Tony Oliva: 55th Cooperstown Inductee connected to Puerto Rico’s Winter League

Tony Oliva

Tony Oliva is the 55th member of Cooperstown who played, managed, umpired, or did broadcasting work in Puerto Rico’s Winter League (PRWL), now the Roberto Clemente Professional Baseball League. Those players or umpires with @ also played in the Negro Leagues. This extensive list, with their PRWL team(s), Puerto Rico season(s), and year inducted in Cooperstown, includes:

  1. Rogers Hornsby (Ponce/Manager)-1942
  2. Roy Campanella (Caguas, Santurce and San Juan)-1969
  3. Leroy “Satchel” Paige (Guayama and Santurce)-1971
  4. Sandy Koufax (Caguas)-1972
  5. Joshua Gibson (Santurce)-1972
  6. Walter “Buck” Leonard (Mayagüez)-1972
  7. Montford “Monte” Irvin (San Juan)-1973
  8. Roberto Clemente (Santurce, Caguas and San Juan)-1973
  9. Oscar Charleston-1976[1]
  10. Willie Mays (Santurce)-1979
  11. Robert “Bob” Gibson (Santurce)-1981
  12. Hank Aaron (Caguas)-1982
  13. Frank Robinson (Ponce-Santurce/Manager)-1982
  14. Buck Canel-1985 (Ford C. Frick)[2]
  15. Ray Dandridge (Santurce)-1987
  16. Johnny Bench (San Juan)-1989
  17. Jim Palmer (Santurce)-1990
  18. Ferguson Jenkins (Caguas)-1991
  19. Reggie Jackson (Santurce)-1993
  20. Steve Carlton (Ponce)-1994
  21. Phil Rizzutto-1994[3]
  22. Leon Day (Aguadilla y Santurce)-1995
  23. Mike Schmidt (Caguas)-1995
  24. Earl Weaver (Santurce/Manager)-1996
  25. Jim Bunning (Caguas/Manager)-1996
  26. Tom Lasorda (Mayagüez, Santurce and Caguas)-1997
  27. Phil Niekro (Arecibo- Mayagüez)-1997
  28. Willie Wells (Aguadilla)-1997
  29. Larry Doby (San Juan)-1998
  30. Orlando Cepeda (Santurce)-1999
  31. Robin Yount (Santurce)-1999
  32. Nestor Chyalk-1999[4]
  33. Atanasio “Tony” Pérez (Santurce)-2000
  34. Sparky Anderson (San Juan/Manager)-2000
  35. Hilton Smith (Ponce)-2001
  36. Felo Ramírez-2001 (Ford C. Frick)[5]
  37. Eddie Murray (Caguas)-2002
  38. Gary Carter (Caguas)-2002
  39. Bob Uecker (Arecibo) 2003 (Ford C. Frick)[6]
  40. Wade Boggs (Bayamón) -2005
  41. Willard Brown (Humacao/Arecibo-Santurce)-2006
  42. Raymond Brown (San Juan-Santurce-Ponce)-2006
  43. Judd Wilson (Humacao)-2006
  44. Cal Ripken Jr. (Caguas)-2007
  45. Tony Gwynn (Bayamón-San Juan)-2007
  46. Rich Goosage (Ponce)-2008
  47. Ricky Henderson (Ponce)-2009
  48. Doug Harvey-2010[7]
  49. Roberto Alomar (Caguas-Ponce-San Juan-Santurce)-2011
  50. Iván Rodriguez-2017 (Caguas-Bayamón-Mayagüez)-2017
  51. Jack Morris (Mayagüez)-2018
  52. Jim Thome (Ponce) – 2018
  53. Lee Smith (Santurce)-2019
  54. Edgar Martínez (San Juan)-2019
  55. Tony Oliva (Arecibo)-2022

  1. [1] Umpire 1946-47
  2. [2] Radio commentator
  3. [3] Radio commentator
  4. [4] Umpire
  5. [5] Radio commentator
  6. [6] Played with Arecibo
  7. [7] Umpire

    # Bob Uecker was the only one of four (4) broadcasters who played in Puerto Rico.  Extensive research by Jorge Colón Delgado confirmed these Cooperstown inductees participated in pre-1938 barnstorming contests in Puerto Rico: Cristóbal Torriente, José de la Caridad Méndez, Louis Santop, Johnny Mize, Martín Dihigo, Alex Pompez (Cuban Stars executive), Effa Manley (Brooklyn Eagles executive) and umpire Bill Klem. Sources: Jorge Colón Delgado, Official Historian, Roberto Clemente Professional Baseball League, and Baseball Writers Association of America, 2022.

