There’s a hefty list of honors a player can receive in MLB each year.
The Most Valuable Player, originating in 1930, is by far the oldest award. And little by little, the Baseball Writers’ Association of America has added more accolades into the mix, from Manager of the Year to Gold Gloves.
While it’s not uncommon for stars to win a league accolade once in their career, it’s rare for one to nab these awards more than once. Mike Trout of the Los Angeles Angels is the only active player to have won three MLB MVP Awards. Bryce Harper of the Philadelphia Phillies is right behind him with two. And two-way player Shohei Ohtani is on the prowl for more.
In the 2022 season, Major League Baseball saw a pair of repeat winners. Ace Justin Verlander won his third Cy Young Award, and New York Mets’ skipper Buck Showalter won his fourth Manager of the Year Award.
With an array of talent like the St. Louis Cardinals first baseman Paul Goldschmidt and New York Yankees outfielder Aaron Judge, the 2022 reigning MLB MVPs, the question arises: Who will join baseball’s elites and win a handful of awards over the course of their career?
Listed below is the crème de la crème, those individuals who have taken home the most major awards in MLB history.
Most MVP Awards: Barry Bonds – Seven (1990, ‘92-93, 2001-04)
Bonds has by far the most MVP Awards in MLB history, surpassing the next 10 MVP winners who are tied with three each. While he was still with the Pittsburgh Pirates, Bonds won his first National League MVP Award in 1990, batting .301 with 33 home runs, 93 walks, and a career-high 52 steals. In ’92, the home run hitter won again, joining the 30-30 club for the second time with 34 round-trippers and 39 stolen bases.
In 1993 – the year he joined the San Francisco Giants – Bonds won his third NL MVP Award, going yard 46 times and ending the season with a .336 batting average. He had a monster MVP year almost a decade later in ’01. That year, he slashed .328/ .515/ .863, with 177 walks, 137 RBIs, and an MLB-record 73 home runs. Bonds won the title the next three consecutive years, topping out at .370 in ’02 and setting a majors record with 232 walks in ‘04.
Most Cy Young Awards: Roger Clemens – Seven (1986-87, ‘91, ‘97-98, 2001, ‘04)
Perhaps even more impressive than winning seven Cy Young Awards is winning them across four teams in both leagues. Clemens dominated three decades of baseball, taking home the title while playing for the Boston Red Sox, Toronto Blue Jays, Yankees and Houston Astros.
The Rocket won back-to-back Cy Young Awards in ’86 and ’87 with the Red Sox, leading the league in wins and ERA, and simultaneously winning AL MVP that first year. In 1991, he won again after finishing first in the majors with 241 strikeouts.
In his two seasons with the Blue Jays (1997-98), Clemens won consecutive Cy Young Awards and back-to-back pitching Triple Crowns, leading the league in ERA, wins and strikeouts. After half of a decade with the Yankees, where he nabbed his sixth Cy Young, Clemens set the MLB record in ’04 with the Astros. There was nearly a 20-year gap between his first and last Cy Young wins, the last of which while playing on a National League team.
Most Manager of the Year Awards: Three Managers Tied – Four
1. Bobby Cox (1985, ’91, 2004, ’05)
In ’85, Cox won his first Manager of the Year Award in the American League with the Blue Jays. They were one game short of a spot in the World Series after ending the season with a 99-62 record. Six years later, in his second year as manager of the Atlanta Braves, the team won the NL pennant, and he nabbed his second Manager of the Year Award. In 2004, Cox won the accolade once again, in addition to celebrating his 2,000th game as skipper. He continued to hold his place at the helm of the team in 2005, winning his last Manager of the Year Award after the Braves secured their 14th consecutive division title. The streak provided more titles than the franchise had won combined in Boston, Milwaukee and Atlanta before then.
2. Tony La Russa (1983, ’88, ’92, 2002)
La Russa secured his first Manager of the Year Award in 1983 with the Chicago White Sox, who drastically improved to a nearly 100-win season. As manager of the Oakland Athletics in ’88, he led the team to 104 wins. And prior to the previous season, they had not held a winning record in seven years. After the A’s placed first in the AL West In ’92, La Russa won his third award. His fourth Manager of the Year Award came in 2002 during his tenure as skipper of the St. Louis Cardinals, who swept the Arizona Diamondbacks in the NLDS.
3. Buck Showalter (1994, 2004, ’14, ’22)
After the ’94 season, Showalter won the Manager of the Year Award with the Yankees (who held the best record as the season was shortened due to the strike). As skipper of the Texas Rangers, he won the accolade in 2004 following the team’s first finish above .500 in four years. He took home his third Manager of the Year Award in 2014, bringing a once-terrible Baltimore Orioles team to their second playoff appearance since ’98. Showalter’s most recent award came in 2022 in his first year at the helm of the New York Mets. He led the team to 101 wins and their first postseason since 2016.
Most Gold Glove Awards: Greg Maddux – 18 (Pitcher)
Maddux is one of the best ever to take the mound – not only in terms of pitching but fielding too. Over the course of his 23-year career, the Hall of Famer won 18 Gold Gloves – more than any other position player in MLB history. He took home his first Gold Glove Award in 1990 and continued to do so for 12 more years. After a brief hiatus in 2003, he won his last five from ’04 to ’08.
Most World Series MVP Awards: Three Players Tied – Two
1. Sandy Koufax (1963, ’65)
Koufax became the first player to win World Series MVP twice, first taking it home in the Los Angeles Dodgers’ sweep of the Yankees in ’63. The Hall of Famer pitched complete games in Games 1 and 4 of the World Series. In the two games, he combined for 23 strikeouts and three earned runs. And as the cherry on top, he held Mickey Mantle to just one hit in seven at-bats, striking him out three times.
In the 1965 World Series, Koufax faced slightly tougher competition. Outdueled by Minnesota Twins ace Jim Kaat, he took the loss in Game 2 after allowing one earned run over six innings. He came back in Game 5, pitching a shutout with 10 Ks and just one walk. And he got his revenge on Kaat in Game 7, twirling yet another 10-strikeout shutout to earn his second title in three years.
2. Bob Gibson (1964, ‘67)
Both the ’64 and ’67 World Series went to seven games. In both decisive games, Gibson secured the title for the Cardinals. In 1964, the Hall of Famer was responsible for the loss against the Yankees in Game 2, giving up four earned runs in eight innings. But like Koufax, he recovered rather impressively. Gibson pitched 10 innings in Game 5, striking out a whopping 13 and allowing no earned runs (but two runs scored). In Game 7, he gave up five runs but still went on to pitch a complete Game 7 and help bring the Cards a championship.
Just three years later, he pitched nine innings of one-run ball and struck out 10 in Game 1 against the Red Sox. He returned for Game 5 and helped the Cards secure another win in a shutout. And with just two days of rest, he tossed another full nine-innings in Game 7, striking out 10 and winning his second ring.
3. Reggie Jackson (1973, ’77)
Unlike Koufax and Gibson, Jackson took home a pair of World Series MVPs as a member of two different teams. In the closely fought 1973 World Series, the All-Star outfielder knocked out a clutch two-run shot in the bottom of the third in Game 7. The A’s were able to hold onto their 5-2 lead, defeating the Mets and winning a back-to-back title.
Jackson played for the Yankees in ’77, earning his nickname “Mr. October” in the Fall Classic. In Game 6, he tied the MLB record for most home runs in a single game. He hit a two-run shot in the fourth inning and followed up with a two-out round tripper in the fifth. Jackson knocked his third homer out in the eighth and won his fourth World Series ring just an inning later.
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