Manny Ramirez‘s time with the Boston Red Sox was like a rollercoaster ride, full of incredible moments and unforgettable plays that defined his one-of-a-kind career. One of those standout moments occurred on May 14th, 2008. Ramirez did something that left fans and even his fellow players amazed. He caught a deep fly ball hit by Kevin Millar, but what happened next was pure Manny being Manny. He gave a high-five to a delighted Red Sox fan in the stands and then made an astonishing throw to Dustin Pedroia, who quickly relayed it to Kevin Youkilis for an unconventional and stylish double play.

But Manny’s time in Boston wasn’t just about the jaw-dropping plays. It was a mix of remarkable achievements and his signature quirks. Take, for instance, that time on July 18th, 2005, during a mound visit when Manny decided to take a spontaneous break inside the Green Monster. He disappeared for a moment, causing a bit of confusion, but he reappeared just in time as if nothing happened.

BOSTON – OCTOBER 5: Manny Ramirez #24 of the Boston Red Sox celebrates after connecting for a three-run home run to defeat the Los Angeles Angels, 6-3, in Game 2 of the American League Division Series at Fenway Park October 5, 2007 in Boston, Massachusetts. (Photo by Jim Rogash/Getty Images)

Manny’s milestones were etched in baseball history. On May 31st, 2008, he launched his 500th home run, marking an incredible achievement celebrated by fans at “Fenway South.” And who could forget his monstrous 491-foot home run on June 2nd, 2001, which still holds the record as the longest homer in the history of SkyDome (now Rogers Centre).

Amid the unforgettable feats, Manny’s personality shone through in moments like the 2007 ALDS walk-off home run that sent Red Sox fans into a frenzy of celebration. His presence was both electric and enigmatic, perfectly illustrated by his role in the memorable brawl during the 2003 ALCS with Roger Clemens.

Even the quirky and sometimes head-scratching moments, like cutting off a throw from Johnny Damon for no apparent reason, became part of Manny’s legend. Manny Ramirez’s time with the Red Sox wasn’t just a string of baseball games; it was a collection of stories that together created a complex and captivating portrait of a player who could deliver the extraordinary and the unexpected, often in the same breath.

• Manny Ramirez’s high-five double play

   

   

  On May 14th, 2008, Ramirez executed one of the most entertaining plays in recent memory: he caught a long fly ball hit by Kevin Millar, exchanged a high-five with a Red Sox fan in the stands, and then swiftly threw the ball to Dustin Pedroia, who relayed it to Kevin Youkilis, completing a stylish double play.

• Ramirez takes a break... in the Green Monster

   

  On July 18th, 2005, during a mound visit, Manny grew a bit restless and opted for a break. Coincidentally, the nearest ‘break room’ was nestled within the Green Monster as Manny briefly stepped out of the game. Fortunately, he returned just in time as the game resumed.

• Manny gets home run #500

   

  On May 31st, 2008, Ramirez launched a pitch from Chad Bradford into the stands of Camden Yards, marking his 500th home run. He received an ovation from the fans at ‘Fenway South’ and was mobbed by his teammates after the play.

• Manny’s 491-foot home run

   

   

  On June 2nd, 2001, against the Toronto Blue Jays, Ramirez obliterated a baseball, sending it soaring for a colossal 491-foot home run. This remarkable feat stands as the longest home run in SkyDome’s history (now known as Rogers Centre), a record that remains unbroken to this day.

• Ramirez’s first grand slam

   

  On August 19th, 2001, Manny provided Red Sox fans a glimpse of his legendary power by crushing a Calvin Maduro fastball into the Green Monster for his first career grand slam. The Red Sox went on to win the game 6-1.

• Manny walks it off

   

  During Game 2 of the 2007 ALDS, Ramirez stepped up to the plate with 2 outs in the bottom of the 9th inning. Seizing the opportunity to send the Red Sox faithful home with a smile, Ramirez delivered by walking the game off with a 3-run blast into the Green Monster, sparking pandemonium among fans.

• Back-to-back-to-back home runs

   

   

  Ramirez, along with David Ortiz and Kevin Youkilis, launched three consecutive home runs in Game 4 of the 2007 ALCS. While the Red Sox didn’t secure the victory, this moment etched itself as a classic in both Red Sox history and Manny’s career.

• Ramirez’s 3-run ALCS blast

   

   

  During game 5 of the 2003 ALDS, Ramirez smashed a three-run homer off of Cy Young winner Barry Zito, boosting the Red Sox ahead 4-1 in the sixth inning against the Oakland A’s. Manny’s clutch home run proved decisive, as the Red Sox secured a 4-3 victory and the team advanced to the ALCS.

• Manny and Pedro vs. Clemens and Zimmer

   

  While Game 3 of the 2003 ALCS is best remembered for Pedro Martinez tossing Don Zimmer to the ground, it was Ramirez who initially ignited the brawl. He charged the mound after Yankees pitcher and former Red Sox favorite Roger Clemens threw a pitch at his head. This action triggered the clearing of benches, resulting in chaotic scenes between these two long-standing rivals.

• Manny cuts off Damon

   

   

  While not exactly a positive play in Manny’s career, it deserves mentioning for its sheer absurdity. On July 21st, 2004 against the Baltimore Orioles, Ramirez would cut off a throw from Johnny Damon for no apparent reason, leading to a bizarre inside-the-park home run for David Newhan.

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