.

19. Max Scherzer, Diamondbacks, to Tigers in three-team trade with Yankees, 2009. Ian Kennedy went to the Diamondbacks, Curtis Granderson to the Yankees, Scherzer to stardom.

20. Jesse Orosco, Twins, with Greg Field to Mets for Jerry Koosman, 1979. The only two pitchers to finish a World Series-clinching game for the Mets were traded for each other.

21. Doyle Alexander, Braves, to Tigers for John Smoltz, 1987. Alexander went 9-0 down the stretch, helping Detroit win the division. Smoltz, struggling with a 5.68 ERA in Double-A at the time of the deal, went to the Hall of Fame.

22. Jay Buhner, Yankees, with Rick Balabon and Troy Evers, to Mariners for Ken Phelps, 1988. Immortalized by the Seinfeld episode in which the George Steinbrenner character (mistakenly) tells the Costanzas their son George is dead. The first thing Frank Costanza says is “What the hell did you trade Jay Buhner for?”

23. Joel Youngblood, Mets, to Expos for Tom Gorman, 1982. Youngblood played an afternoon game in Chicago, flew to Philadelphia and played that night. He had a hit in each game.

24. Harry Chiti, Indians, to Mets for Harry Chiti, 1962. Mets acquired him for a player to be named, saw little production and sent him back. Technically listed as a purchase each way.

25. John McDonald, Blue Jays, to Tigers for John McDonald, 2005. Similarly, he was the player to be named, four months later.

26. Dave Winfield, Twins, to Indians for a dinner, 1994. Teams agreed on the deal during the strike but never could agree on compensation. The Indians reportedly settled it by taking the Twins’ front office out for a fancy meal.

27. Gil Hodges, Senators manager, to Mets for Bill Denehy and cash, 1967. Washington demanded something in return and sought the reliever. In 1969, Hodges orchestrated a Miracle, which possibly inspired the following manager-player deals:

28. Chuck Tanner, Athletics manager, to Pirates for Manny Sanguillen and cash, 1976.

29. Lou Piniella, Mariners manager, with Antonio Perez to Rays for Randy Winn, 2002.

30. Ozzie Guillen, White Sox manager, with Ricardo Andres to Marlins for Jhan Marinez and Ozzie Martinez, 2011.

31. John Farrell, Blue Jays manager, with David Carpenter to Red Sox for Mike Aviles, 2012.

32. Jimmy Dykes, Tigers manager, for Indians manager Joe Gordon, 1960. Only time two managers were dealt for each other. Clubs finished a combined 47 games behind the Yankees.

33. Jackie Robinson, Dodgers, to Giants for Dick Littlefield and cash, 1956. Robinson retired rather than report to the rival.

Willie Mays at Shea Stadium in 1972.

Willie Mays at Shea Stadium in 1972. Credit: AP

34. Willie Mays, Giants, to Mets for Charlie Williams and cash, 1972. Icon’s sentimental journey back to the city in which he began. Wound up in 1973 World Series.

35. Clete Boyer, Yankees, to Braves for Bill Robinson, Chi-Chi Olivo, 1966. Boyer hit career-high 26 home runs in 1967 and won his only Gold Glove in 1969.

36. Art Ditmar, Bobby Shantz, Clete Boyer, Curt Roberts, Wayne Belardi, Jack McMahan, Athletics, to Yankees for Billy Hunter, Tom Morgan, Irv Noren, Rip Coleman, Milt Graff, Mickey McDermott, Jack Urban, 1957. Multi-player, one-sided.

37. Ken Boyer, Cardinals, to Mets for Charley Smith, Al Jackson, 1965. For two seasons, each New York team had a Boyer brother at third base.

38. Charley Smith, Cardinals, to Yankees for Roger Maris, 1966. Maris helped the Cardinals win two pennants and a World Series. Smith batted .224 in one season as a Yankee.

39. Lee Mazzilli, Mets, to Rangers for Ron Darling, Walt Terrell, 1982. Mazzilli, a fan darling (small “d”), was reacquired and became Darling’s teammate on the champion 1986 Mets.

40. Lee Mazzilli, Rangers, to Yankees for Bucky Dent, 1982. Only four years after Dent hit the homer.

41. Rusty Staub, Astros, to Expos for Jesus Alou and Donn Clendenon, 1969. Clendenon refused to report, so the Expos substituted Jack Billingham, Skip Guinn and cash. Led to . . .

42. Donn Clendenon, Expos, to Mets for Steve Renko, Kevin Collins, Jay Cardon, David Colon, Terry Dailey, 1969. June 15 deal helped create the Miracle. Clendenon was World Series MVP.

43. Rusty Staub, Expos, to Mets for Ken Singleton, Tim Foli, Mike Jorgensen, 1972. Staub later was dealt to Detroit for Mickey Lolich but remained a New Yorker for the rest of his life.

