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DraftKings Sportsbook is Coming Soon to Massachusetts: Jared Carrabis Ranks the Top Five Red Sox Postseason Games He Has Attended

In honor of DraftKings Sportsbook coming to Massachusetts soon, Jared Carrabis highlights his best experiences at Red Sox playoff games!

ALDS: Los Angeles Angels v Boston Red Sox, Game 2 Photo by Jim Rogash/Getty Images

Rejoice, Red Sox, Patriots, Celtics, Bruins fans and everyone in between! The state of Massachusetts is approving mobile sports betting and DraftKings Sportsbook will soon be available for residents. The launch date for the DraftKings Sportsbook App is Friday, March 10.

In honor of the Massachusetts launch, we have been reliving some of the biggest sports moments in state history. This time around, I’m going to highlight the best Red Sox postseason games I’ve personally attended.


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Check out the Jared Carrabis Podcast on the DraftKings Youtube Channel and the official Jared Carrabis Youtube Channel. You can also subscribe on Apple Podcasts and Spotify. Follow the show on Twitter @carrabispod.

The Top Five Red Sox Postseason Games I’ve Ever Been To

*cracks knuckles* Okay, let’s see if I remember how to do this. Writing has always been my passion, and I’ve been away from it for far too long. With sports betting finally getting the green light here in Massachusetts, I figured it was the perfect time to get back at it by breaking down the best Red Sox postseason games I’ve ever been to.

Before we get into it, I just want it on the record that it was incredibly hard to narrow it down to just five. And then once it was narrowed down to five, it was even more difficult to actually rank them. People think it’s easy being a Red Sox fan blessed with so many memorable experiences in October. It’s not. I’ll have you know that I’ve got a lifetime record of 12-6 in the postseason. Some would say those are Hall of Fame numbers. Not for me to say, but some are saying it. I’ve been to at least one playoff game in each of Boston’s four championship seasons since 2004, so I tried to have all four runs represented here. Let’s just say I’ve been pretty damn lucky with some of the games I’ve been in attendance for. Without further ado, let’s get to it.

5.) 2007 ALDS Game 2 — Red Sox win 6-3

ALDS: Los Angeles Angels v Boston Red Sox, Game 2 Photo by Jim Rogash/Getty Images

So, some of these games will make the list for their defining memorable moments more so than the game itself in its entirety. To this day, people still pose as Manny Ramirez did at home plate when he launched a walk-off homer deep into the October night against K-Rod in Game 2 of the 2007 American League Division Series. Chris Sale actually just did this at Red Sox Winter Weekend when a fan asked the lefty who his favorite Red Sox player was from the 2004 World Series team. He just stood up, put his arms in the air, and everyone knew who he was talking about just from the pose alone.

The 2007 World Series team never really gets the love it deserves, but it’s understandable why. When you, as a fan base, have not won a World Series in 86 years and then you finally win one…let’s just say you’re not prepared for a second one only three years later. I know I wasn’t. Quite literally, I was still riding the high of 2004 when 2007 rolled around. I started my Red Sox blog as a junior in high school on New Years Day 2006. The Red Sox fan base was still buzzing from 2004, which essentially helped launch my career. And then when 2007 happened, it strapped a rocket to my ass as an 18-year-old who was a month into his freshman year of college.

2007 was also the year that I ran for President of Red Sox Nation, got beat out by the legend Jerry Remy, ultimately finishing in third place. As a gift from the team for participating in the election, they gave me tickets to Game 2 of the ALDS. As I had done for my entire life to that point, I went with my dad. I couldn’t tell you much of what happened during that game, but I can tell you that I can still see the ball in flight off of Manny’s bat from my point of view that night when he connected for that walk-off homer. It just went up into the lights and then disappeared into the black sky. I actually have a bobblehead of Manny doing the hands up pose. One of the most iconic pictures in Boston’s sports history is the shot from the third base side showing Manny with his hands up, but you can see the sold out crowd at Fenway Park all doing the same exact pose that Manny did, almost as if it was choreographed.

4.) 2018 World Series Game 3 — Red Sox lose 3-2 (18 innings)

Yes, I have a loss on my list. If you watched that game live, then you know why. I knew that I had to include a 2018 postseason game on this list, and there were some good ones that I was at, including the World Series clincher. But when I think back on that run, I think of the 16-1 ass beating that the Red Sox handed the Yankees at Yankee Stadium, I think of Chris Sale mowing down the Dodgers in order to clinch the series, and I think of Nathan Eovaldi’s performance out of the bullpen in extra innings against the Dodgers in LA. It was an 18-inning marathon that had diehard fans feeling like they were out there playing a doubleheader with no break, too.

