20 MLB Stars Who Lived Like It Was Always the Offseason

For most players, the MLB offseason is a time to rest, recover, and maybe enjoy beach time. But for some stars, the offseason mindset wasn’t just a break in the schedule—it was a lifestyle.

Whether they were globe-trotting or just enjoying the finer things a little too often, these guys seemed to treat baseball as a side hustle. Here are 20 MLB stars who lived like it was always the offseason, no matter what month it was.

20. 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 brought wild energy to the field and even more chaos off of it. He never seemed too far from offseason mode, from flashy cars to unpredictable antics.

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 saying—it was a full-blown lifestyle. The man played like a legend and partied like he didn’t have a game the next day.

18. Jose Canseco

May 23, 2013; Fort Worth, TX, USA; Fort Worth Cats designated hitter Jose Canseco (33) reacts to striking out in the bottom of the first inning of the game against the Edinburg Roadrunners at LaGrave Field in Fort Worth. Mandatory Credit: Tim Heitman-Imagn Images
Tim Heitman-Imagn Images

Canseco lived large on and off the diamond, often making headlines for things that had nothing to do with baseball. Whether it was reality TV or wild business ideas, he was always up to something.

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

Harper’s fashion choices, hair routine, and love for the spotlight scream offseason vibes year-round. He somehow makes a walk to first base feel like a runway strut.

16. A.J. Burnett

Oct 3, 2015; Pittsburgh, PA, USA; Pittsburgh Pirates starting pitcher A.J. Burnett (34) pitches against the Cincinnati Reds during the fifth inning at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images
Charles LeClaire-Imagn Images

With his full-sleeve tattoos and devil-may-care attitude, Burnett seemed more like a rock band roadie than a pitcher. His vibe was all rebellion, all the time.

15. 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

Damon’s post-Red Sox life was a constant highlight reel of yachts, cocktails, and TV appearances. He looked like he belonged more at a pool party than batting practice.

14. Derek Holland

Sep 19, 2021; St. Petersburg, Florida, USA; Detroit Tigers relief pitcher Derek Holland (49) throws a pitch during the eighth inning against the Tampa Bay Rays at Tropicana Field. Mandatory Credit: Mike Watters-Imagn Images
Mike Watters-Imagn Images

Nicknamed “The Dutch Oven,” Holland spent as much energy doing impressions and jokes as he did throwing pitches. The man practically auditioned for SNL mid-season.

13. David Wells

Apr 24, 2007; Phoenix, AZ, USA; San Diego Padres pitcher (33) David Wells against the Arizona Diamondbacks at Chase Field in Phoenix, AZ. Mandatory Credit: Mark J. Rebilas-Imagn Images Copyright © 2007 Mark J. Rebilas
Mark J. Rebilas-Imagn Images

Wells famously threw a perfect game while possibly hungover, which tells you all you need to know. If anyone blurred the line between game day and party day, it was Boomer.

12. Josh Hamilton

Texas Rangers Josh Hamilton had the crowd going during the first round of the MLB Home Run Derby at Yankee Stadium in the Bronx July 14, 2008. Although Hamilton didn't win the derby, he did hit a record-setting 28 first-round dingers, including 13 straight on 13 swings.
Frank Becerra Jr / USA TODAY NETWORK

Hamilton had real demons, but even during his comeback, he carried the aura of someone who could ditch a series for a tropical escape. His story is a rollercoaster of talent and turmoil.

11. Jason Giambi

Sep 14, 2014; Detroit, MI, USA; Cleveland Indians pinch hitter Jason Giambi (72) pops up to end the game against the Detroit Tigers at Comerica Park. Detroit won 6-4. Mandatory Credit: Rick Osentoski-Imagn Images
Rick Osentoski-Imagn Images

Giambi’s bleach-blond hair and love of Vegas gave him full offseason energy even in the thick of July. He looked like he’d rather be in a cabana than a clubhouse.

10. Noah Syndergaard

Aug 27, 2023; Toronto, Ontario, CAN; Cleveland Guardians starting pitcher Noah Syndergaard (34) delivers a pitch against the Toronto Blue Jays in the fourth inning at Rogers Centre. Mandatory Credit: Dan Hamilton-Imagn Images
Dan Hamilton-Imagn Images

Thor’s off-field presence was a whole brand—movie cameos, fashion shoots, and living like a Norse god. Baseball felt like just another epic quest in his myth.

9. 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 was always doing Rickey things, and that included showing up with offseason swagger no matter the game situation. From third-person quotes to unexpected off-field stunts, he lived in his world.

