Who has won the most MLB MVP titles and other coveted awards?

There is quite a list of awards a player can receive each year in the MLB.

The Most Valuable Player, created in 1930, is by far the oldest award. And little by little, the Baseball Writers’ Association of America has added more awards to the mix, from Manager of the Year to Golden Gloves.

While it’s not unusual for stars to win an award in the competition once in their career, it’s rare for someone to win 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 hunt for more.

The 2022 season saw Major League Baseball see 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 St. Louis Cardinals first baseman Paul Goldschmidt and New York Yankees outfielder Aaron Judge the reigning 2022 MLB MVPs, the question becomes: who will join baseball’s elite and over the course of win a handful of awards during their career? ?

Below you will find the crème de la crème, the people who have taken home the most important 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 still with the Pittsburgh Pirates, Bonds won his first National League MVP Award in 1990, hitting .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, made 46 appearances and finished the season with a .336 batting average. Nearly a decade later, in ’01, he had a monster MVP year. That year he hit .328/.515/.863, with 177 walks, 137 RBIs and a MLB record of 73 home runs. Bonds won the title the next three consecutive years, peaking 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 on four teams in both leagues. Clemens dominated baseball for three decades, winning titles 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, while 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 back-to-back Cy Young Awards and back-to-back pitching Triple Crowns, leading the league in ERA, wins and strikeouts. After a half-decade with the Yankees, where he picked up his sixth Cy Young, Clemens set the MLB record with the Astros in ’04. Nearly twenty years separated his first and last Cy Young win, the last of which came when he played on a National League team.

Awards for most Manager of the Year: 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 fell one game short of a spot in the World Series after finishing 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 collected his second Manager of the Year Award. In 2004, Cox won the award again, in addition to celebrating his 2,000th game as skipper. He continued to retain his place at the helm of the team in 2005, winning his final Manager of the Year Award after the Braves secured their 14th consecutive division title. The streak produced more titles than the franchise had previously won combined in Boston, Milwaukee and Atlanta.

2. Tony La Russa (1983, ’88, ’92, 2002)

La Russa earned his first Manager of the Year Award in 1983 with the Chicago White Sox, who improved dramatically 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 achieved a winning record in seven years. After the A’s finished first in the AL West in ’92, La Russa won his third trophy. His fourth Manager of the Year Award came in 2002 during his tenure as skipper of the St. Louis Cardinals, who defeated 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 had the best record because the season was shortened due to the strike). As skipper of the Texas Rangers, he won the award in 2004 after the team’s first finish above .500 in four years. He took home his third Manager of the Year Award in 2014, leading a once-terrible Baltimore Orioles team to their second playoff appearance since ’98. Showalter’s most recent award came in 2022, during 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 to ever take the mound – not just in pitching, but in fielding as well. Over the course of his 23-year career, the Hall of Famer became 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 another twelve years. After a brief hiatus in 2003, he won his last five from ’04 to ’08.

Most World Series MVP Awards: Tied for four players – two

1. Sandy Koufax (1963, ’65)

Koufax became the first player to win the World Series MVP twice, first taking it home during the Yankees’ sweep of the Los Angeles Dodgers 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 to top it off, he held Mickey Mantle to just one hit in seven at-bats, striking out three.

In the 1965 World Series, Koufax faced slightly tougher competition. He was defeated by Minnesota Twins ace Jim Kaat, taking the loss in Game 2 after allowing one earned run over six innings. He came back in Game 5 and pitched a shutout with 10 Ks and only one walk. And he got revenge on Kaat in Game 7, another 10-strikeout shutout to win 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 to the Yankees in Game 2, allowing four earned runs in eight innings. But like Koufax, he recovered impressively. Gibson pitched 10 innings in Game 5, striking out a whopping 13 batters and allowing no earned runs (but two runs scored). In Game 7, he gave up five runs, but still pitched a complete Game 7 and helped bring the Cards a championship.

Just three years later, he pitched nine innings of one-run ball and struck out ten 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 rest, he pitched another nine full innings in Game 7, striking out ten 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 two-run shot in the bottom of the third inning in Game 7. The A’s held on to their 5-2 lead, defeated the Mets and pulled out a win. title in succession.

Jackson played for the Yankees in ’77 and earned his nickname ‘Mr. October” in the autumn 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 with a two-out round tripper in the fifth. Jackson hit his third homer in the eighth and won his fourth World Series ring just an inning later.

4. Corey Seager (2020, ’23)

The star-studded Los Angeles Dodgers dominated throughout the shortened 2020 MLB season, but no player performed better in key moments than Corey Seager. He helped the Dodgers overcome a 3-1 deficit with five home runs in the NLCS against the Braves. In the World Series, Seager continued his success at the plate against the Tampa Bay Rays, finishing the series with an on-base percentage of .556.

Seager became the second player to win World Series MVP with different teams, leading the Texas Rangers to the title in 2023. He supplemented his offensive success with outstanding defensive play at shortstop, including a critical diving double play in the eighth inning of Game 3. The Rangers never looked back after this momentum-shifting moment, winning Games 3 and 4 before clinching the series against the Arizona Diamondbacks in five games.

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