The Red Sox had themselves a 2-0 series lead after taking the first two games in Boston, but momentum can change in an instant in the postseason. Boston was trailing 1-0 in the 8th inning when Dave Roberts dialed up his closer Kenley Jansen, who got the first two batters he faced before Jackie Bradley Jr. came to the plate. That’s ALCS MVP Jackie Bradley Jr. to you. The Red Sox centerfielder wasn’t on some sort of heater that postseason, but he picked his spots to deliver about as best as any postseason performer ever has. With a 2-0 count, Jansen left one out over the plate and Bradley launched it into the seats in right to tie the game. In the top of the 13th, Brock Holt scored from first when the ball got away on an infield single by Eduardo Nunez. It was looking like the Red Sox were about to put a stranglehold on the series with a 3-0 lead.

Eovaldi had entered the game in the bottom of the 12th, so he was in line for the win if he could shut down the Dodgers in the bottom of the 13th. Easier said than done. With a runner on second, Yasiel Puig hit a stinger up the middle that was backhanded by Ian Kinsler, who made a throw that wasn’t even in the same area code as first base. The ball got by eventual World Series MVP Steve Pearce, and we were tied once again.

Nathan Eovaldi pitched his balls off, logging six scoreless frames in extras before Max Muncy got him for a leadoff walk-off homer in the bottom of the 18th. Now, you may be sitting there wondering why this game would’ve made the list if the Red Sox lost. Well, it was in that visitor’s clubhouse after this loss that the Red Sox decided that they would not lose another game. Eovaldi was applauded by his teammates for going out there and shoving for his team. His teammates would not allow him to hang his head in defeat. That group came together in that moment and knew that they were going to pick up their guy who just left it all out there for them in the World Series. And they did. The Red Sox went on to win Game 4 and 5, capturing their fourth World Series title in 15 years. It was one of the gutsiest performances in postseason history, and it was amazing to have seen it in person, all seven hours and 20 minutes of it.

3.) 2008 ALCS Game 5 — Red Sox win 8-7

Tampa Bay Rays v Boston Red Sox, Game 5 Photo by Jim McIsaac/Getty Images

Nobody remembers this game. It sounds arrogant, but it’s easy to forget games during postseason runs that don’t end in a championship when you’ve seen four of them. The Red Sox did not win the World Series in 2008. I maintain that if Josh Beckett and Mike Lowell were healthy, the Red Sox would’ve been the first team to go back-to-back since the Yankees in 1998, 1999, and 2000. In his book, Terry Francona called the 2008 Boston Red Sox the best team that he managed during his tenure here. This was the same man who was at the helm for two championship seasons in 2004 and 2007.

On this night, a friend of mine invited me to the game. He did not show up to said game. The Red Sox were trailing in this series three games to one at the time, facing elimination at home after winning Game 1 of the series in Tampa against the Rays. Here I am, as diehard of a Red Sox fan as diehard gets, suffering in silence, alone, watching my season come crashing down around me. The Red Sox were losing seven to nothing in the seventh inning. It was over. I don’t handle losing well. I don’t handle the offseason well. I get really sad. When the Red Sox were down seven-zip, I remember getting into an argument with my, then, girlfriend and just ended the relationship because I was in a downward spiral over the Red Sox getting eliminated in such an abrupt and embarrassing fashion. Yeah, I just can’t do this anymore.

Then the bottom of the seventh happened. An RBI knock for Dustin Pedroia, and a three-run bomb for David Ortiz and we are back in business. Still single at the time, though. Then we go to the bottom of the 8th, and it’s a two-run bomb for JD Drew and an RBI knock for Coco Crisp. It’s 7-7 and Fenway Park is going NUTS. Justin Masterson shuts Tampa down in the top of the 9th, setting the stage once again for Drew. He’s up there with two outs and Kevin Youkilis standing at second base. Fenway’s vibrating. 3-1 count. Everyone’s on their feet. Drew hammers a liner to deep right over the head of Gabe Gross and we are going to Tampa!

