19 MLB Stars Who Cashed In Just For Being Cool

Baseball might be all about stats and championships on paper, but in the real world? Coolness pays. And some guys just had the swagger, the style, and the presence to turn their vibes into serious checks.

Whether it was a killer smile, a signature bat flip, or just the way they wore their uniform, these MLB stars knew how to stand out. They weren’t always the best on the field, but they sure were magnetic off it.

19. Manny Ramirez

July 18, 2008; Anaheim CA, USA; Boston Red Sox left fielder Manny Ramirez (24) hits a single in the second inning against the Los Angeles Angels at Angel Stadium of Anaheim. Mandatory Credit: Gary A. Vasquez-Imagn Images
Gary A. Vasquez-Imagn Images

Manny being Manny wasn’t just a catchphrase—it was a business model. Even when he wasn’t paying attention in the outfield, brands and fans couldn’t get enough.

18. Ken Griffey Jr.

Ken Griffey Jr. won the 1998 Home Run Derby at Coors Field.
Robert Deutsch / USA TODAY NETWORK

Griffey’s backwards hat alone probably deserves a shoe deal. He made baseball look smooth and effortless, and every kid wanted to be him.

17. Bryce Harper

May 24, 2025; West Sacramento, California, USA; Philadelphia Phillies first baseman Bryce Harper (3) hits an RBI single against the Athletics during the first inning at Sutter Health Park. Mandatory Credit: Dennis Lee-Imagn Images
Dennis Lee-Imagn Images

From his wild hair to his eye black game, Harper has always had a flair for the dramatic. Even when the bat goes cold, the endorsements stay hot.

16. Derek Jeter

Sep 25, 2014; New York, NY, USA; New York Yankees shortstop Derek Jeter (2) warms up prior to the game against the Baltimore Orioles at Yankee Stadium. Mandatory Credit: William Perlman/NJ Advance Media for NJ.com via Imagn Images
NJ Advance Media for NJ.com-Imagn Images

Jeter had the clean image, the New York spotlight, and a dating history that read like a red carpet lineup. He was the blueprint for “cool and collected” cashing in.

15. Shohei Ohtani

May 30, 2025; Los Angeles, California, USA; Los Angeles Dodgers designated hitter Shohei Ohtani (17) pops out during the eighth inning against the New York Yankees at Dodger Stadium. Mandatory Credit: Jason Parkhurst-Imagn Images
Jason Parkhurst-Imagn Images

Ohtani’s on-field talent is unmatched, but let’s be honest—the smile, the humility, the global charm? That’s the money-maker.

14. Tim Anderson

May 25, 2025; Anaheim, California, USA; Los Angeles Angels shortstop Tim Anderson (77) forced out at first base against the Miami Marlins during the sixth inning at Angel Stadium. Mandatory Credit: Jonathan Hui-Imagn Images
Jonathan Hui-Imagn Images

He bat-flipped his way into baseball’s cool club. With swagger to spare, he became the face of the game without needing a Hall of Fame resume.

13. Johnny Damon

10/26/2004 -- St. Louis, MO -- World Series Game 3 - Boston Red Sox vs. St. Louis Cardinals -- Johnny Damon hits a foul in the fifth inning. Robert Deutsch, USA TODAY staff (Via MerlinFTP Drop) Xxx World Series Dec 386 Jpg S Bbo Usa Mo
Robert Deutsch, USAT via Imagn Content Services, LLC

That flowing hair and laid-back vibe made him marketable in both Boston and New York—no easy feat. He cashed in on being baseball’s version of a rock star.

12. José Bautista

Mar 3, 2024; Las Vegas, Nevada, USA; Former baseball player and Las Vegas Lights FC owner Jose Bautista attends the Pennzoil 400 at Las Vegas Motor Speedway. Mandatory Credit: Gary A. Vasquez-Imagn Images
Gary A. Vasquez-Imagn Images

One iconic bat flip turned him into a legend overnight. He rode that moment into marketing gold and forever stayed in the cool kid club.

11. Yasiel Puig

Cincinnati Reds shortstop Jose Iglesias (4) runs for first as he hits a solo home run to center field in the seventh inning of the MLB National League game between the Cincinnati Reds and the Chicago Cubs at Great American Ball Park in downtown Cincinnati on Wednesday, May 15, 2019. The Reds won 6-5 on a walk-off single by Yasiel Puig in the bottom of the 10th inning. Chicago Cubs At Cincinnati Reds
Sam Greene, Cincinnati Enquirer via Imagn Content Services, LLC

Puig’s energy was chaotic, but undeniably entertaining. His unpredictable style made him a must-watch TV—and brands took notice.