44. Hank Aaron, Braves, to Brewers for Dave May and Roger Alexander, 1974. Aaron hit the final 22 of his then-record 755 home runs after his return to Milwaukee, where he played with the Braves from 1954-65.

Milwaukee Brewers' outfielder Hank Aaron is seen in 1975.

Milwaukee Brewers' outfielder Hank Aaron is seen in 1975. Credit: AP

45. Eddie Mathews, Braves, with Sandy Alomar and Arnold Umbach to Astros for Bob Bruce and Dave Nicholson, 1966. Mathews played 15 years for the Braves in three cities: Boston, Milwaukee, Atlanta.

46. Joe Morgan, Astros, with Jack Billingham, Cesar Geronimo, Denis Menke, Ed Armbrister to Reds for Lee May, Tommy Helms, Jimmy Stewart, 1971. In Cincinnati, Morgan was an eight-time All-Star, two-time MVP, two-time world champion before returning to Houston in 1980 as a free agent.

47. Dixie Walker, Dodgers, with Vic Lombardi and Hal Gregg to Pirates for Preacher Roe, Billy Cox, Gene Mauch, 1947. Walker reportedly didn’t want to play alongside Jackie Robinson.

48. Anthony Rizzo, Padres, with Zach Cates to Cubs for Andrew Cashner, Kyung-Min Na, 2012. Rizzo, slugger and Gold Glove first baseman, had been traded by the Red Sox, too.

49. Pedro Martinez, Dodgers, to Expos for Delino DeShields, 1993. At the time, Martinez had only three starts but was 10-6.

50. Pedro Martinez, Expos, to Red Sox for Tony Armas, Carl Pavano, 1997. And Martinez had just won the Cy Young Award.

51. Gary Carter, Expos, to Mets for Hubie Brooks, Mike Fitzgerald, Herm Winningham, Floyd Youmans, 1984. Brooks’ reaction: “Damn, I’ve got to face Dwight.”

The Expos' Gary Carter during spring training.

The Expos' Gary Carter during spring training. Credit: AP/Tom DiPace

52. Randy Johnson, Expos, with Gene Harris and Brian Holman to Mariners for Mark Langston and Mike Campbell, 1989. After only 11 games over two seasons, Montreal determined it had seen enough of the Big Unit.

53. Jimmie Foxx, Athletics, and Johnny Marcum to Red Sox for Gordon Rhodes, George Savino and cash, 1935. Foxx, a Hall of Famer who hit 58 homers in 1932, was the last member of the Philadelphia juggernaut dispatched by a franchise reeling from the Great Depression.

54. Joe Torre, Braves, to Cardinals for Orlando Cepeda, 1969. Cepeda never regained his MVP form of 1967. Torre was MVP in 1971.

55. Bobby Murcer, Yankees, to Giants for Bobby Bonds, 1974. Newsweek magazine wrote a story about it, headlined “Superswap.” Neither star lifted his new team. Murcer returned to the Yankees in 1979. Bonds helped the Yankees another way . . .

56. Bobby Bonds, Yankees, to Angels for Mickey Rivers, Ed Figueroa, 1975. First step toward three consecutive pennants.

57. Doc Medich, Yankees, to Pirates for Dock Ellis, Ken Brett, Willie Randolph, 1975. Randolph, a minor-leaguer, would be Yankees’ second baseman for 13 years.

58. John Olerud, Blue Jays, to Mets for Robert Person, 1996. Olerud provided a big boost toward playoff contention. Person went 8-13 with a 6.31 ERA in 2½ seasons for Toronto.

59. Ken Griffey Jr., Mariners, to Reds for Mike Cameron, Antonio Perez, Brett Tomko, Jake Meyer, 2000. Homecoming for kid from Cincinnati’s Moeller High.

60. Sal Maglie, Indians, to Dodgers for cash, 1956. “The Barber,” former standout for the Giants, would join the Yankees one year later and become the last to play for all three New York teams.

61. Joe Carter, Cubs, with Mel Hall, Don Schulze, Darryl Banks to Indians for Rick Sutcliffe, Ron Hassey, George Frazier, 1984. Deal jump-started Carter’s career but did more for the Cubs. Sutcliffe, the Cy Young Award winner, led them to the postseason for the first time since 1945.

62. Joe Carter and Roberto Alomar, Padres, to Blue Jays for Fred McGriff, Tony Fernandez, 1990. Four All-Stars. Alomar was a Hall of Famer, Carter ended the 1993 World Series with a three-run walk-off home run in Game 6.

63. Fred McGriff, Yankees, with Dave Collins, Mike Morgan and cash to Blue Jays for Dale Murray, Tom Dodd, 1982. Yanks reportedly got Murray to appease and ease the workload of Goose Gosssage.