    Oliva’s connection to Jack McKeon

    Tony Oliva’s final season in the U.S. minors was in 1963, as RF for the 79-79 Dallas-Ft. Worth Rangers. AAA Pacific Coast League (PCL). Jack McKeon managed him. Fifty-nine years later, Oliva publicly thanked McKeon in his (Oliva’s) Cooperstown acceptance speech, July 24, 2022. “McKeon made me a better outfielder by hitting countless fly balls to me,” noted Oliva. “He deserves a lot of credit for my 1966 AL Gold Glove.” Oliva posted a .304/.347/.519 slash line with a .866 OPS for the Rangers, slamming twenty-three homers and driving in seventy-four.

    Oliva’s Batting Title: 1963-64 Arecibo Wolves

    Arecibo, in North Central Puerto Rico, had a Cuban skipper—Tony Castaño—and other Cuban players including Cookie Rojas and Miguel “Mike” Cuellar. Oliva, a native of Pinar del Río, Cuba, never played in the Cuban Winter League, but was comfortable in Puerto Rico and led the league with a .365 AVG, over Ponce’s Walter Bond (.349), San Juan’s Roberto Clemente (.345) and teammate Art López (.337). Santurce’s Orlando Cepeda had a .368 AVG, but not enough AB (133) to qualify for the batting crown in a 70-game season. “That was a special [winter] season, though we finished last (31-39),” recalled Art López. “Tony certainly benefitted from his season with Arecibo—showed the [Minnesota] Twins he was ready to hit big league pitching.”

    Oliva’s SABR bio by Peter Bjarkman incorrectly stated that Orlando Cepeda won the 1963-64 PRWL batting title, but indicated that Vic Power and Zoilo Versalles, with the 1963 Minnesota Twins, encouraged him (Oliva) to accept his “demotion” to AAA Dallas-Ft. Worth, after Minnesota initially planned to take Oliva north post-spring training. The author (later) conversed with Vic Power—a native of Arecibo—on a host of topics, including Oliva’s three AL batting titles and 1964 AL Rookie of the Year Award. “I made my AL debut with the 1954 Philadelphia A’s at age 26,” recalled Power, who affirmed he was ready for the majors earlier. “Tony (Oliva) was twenty-five going on twenty-six in that (1964) AL season with Minnesota. I encouraged him, in 1963, to be patient…”

    Licey Tigers Sign Oliva

    Vern Benson, Licey’s 1963-64 skipper, had played for the Havana Lions (aka Reds) in the 1952 Caribbean Series, and for Venezuela’s Pastora Milkers in the same event—two years later. He managed Santurce to the 1961-62 PRWL title and February 1962 Inter-American Series crown. Benson, who also coached at 3B for Licey, was pleased that Licey— “Blue Team”—signed Oliva at the end of the regular season and beyond, for the best-of-five semi-finals against Escogido (Red Team) and best-of-nine finals versus the Águilas Cibaeñas (AC), “Yellow Team,” (uniform colors). AC had a “convenio” (working agreement) with the Pittsburgh Pirates. Hence, Steve Blass and Willie Stargell played for AC.

    Coincidentally, Art López was recruited by 5 Estrellas, in Nicaragua, to reinforce them at the season’s end, and in their post-season. They emerged triumphant in the 1964 Inter-American Series over San Juan Senators, led by Roberto Clemente and Santurce reinforcement Orlando Cepeda. “I was aware that Tony was signed by Licey,” said López. “In my case, a colonel from Anastacio Somoza’s army came to Puerto Rico, toward [1963=64] season’s end, and flew me on a private jet, with a pilot and stewardess, to Miami, and then to Managua, Nicaragua.”

