David Ortiz Begging Tom Brady to Stay a Patriot Was One Time Big Papi Couldn’t Win

Tom Brady and David Ortiz always seemed to share the spotlight.

For the past two decades, the two men have won multiple championships and countless hearts, giving the fans of the Boston Red Sox and New England Patriots — franchises that had gone a combined 127 years without a championship before Brady and Ortiz came along — more thrills and Duck Boat parades than anyone in New England could have ever hoped for.

This week, these two men were back at the forefront of their sports, although for very different reasons. On Sunday, Brady’s Tampa Bay Buccaneers lost in heartbreaking fashion in the Divisional Round of the NFL Playoffs, and Brady, at age 44, gave mixed messages but seemed to be considering retirement more seriously than at any other time in his career.

Ortiz had been retired since 2016, which meant his five-year waiting period to appear on the Baseball Hall of Fame ballot was over, and on Tuesday, he would learn if he was to be the first designated hitter ever elected in his first year on the ballot.

Brady’s answer was, essentially, a maybe. Ortiz’s answer was a definitive yes. Big Papi is in the Hall of Fame. Brady will be soon. Two of the greatest winners in Boston sports history, forever friends, forever linked.

The cross-sports friendships among Boston’s best go back a long way

Boston is a big sports city, but it really functions as a small town. Like the song says, everyone knows your name, and the four major sports teams are always well aware of how the others are doing.

In the 2000s, Red Sox manager Terry Francona and Celtics head coach Doc Rivers developed a deep friendship, and Francona at times seemed more interested in how the Celtics were faring during the 2008 NBA Finals than his own team, constantly asking reporters after Red Sox games for score updates across town at TD Garden.

Of course, Ortiz and Celtics star Kevin Garnett were longtime friends from their days playing on teams in Minnesota. And you could always count on Brady and other Patriots, as well as champion Celtics and Bruins, to throw out first pitches all four years the Red Sox held World Series ring ceremonies on Opening Day at Fenway Park.

Brady was there for Big Papi in his time of terrible crisis

Occasionally, Brady and Ortiz had big days at their places of work on the same day. On Oct. 13, 2013, Brady’s Patriots took on the New Orleans Saints at Foxboro Stadium in the afternoon, before the Red Sox hosted the Detroit Tigers in Game 2 of the American League Championship Series.

In the matinee, Brady completed a frantic comeback in the final minute, hitting Kenbrell Thompkins for the winning score on a 17-yard touchdown pass with five seconds left.

Hours later, Ortiz hit a game-tying grand slam with two outs in the bottom of the eighth inning, giving the Red Sox life in a series they eventually won in six games before taking the World Series.

Ortiz would win three World Series in his Red Sox career, while Brady won six Super Bowls with the Patriots. The two became the most beloved sports stars in a generation, taking their place alongside Bobby Orr, Bill Russell, Carl Yastrzemski and Larry Bird.

And so Brady was just as shocked as everyone else in 2019, when Ortiz, three years removed from retirement and back home in the Dominican Republic, was shot by an unknown assailant at a restaurant. Brady was among the first to send the message that he was praying for his friend.

Papi could do no wrong in Boston, except when it came to convincing Brady to stay

Ortiz would soon return to full health, but in 2020, after the Patriots lost their Divisional Round NFL Playoff game to the Tennessee Titans, hearts across New England began to break.

Tom Brady, the GOAT, was an unrestricted free agent, and all indications were that he was not coming back to the Patriots after 19 seasons.

No one was more shocked and determined not to let go than David Ortiz.

“There’s two things you’re never going to waste with Tom Brady: That’s time and money,” Ortiz said in an interview with NBC Boston. “This guy is money and this guy gives you the best effort.”

In 2016, Brady had playfully tried to talk Ortiz out of retirement, posting a picture of himself on his Facebook page, imitating Ortiz’s signature sky point after a home run, and implored his and Ortiz’s fans to donate to Ortiz’s children’s charity.

Brady then added this line:

“PS – It’s not too late to change your mind, Papi!! Let’s talk…. HA”

Now, three years later, it was Ortiz trying to keep Brady from leaving New England.

I don’t want him to go anywhere. I want him to stay,” Ortiz told Boston radio station WEEI. “That’s my mind. But it’s up to whatever is best for him and his family. It’s not all about what people think. He has a choice what is good for him. It’s not just for people telling him what he has to do. I hope he stays with the Patriots, but it’s not up to what I say. It’s his decision.”

The decision was to go to Tampa Bay. For one very rare time, Big Papi could not save Boston from a devastating loss.

Stats courtesy of Pro Football Reference

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