Alex Rodriguez Drilling Among Will Middlebrooks’ Favorite Red Sox-Yankees Memories

Sox Talk with Will Middlebrooks is a recurring content series on NESN.com. Middlebrooks, a former Red Sox player and current NESN analyst, gives his insight and opinion on pertinent Red Sox storylines throughout the season. You can read the latest stories from the series here.

Will Middlebrooks, who played for the Boston Red Sox from 2012-14, wasn’t directly involved in the play.

But what unfolded when superstar Alex Rodriguez stepped into the batter’s box against Ryan Dempster at Fenway Park nearly a decade ago still stands out in the mind of Middlebrooks when he thinks about his favorite memories of when he was a part of the fierce Red Sox-New York Yankees rivalry.

Dempster started the at-bat against Rodriguez, who was in the middle of appealing his 211-game suspension for performance-enhancing drug use, by throwing behind the Yankees infielder before drilling Rodriguez with a 3-0 fastball.

Rodriguez didn’t offer much of a reaction after getting plunked, but the same can’t be said about then-Yankees manager Joe Girardi. Girardi, who bolted out of the dugout, was incensed that Dempster only received a warning from home-plate umpire Brian O’Nora, and Girardi even threw his hat in a fit of rage.

Rodriguez let his bat do his talking for the rest of the game as he responded by going 3-for-4 with a home run and two RBIs.

“I was playing third base when Dempster drilled A-Rod,” Middlebrooks told NESN.com as the Red Sox face the Yankees for the first time in the 2024 season Friday night at Fenway. “It didn’t really clear benches. Guys came out but they didn’t come on the field. But Girardi lost his mind. We’re all just standing behind the mound watching him lose his mind and A-Rod goes to first. And then he comes up later in the game and takes Dempster deep to center. Gets to home plate and does the Big Papi celebration at home plate.

“We had a team full of like degenerates who probably wouldn’t have ripped him to pieces. But it was also guys like Ryan Dempster who was like, ‘You know what, I’m drilling him because I feel like I’m doing that for baseball.’ That was fun.”

Middlebrooks was much more involved in a four-game series on the road against the Yankees three weeks later.

Middlebrooks hit a home run in each of the first two games of the series, including belting a 435-foot blast off Ivan Nova and taking Andy Pettitte deep the next day.

There was still one more long ball left in Middlebrooks’ bat for the series and he saved it for when he faced Mariano Rivera in the finale of the four-game set. Middlebrooks hit a homer off the legendary Yankees closer in the top of the ninth to level the score — New York walked things off in the bottom half of the inning — and it ended up being the last home run Rivera gave up in his storied career.

“That’s my claim to fame is being the last guy to take Mariano deep,” Middlebrooks said.

Middlebrooks only spent three seasons with Boston, but he cherished his time playing against the Yankees in a Red Sox uniform. The heated rivalry afforded Middlebrooks the opportunity to face Yankees greats like Rodriguez and Rivera along with Derek Jeter, Mark Teixeira and C.C. Sabathia.

And that alone was memorable for Middlebrooks.

“Just being able to see the Yankees legends come through there and compete against them,” Middlebrooks said. “Obviously to beat them was even better. But just to be on the same field as a lot of those guys was pretty cool.”