64. Ozzie Smith, Padres, with Steve Mura, Al Olmstead to Cardinals for Garry Templeton, Sixto Lezcano, Luis DeLeon, 1981. Smith, known for taking the field with a backflip, would have done cartwheels had he known how this was going to work out.

65. Adrian Gonzalez, Josh Beckett, Carl Crawford, Nick Punto, Red Sox, to Dodgers for Ivan DeJesus, James Loney, Allen Webster, Jerry Sands, Rubby de la Rosa, 2012. $260 million in salaries, much of it being dumped by Boston.

66. Willie Hernandez, Phillies, with Dave Bergman to Tigers for Glenn Wilson, John Wockenfuss, 1984. In Hernandez, Tigers were looking for long relief help. They got the year’s MVP and Cy Young Award winner.

67. Joe DiMaggio, Yankees, for Ted Williams, Red Sox, 1947. Never actually happened but is said to have been seriously considered and is the most legendary non-trade ever.

Ted Williams of the Boston Red Sox on Aug. 18,...

Ted Williams of the Boston Red Sox on Aug. 18, 1942, with the Yankees' Joe DiMaggio. Credit: AP/ABE FOX

68. Rollie Fingers and Joe Rudi, Athletics, to Red Sox for cash, 1976. Voided by commissioner Bowie Kuhn, who cited “the best interests of baseball.”

69. Vida Blue, Athletics, to Yankees for cash, 1976. Ditto.

70. Curt Flood, Cardinals, with Tim McCarver, Joe Hoerner, Byron Browne to Phillies for Dick Allen, Cookie Rojas, Jerry Johnson, 1969. Flood refused to report and sued MLB over its reserve clause. He lost, but players ultimately won in 1975 as the clause was eliminated, opening the door to free agency.

71. Curt Flood, Phillies, with a player to be named to Senators for Greg Goossen, Gene Martin, Jeff Terpko, 1970. Terpko was the player to be named.

72. Keith Hernandez, Cardinals, to Mets for Neil Allen, Rick Ownbey, 1983. Hernandez was crestfallen about being sent to New York but 36 years later is, in some ways, still the face of the Mets’ franchise.

73. Jeff Bagwell, Red Sox, to Astros for Larry Andersen, 1990. Bagwell never played a major-league game for Boston, then 2,150 for Houston, ending up in Cooperstown.

74. George Foster, Giants, to Reds for Frank Duffy, Vern Geishert, 1971. Foster averaged 130 RBIs 1976-78. Giants dealt Duffy after he batted .179 in ’71.

75. Ryne Sandberg, Phillies, with Larry Bowa to Cubs for Ivan DeJesus, 1981. Sandberg had 13 career games for Phillies and 11 All-Star Games, nine Gold Gloves, seven Silver Sluggers, one MVP for Cubs.

76. Steve Carlton, Cardinals, to Phillies for Rick Wise, 1971. Carlton pitched to a 1.97 ERA and Cy Young Award in 1972 on his way to the Hall of Fame.

77. Tom Seaver, Mets, to Reds for Steve Henderson, Pat Zachry, Doug Flynn, Dan Norman, 1977. It took nearly a decade for the franchise to recover from trading The Franchise.

After being traded from the Mets, Tom Seaver went 113-81 (.582) in nine seasons. Pat Zachry was 41-46 (.471) in six seasons, Steve Henderson hit .287 with 35 homers in four seasons, Doug Flynn hit .234 and won a Gold Glove in five years and Dan Norman hit .230 in 282 at-bats over four seasons with the Mets.

78. Ten Yankees for seven Orioles, 1954. Biggest deal in terms of volume. Notables were pitchers Don Larsen and Bob Turley heading north. See baseball-reference.com for all the others.

79. Rickey Henderson, Athletics, with Bert Bradley to Yankees for Jose Rijo, Stan Javier, Eric Plunk, Tim Birtsas, Jay Howell, 1984. Plunk also was in the trade that brought Henderson back to Oakland in 1989.

80. Christy Mathewson, Reds, to Giants for Amos Rusie, 1900. “Big Six” had 373 wins, including 37 in 1908, for New York before returning and going 1-0 for Cincinnati in 1916.

81. Dennis Eckersley, Cubs, with Dan Rohn to Athletics for Brian Guinn, Mark Leonette, Dave Wilder, 1987. Oakland converted a pretty good starter into a dominant Hall of Fame closer.

82. Miguel Cabrera, Marlins, with Dontrelle Willis to Tigers for Andrew Miller, Cameron Maybin, Frankie De La Cruz, Burke Bradenhop, Mike Rabelo, 2007. In 2012, Cabrera was the first in 45 years to win Triple Crown.

83. Graig Nettles, Indians, with Jerry Moses to Yankees for Charlie Spikes, John Ellis, Jerry Kenney, Rusty Torres, 1972. Settled third base and helped set up Yankees’ resurgence in 1970s.