    Circling back to the Dominican Republic, Licey bested the “Red Team” (Escogido Lions) in the semi-finals, three games to two. Licey transformed itself with new players—Tony Oliva (RF), Phil Gagliano (SS), Miguel de la Hoz (3B) and Ray Barker (1B). Barker played for Arecibo Wolves; de la Hoz was Santurce’s 3B. John Boozer (Arecibo) and Fred Talbot (Caguas) reinforced Licey. Santurce’s Rubén Gómez reinforced Escogido, managed by his close friend, Pepe Lucas. Rubén took Juan Marichal’s roster spot. (SF did not allow Marichal, 7-4, 1.36 ERA, in the regular season, to pitch in the post-season.) Rubén (1-2, 4.15 ERA), future Cooperstown Hall of Famer Gaylord Perry (1-1, 2.53 ERA), plus Danilo Rivas and Phil Ortega pitched for Escogido. “I alerted [then, Santurce owner] Pedrín Zorrilla, back in 1950, to sign Pepe Lucas, after seeing him play in a Dominican Republic series,” recalled Rubén. “He was short of Escogido pitchers for the 1963-64 playoffs, so I said yes.”

    AC were favored for the finals, adding Arecibo 2B Octavio “Cookie” Rojas and Ponce OF Walter Bond. Licey added catcher Jackie Moore, OF Félix Juan Maldonado (from Santurce), and RHP Alan Koch, with Mayagüez. AC took the first three at home, January 25-27, 1964, behind the pitching of Blass, Troy Giles, and Ben Johnson. Games Four-Seven took place in Santo Domingo. Oliva ran through a Benson stop sign, from the 3B coaching box, to score the winning run, January 28, 1964—a 7-6 Licey walk-off win. Stargell’s throw from LF was “off the mark.” Licey then recorded three straight wins at home, before closing out the series in Santiago, on February 1. “Tony was determined to score the winning run,” recalled Benson. “He got an A+ for his enthusiasm.”

    Oliva went 3-for-8 for Licey in the regular season, followed by 8-for-21 (.381 AVG) versus Escogido and 10-for-29, a .345/.424/.586 slash line, and 1.010 OPS against AC in the finals. He later (1967-68 and 1968-69) played for AC toward the season’s end and in their semi-final series.

    Jim Kaat’s 1958 link to Jack McKeon

    Jim Kaat had one year of college—at Hope College, Holland, Michigan—when he signed a $4,000 bonus with the Washington Senators in 1957 and was assigned to Class D Superior Senators, Nebraska State League. They finished 27-29, tied for sixth in the eight-team loop. Kaat went 5-6 with ninety-five strikeouts and thirty-five walks in seventy-three innings and was promoted to Class C Missoula Timberjacks, seven-team Pioneer League, whose player/MGR was Jack McKeon, a 27-year-old catcher. McKeon (.263/.358/.376 slash line and .733 OPS) helped turn Kaat’s pitching career around after a 1-4 start with Missoula. Kaat, in his July 24, 2022, Cooperstown acceptance speed, noted he was one more start from being released when McKeon told him: “Kid, you’re going to pitch in the big leagues.” Kaat went 15-5 the rest of the way for 70-59 Missoula to finish 16-9 with a league-leading 2.99 ERA and 245 strikeouts in 223 innings!

    Kaat: 1959-60 Nicaragua Winter League

    A 20-year Kaat was 8-8, 4.10 ERA for the 1959 Chattanooga Lookouts, Class AA Southern Association. He then pitched for the Boer Indians, in Nicaragua’s Winter League, a four-team loop. Dick Stigman, another lefty at the AAA level (San Diego Padres), was part of Boer’s rotation, managed by Earl Torgeson, a member of the 1959 Chicago White Sox, AL champions. A key game occurred on December 15, 1959, when the León Lions bested Boer to win the season’s first half by one game, at 19-11, over Boer’s 18-12 mark. Legendary Boston Red Sox player Johnny Pesky managed 5 Estrellas. Roster changes were common. Boer signed Twins prospect Don Mincher to be their clean-up hitter. Pesky arranged for 5 Estrellas to sign Walter Bond, a Cleveland Indians farmhand. León defeated 5 Estrellas in the finals. Ferguson Jenkins, with 1962-64 León, pitched in Nicaragua after Kaat’s 1959-60 season with Boer. They are that league’s only Cooperstown player inductees. Broadcaster Felo Ramírez did radio transmissions in Nicaragua, in the mid-1960s.