8. Barry Zito

San Francisco Giants pitcher Barry Zito pitches against the Milwaukee Brewers during the spring game at Scottsdale Stadium March 4, 2010. Sr Giants0306 163374
David Wallace / The Arizona Republic, Arizona Republic via Imagn Content Services, LLC

Zito played guitar, surfed, and had a vibe that screamed “California offseason.” Even when pitching, it felt like he was waiting for a meditation retreat.

7. Joba Chamberlain

Jun 13, 2016; Kansas City, MO, USA; Cleveland Indians pitcher Joba Chamberlain (62) delivers a pitch against the Kansas City Royals during the eighth inning at Kauffman Stadium. Mandatory Credit: Peter G. Aiken-Imagn Images
Peter G. Aiken-Imagn Images

Joba had the talent, the hype, and the look of someone who enjoyed the nightlife just as much as a seventh-inning jam. He brought bullpen arm energy and VIP booth swagger.

6. Jose Reyes

Mets manager Willie Randolph celebrates with Jose Reyes after the Mets defeated the Yankees 10 - 3 in the second game of the subway series at Yankee Stadium June 26, 2005
Frank Becerra Jr./The Journal News / USA TODAY NETWORK

Reyes was always dancing, smiling, and living on vacation. His mood never changed, whether it was the All-Star break or Game 7.

5. Mark Fidrych

Mark Fidrych
ERIC SEALS / Imagn Content Services

“The Bird” was pure chaos, talking to the baseball and grooming the mound like it owed him money. His energy was offseason-level weird, all year long.

4. 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 lived big, dated celebrities, and gave off offseason millionaire vibes before, during, and after games. If there was a camera around, he knew how to find it.

3. Mike Napoli

Mar 4, 2018; Phoenix, AZ, USA; Cleveland Indians first baseman Mike Napoli (32) bats against the Milwaukee Brewers during the first inning at Maryvale Baseball Park. Mandatory Credit: Joe Camporeale-USA TODAY Sports
Joe Camporeale-Imagn Images

Napoli’s shirtless parade celebration became a whole personality. He leaned hard into the offseason lifestyle, even when October was still in full swing.

2. Nyjer Morgan

Nyjer Morgan celebrates his double in the 4th inning with the beast move. The Milwaukee Brewers and the Arizona Diamondbacks play game 5 of the NLDS at Miller Park Friday October 7, 2011. Brewers08 Spt Lynn 15
Tom Lynn, Milwaukee Journal Sentinel

Morgan’s alter ego, “Tony Plush,” acted like baseball was just one of many roles in his entertainment career. Interviews, celebrations, and tweets—he made every day feel like spring break.

Read More: Home Run Kings: Ranking the 30 Best in MLB History

1. 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 lived the offseason dream 24/7. From gold chains to mic-drop moments, Ortiz carried himself like a man who never fully clocked back into work, and we loved every second of it.

Read More: Jose Ramirez had a Quick Nap After Being Hit By Pitch at the Plate

Related Articles
Jun 19, 2025; San Francisco, California, USA; Indiana Fever guard Caitlin Clark (22) reacts during the fourth quarter against the Golden State Valkyries at Chase Center. Mandatory Credit: Darren Yamashita-Imagn Images
ESPN Slammed for Mistakes During Fever-Aces Broadcast
Fans Rip ESPN Over Fever-Aces Broadcast Blunders ESPN is under fire after a string of mishaps during...
Read More
Jun 22, 2025; Washington, District of Columbia, USA; Dallas Wings guard Paige Bueckers (5) dribbles the ball as Washington Mystics guard Sonia Citron (22) defends in the first half at Entertainment & Sports Arena. Mandatory Credit: Geoff Burke-Imagn Images
WNBA: Top 5 Storylines Shaping the 2025 Season
1. The Liberty Might Be Even Better Than Last Year Fresh off a 2024 WNBA championship, the New York Liberty...
Read More
Oct 8, 2015; St. Louis, MO, USA; Edmonton Oilers center Connor McDavid (97) skates on the ice against the St. Louis Blues during the first period at Scottrade Center. Mandatory Credit: Jasen Vinlove-USA TODAY Sports
Ranking the Top 7 Best NHL Drafts of All Time
These NHL Draft Classes Changed the League Forever The NHL Draft isn’t just a yearly tradition,...
Read More

As an Amazon Associate, The Quick Report earns from qualifying purchases.

Part of the Castaway Studios media network.