84. Nellie Fox, Athletics, to White Sox for Joe Tipton, 1949. Dramatically changed White Sox, who had six consecutive losing seasons. They finished at least eight games over .500 each of the next 13 seasons and won the 1959 American League pennant.

85. Cy Young, Canton (Independent League), to Cleveland Spiders (National League) for $300 and a new suit of clothes, 1890. If they were to name an award for best trade . . .

86. Kerry Ligtenberg, Minneapolis Loons (Independent League), to Braves for 12 dozen baseballs and two cases of bats, 1996. Loons manager Greg Olson, a former Brave, explained he needed equipment more than cash.

87. Early Wynn, Indians, with Al Smith to White Sox for Minnie Minoso, Fred Hatfield, 1957. Among many deals by Cleveland GM “Frantic Frank” Lane. Not one of his best. Wynn won the Cy Young Award in 1959.

88. Rocky Colavito, Indians, to Tigers for Harvey Kuenn, 1960. Kuenn had won the 1959 AL batting title. Colavito tied for the AL lead in homers. After Cleveland dealt its most popular player, subsequent lean years were attributed to “The Curse of Rocky Colavito.”

89. Robinson Cano, Edwin Diaz, Mariners, plus cash to Mets for Jay Bruce, Jarred Kelenic, Justin Dunn, Anthony Swarzak, Gerson Bautista, 2018. Brodie Van Wagenen swings for the fences in switch from agent to GM.

90. Bob Ojeda, Red Sox, with Tom McCarthy, John Mitchell, Chris Bayer to Mets for Calvin Schiraldi, Wes Gardner, John Christensen, La Schelle Tarver, 1985. Ojeda had a career year in 1986. Schiraldi gave up Ray Knight’s home run in Game 7.

91. Rogers Hornsby, Giants, to Braves for Jimmy Welsh and Shanty Hogan, 1928. Hornsby hit .361 in 1927 and filled in as Giants manager (32 games) for the ailing John McGraw. But owner Charles Stoneham became so annoyed with Hornsby that he sent him to Boston. “Rajah” responded by winning his seventh batting title.

92. Jose Bautista, Pirates, to Blue Jays for Robinson Diaz, 2008. Starting in 2010, Joey Bats made six straight All-Star Games.

93. Al Leiter, Marlins, with Ralph Milliard to Mets for AJ Burnett, Jesus Sanchez, Rob Stratton, 1998. Mets got in on Florida’s first post-World Series purge.

94. Willie McGee, Yankees, to Cardinals for Bob Sykes, 1981. McGee, a minor-leaguer, became a four-time All-Star and 1985 National League MVP.

95. Curt Schilling, Phillies, to Diamondbacks for Travis Lee, Omar Daal, Nelson Figueroa, Vicente Padilla, 2000. In 2001, the D-backs won the World Series.

96. Curt Schilling, Diamondbacks, to Red Sox for Casey Fossum, Brandon Lyon, Jorge De La Rosa, Mike Goss, 2003. In 2004, the Red Sox (finally) won the World Series.

97. Tris Speaker, Red Sox, to Indians for Sad Sam Jones, Fred Thomas and cash, 1916. No one was sadder than Boston fans when Speaker hit .386 in 1916.

98. Jack Boyle, Cincinnati Red Stockings, to St. Louis Browns for Hugh Nicol, 1886. Believed to be the first trade in baseball history.

99. David Wells, Tigers, to Reds for CJ Nitkowski, Mark Lewis, Dave Tuttle, 1995. Detroit had been talking with the Yankees about Wells and wanted a young reliever. But Mariano Rivera’s velocity suddenly spiked, so the Yankees pulled out (and signed Wells as a free agent the next year).

100. Sammy Sosa, Rangers, with Wilson Alvarez, Scott Fletcher to White Sox for Harold Baines, Fred Manrique, 1989. During the 2000 presidential campaign, former Rangers head George W. Bush was asked about his greatest regret and said, “Trading Sammy Sosa.” Who knew Baines would be a Hall of Famer in 2019?

101. Cliff Dapper, Dodgers, to Atlanta Crackers (Southern Association) for announcer Ernie Harwell, 1948. Legendary Brooklyn broadcaster Red Barber was out with a bleeding ulcer and the Dodgers wanted the best replacement available. The Crackers wanted compensation, so they took a catcher. Harwell reached the Hall of Fame.

Hall of Fame broadcaster Ernie Harwell on Oct. 3, 1993...

Hall of Fame broadcaster Ernie Harwell on Oct. 3, 1993 at Yankee Stadium during a Tigers broadcast. Credit: ASSOCIATED PRESS/Paul Hurschmann


FOR OUR BEST OFFER ONLY 25¢ for 5 months

Unlimited Digital Access.

cancel anytime.