    Cooperstown Hall of Famers in Winter and Summer Leagues, excluding Puerto Rico

    Brooks Robinson, 1955-56 Willard Blues, Colombia’s Winter League, and Willie McCovey, with 1956-57 Vanytor, are Cooperstown’s two members who played there. Robinson also played for 1957-58 Cienfuegos Elephants, in Cuba. Transitioning to the Dominican Republic, here are their Cooperstown inductees:

    • Martín Dihigo, 1929 Escogido Lions, 1937 AC player/MGR, 1951 AC skipper and 1952 Escogido MGR
    • Josh Gibson, 1937 Ciudad Trujillo Dragons
    • Satchel Paige, 1937 Ciudad Trujillo
    • Cool Papa Bell, 1937 Ciudad Trujillo
    • Willard Brown, 1951 and 1952 Escogido
    • Ray Dandridge, 1954 Escogido
    • Bill Mazeroski, 1955-57 AC
    • Earl Weaver, 1955-56 AC
    • Sparky Anderson, 1956-57 Escogido
    • Juan Marichal, 1957-60, 1963-65, 1967-68, 1973-74 Escogido
    • Willie McCovey, 1957-59 Escogido
    • Bob Gibson, 1958-59 Licey
    • Willie Stargell, 1963-64 AC
    • Gaylord Perry, 1963-64 Escogido
    • Minnie Miñoso, 1963-64 Escogido
    • Tony Oliva, 1963-64 Licey; 1967-69 AC
    • Ferguson Jenkins, 1964-65 Escogido (finals)
    • Phil Niekro, 1966-67 Estrellas Orientales (EO)
    • Rollie Fingers, 1970-71 EO
    • Tommy Lasorda, 1970-71 Escogido MGR; 1972-76 Licey MGR
    • Tony LaRussa, 1970-71 AC and Escogido, 1972-73 Escogido
    • Jim Bunning, 1976-77 Escogido MGR
    • Pedro Martínez, 1988-91, 1996-2000, 2002, Licey; 1991-93, Azucareros del Este; 1994-96, Escogido
    • Vladimir Guerrero, 1995-97, 2001-02, EO; 2004-05 and 2012-13, Licey
    • David Ortiz, 1994-2004 and 2005-06 Escogido

    Cuba’s Winter League list of Cooperstown inductees comprises:

    • José de la Caridad Méndez
    • Cristóbal Torriente
    • Martín Dihigo
    • Oscar Charleston
    • Raymond Brown
    • Willard Brown
    • Cool Papa Bell
    • Josh Gibson
    • Satchel Paige
    • Jim Bunning
    • Ray Dandridge
    • Leon Day
    • Rube Foster
    • Pete Hill
    • Monte Irvin
    • Judy Johnson
    • Tommy Lasorda
    • Alex Pompez
    • Brooks Robinson
    • Louis Santop
    • Hilton Smith
    • Turkey Stearnes
    • Willie Wells
    • Hoyt Wilhelm
    • Joe Williams
    • Jud Wilson
    • Early Wynn
    • Buck Canel (Ford C. Frick Award in 1985)
    • Felo Ramírez (Ford C. Frick Award in 2001)
    • Minnie Miñoso

    Mexico’s Pacific (Winter) League Cooperstown Connection

    One of the author’s favorite players—Rickey Henderson—played for the 1978-79 Mayos de Navojoa in Mexico’s Pacific League, the winter loop. Henderson represented Mexico in the February 1979 Caribbean Series hosted by San Juan, Puerto Rico, and was named LF on the Series All-Star Team. (Henderson’s 44 SB for the 1980-81 Ponce Lions, PRWL, is the single-season standard for that league; He accomplished this in just forty-eight games.) Here is the list:

    • Raymond Brown, Obregón, 1948-49
    • Ray Dandridge, Obregón, 1948-49#
    • Buck Leonard, Obregón, 1951-52
    • Willie Wells, Obregón, 1955-56#
    • Bob Lemon, Hermosillo, 1945-46
    • Whitey Ford, Mazatlán, 1948-49
    • Whitey Herzog, Navojoa, 1954-55
    • Dave Winfield, Obregón, 1973-74
    • Frank Robinson, Culiacán player/MGR, 1977-78
    • Rickey Henderson, Navojoa, 1978-79 (22 SB in forty-four games)
    • Larry Walker, Hermosillo, 1987-88
    • Mike Piazza, Mexicali, 1991-92

    #Dandridge and Wells played many summers in Mexico. A partial list of Cooperstown inductees who played in the summer Mexican League includes Cool Papa Bell, Josh Gibson, Satchel Paige, Martín Dihigo, Roy Campanella, Monte Irvin, to name a few.