10. Alex Rodriguez

Aug 24, 2024; Bronx, New York, USA; Former New York Yankees third baseman Alex Rodriguez at Yankee Stadium. Mandatory Credit: Wendell Cruz-Imagn Images
Wendell Cruz-Imagn Images

A-Rod went from polarizing to polished in real quick time. These days, he’s cooler as a businessman than he ever was as a shortstop.

9. Mookie Betts

May 24, 2025; New York City, New York, USA; Los Angeles Dodgers shortstop Mookie Betts (50) hits a single in the sixth inning against the New York Mets at Citi Field. Mandatory Credit: Wendell Cruz-Imagn Images
Wendell Cruz-Imagn Images

Mookie has the rare combo of elite play and absolute chill. He makes bowling cool and rocks a gold chain like it’s part of the uniform.

8. Fernando Tatís Jr.

May 27, 2025; San Diego, California, USA; San Diego Padres outfielder Fernando Tatis Jr. (23) rounds the bases after hitting a solo home run during the first inning against the Miami Marlins at Petco Park. Mandatory Credit: Denis Poroy-Imagn Images
Denis Poroy-Imagn Images

Tatís has flash, flair, and a social media-friendly smile. Even when he’s suspended, he somehow stays in the spotlight.

7. Joe Mauer

Aug 3, 2024; Minneapolis, Minnesota, USA; Minnesota Twins former player Joe Mauer throws a ceremonial pitch as the team honors his recent induction into the Baseball Hall of Fame before a game against the Chicago White Sox at Target Field. Mandatory Credit: Bruce Kluckhohn-Imagn Images
Bruce Kluckhohn-Imagn Images

He wasn’t flashy, but the “Minnesota Nice” thing worked like a charm. Clean-cut, calm, and clutch—he was the face of every Midwestern brand’s dream.

6. Josh Donaldson

Apr 13, 2017; Toronto, Ontario, CAN; Toronto Blue Jays designated hitter Josh Donaldson (20) loses his bat on a ground ball hit to Baltimore Orioles third baseman Manny Machado (not pictured) during the fourth inning at Rogers Centre. Mandatory Credit: John E. Sokolowski-Imagn Images
John E. Sokolowski-Imagn Images

With his mohawk and fiery persona, Donaldson gave off big “don’t mess with me” energy. That edge made him a magnet for attention and sponsorships.

5. David Ortiz

Oct 10, 2016; Boston, MA, USA; Boston Red Sox designated hitter David Ortiz (34) tosses the pine tar rag before hitting in the fourth inning against the Cleveland Indians during game three of the 2016 ALDS playoff baseball series at Fenway Park. Mandatory Credit: Bob DeChiara-Imagn Images
Bob DeChiara-Imagn Images

Big Papi could charm anyone from little leaguers to late-night hosts. His larger-than-life personality translated into post-career success just as easily.

4. Javier Báez

Jun 4, 2025; Chicago, Illinois, USA; Detroit Tigers center fielder Javier Baez (28) hits an RBI-single against the Chicago White Sox during the first inning at Rate Field. Mandatory Credit: Kamil Krzaczynski-Imagn Images
Kamil Krzaczynski-Imagn Images

Even when the bat’s not cooperating, Javy still looks cool. The glove work, the tags, the style—it all adds up to marketability.

3. Bo Jackson

July 11, 2010; Anaheim, CA, USA; Kansas City Royals former player Bo Jackson bats during the 2010 All Star celebrity softball game at Angel Stadium. Mandatory Credit: Kirby Lee/Image of Sport-Imagn Images
Kirby Lee-Imagn Images

Bo didn’t even need to play baseball full-time to make a profit. Just being Bo was enough to sell shoes, video games, and just about anything else.

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2. Reggie Jackson

July 1980; Cleveland, OH,USA; FILE PHOTO; New York Yankees right fielder Reggie Jackson in action against the Cleveland Indians at Cleveland Stadium during the 1980 season. Mandatory Credit: Malcolm Emmons-Imagn Images
Malcolm Emmons-Imagn Images

Mr. October didn’t just hit homers—he hit marketing gold. Sunglasses, quotes, and ego all combined into one very cool and very profitable package.

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1. Rickey Henderson

Jun 1, 1995; Oakland, CA, USA; Rickey Henderson of the Oakland Athletics in action against the New York Yankees at the Oakland Coliseum. Mandatory Credit: Photo By Imagn Images Copyright (c) 1995 Imagn Images
Imagn Images

Rickey spoke in third person and slid like nobody else. His vibe was unmatched, and his coolness made him a brand long before the concept of personal branding existed.

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