    Venezuelan Winter League

    Roy Campanella played two winter seasons in Venezuela, at the onset of that league. He made his league debut following a November-December 1945 barnstorming trip in Venezuela by the American All-Stars, comprised of Negro Leaguers, including Jackie Robinson and Buck Leonard. Miguel Dupouy Gómez wrote a fine blog on this barnstorming trip. Venezuelan League (including the Occidental League) Cooperstown inductees include:

    • Roy Campanella, Sabios de Vargas, 1946 and 1947-48 (career .342 AVG and .567 SLG)
    • Hilton Smith, Sabios de Vargas, 1946-47 (8-5, 2.38 ERA and .369 AVG)
    • Raymond Brown, Sabios de Vargas, 1949-50
    • Martín Dihigo, Caracas Lions MGR, 1952-53#
    • Luis Aparicio, many teams, from Gavilanes (1953-54) and concluding, age 40, 1974-75 Lara Cardinals
    • Bob Gibson, Oriente, and Valencia, 1960-61 (1.12 ERA in the Venezuela post-season)
    • Felo Ramírez, 1961-62 Caracas Lions broadcaster (Ford C. Frick Award in 2001)
    • Earl Weaver, Lara MGR, 1962-63
    • Sparky Anderson, Magallanes MGR, 1964-65
    • Rod Carew, Aragua player-MGR, 1971-72, Aragua, 1972-73##
    • Bobby Cox, Lara MGR, 1974-77
    • Buck Canel, broadcaster, Lara, 1976-77 (Ford C. Frick Award in 1985)
    • Mariano Rivera, Aragua, 1991-92##

    #Dihigo, Josh Gibson, and Johnny Mize played for the Concordia Eagles, a famous Venezuelan barnstorming team, early-to-mid 1930s. Gibson joined the 1940 Centauros de Maracaibo. Leon Day did likewise for 1940 Vargas. ##Carew and Rivera are natives of Panamá but never played winter ball there.


    Jack McKeon, the only manager in minor league and MLB to win over 1,000 games at both levels, was 1,051-990-1 (.515 PCT), in sixteen big league seasons, capped by an 11-7 playoff run with the 2003 Florida Marlins, winners of the Fall Classic in six games versus the New York Yankees. McKeon, at age 72, was the oldest MLB MGR to win a Fall Classic. In seventeen minor-league campaigns, 1955-1964, 1968-1972, 1976 and 1979, his clubs were 1,220-1,221 (.500 PCT). He experienced success with Arecibo and Santurce in the 1970s, leading Arecibo to a 36-24 (.600 PCT) finish in 1977-78. He managed RHP Paul Hartzell, with 1976-77 Santurce. Hatzell spoke highly of McKeon’s temperament and managing ability. McKeon was George Brett’s first MGR with the 1973 Kansas City Royals. (Brett went 13-for-22 off Hartzell, a .591 AVG, in AL play.) McKeon initially managed Arecibo in 1970-71, replacing Tony Castaño.

    There were a number of reasons why McKeon endeared himself to the PRWL. For one, he continued managing in the league after his initial big league managing stint with the 1973 Kansas City Royals. McKeon believed in being competitive and giving young Native players a chance to prove themselves. His outgoing personality captivated the fans. “I had a lot of good rapport with the fans and Puerto Rican players,” said McKeon. “They remember me as a manager who always gave the kids—Candy Maldonado, Carlos Lezcano, Mario Ramírez—a chance to play. I was trying to get these kids enough playing time so we could build up experience and not have to worry about imported players. It was time to begin infiltrating them and build some tradition and depth of Arecibo’s Native players.”

    Thanks to Vern Benson, Rubén Gómez, Paul Hartzell, Rickey Henderson, Art López, Jack McKeon and Vic Power for their insights. Tito Rondón’s 2013 blog on the 1959-60 Nicaraguan Winter League season was helpful. Ditto for Miguel Dupouy Gómez’s 2019 blog, November-December 1945 American All-Stars Series in Venezuela. Jorge Colón Delgado furnished photos and editorial assistance.

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