It still kills me that that team didn’t go all the way. Such a special team. Such a special game. Down 7-0 in the seventh inning, and they came all the way back and won. Not only did they win that game, but they even forced a Game 7 in which they held a lead in. For those wondering, yes, I did patch things up with the girlfriend after the game. She understood that I was just a psychopath because of the Red Sox. That comes with the territory, unfortunately.

Check out the Baseball Is Dead Podcast on the official Jared Carrabis Youtube Channel. You can also subscribe on Apple Podcasts and Spotify. Follow the show on Twitter @baseballisdead_.

2.) 2013 World Series Game 6 — Red Sox win 6-1

This is another one of those games where the game itself didn’t matter. It was about the moment. The moment when the Red Sox won the World Series at Fenway Park for the first time in 95 years. The moment when the Red Sox completed their magical season after the tragic events of the Boston Marathon bombing. The moment when a city needed an outlet for healing, and then they got an entire season’s worth of them that culminated in a championship just a few miles down the road from where that tragedy took place. I will never forget that moment.

That team was not supposed to win the World Series. It was an island of misfit toys, who came into spring training camp, grew their beards out, blocked out the noise, and came together for one common goal. Before the World Series started, I had made my TV debut on NECN doing live hits outside of Fenway Park before each World Series game. Before Game 1, I was asked for my prediction. “Sox in 6,” I said. When the Red Sox had a chance to clinch the World Series on the night of Game 6, my mom told me, “You have to be there.” I was working a part-time job. I didn’t have the money for World Series tickets.

That’s when I emailed, now, Red Sox President and CEO Sam Kennedy. I said, I know you’re probably getting a million requests for tickets right now, but if you have any tickets for tonight, I’ve got a credit card ready to go. He didn’t need to know it was my mom’s. He got back to me and told me he had two standing room tickets waiting for me. I was elated. I remember getting to Fenway absurdly early, waiting in line at will call when nobody was even there yet, grabbing the tickets and quite literally sprinting to a standing room spot that I had already picked out in my head before we had even gotten in the car. I knew it was every man for himself as it pertains to standing room only, especially on the night that the Red Sox could clinch a World Series title at home for the first time in 95 years.

As the story goes, I didn’t even look at the actual tickets until after I had gotten back home from the game. They were Green Monster standing tickets. Whoops! We ended up somewhere high above the third baseline. For the final out, I stood on top of the ledge meant for placing hot dogs and beer and grabbed onto a pipe above my head, took out my cell phone and recorded the final out of this magical championship. The video was then used in the Red Sox World Series DVD narrated by Kevin Millar! That was pretty cool.

I’ve had season tickets at Fenway Park since 1998 in Section 10. It was a little weird for me, at that point, to watch a Red Sox game anywhere else. After the final out and the trophy presentation, my mom and I went to our seats in Section 10 and I sat in the same seat that I’ve been sitting in at Fenway Park since I was nine years old, and I cried. I’m not an emotional guy by any means, but you put me in the seats for a Red Sox World Series and I will cry like a baby. It was such an emotional year. It meant the world to me that I got to have that memory with my mom, and I just couldn’t hold it in when we got to our seats. Yeah, it was the third one. Yeah, they had just won one six years before that. But I don’t think anyone could truly understand what that championship meant to the city of Boston unless you called that place home.

1.) 2004 ALCS Game 4 — Red Sox win 6-4 (12 innings)

American League Championship Series - New York Yankees vs Boston Red Sox - Game 4 Photo by Jim Rogash/WireImage

This was the best game ever played at Fenway Park. Period. No game will ever dethrone Game 4 of the 2004 ALCS at Fenway Park.

You all know the story. Just one year prior, the Red Sox and their fans had their hearts ripped out by Aaron Boone when he launched a walk-off home run into left field corner in Game 7 of the ALCS at Yankee Stadium to send the Yankees to the World Series. Again. I cried after that one, too. Yeah, because they lost. But let’s throw in the wrinkle that I had tickets to Game 1 of the 2003 World Series with my dad. They were five outs away. I wanted that moment so badly. I wanted it for my dad more than I wanted it for me. Heartbreaking isn’t even the word. I was devastated.

Fast forward a year later, and I’m at Fenway Park with my dad, only this time the Red Sox are staring a 3-0 deficit in the face to the very same Yankees. This game was littered with all-time legendary Red Sox moments, but what I’ll remember most is the crowd. They were angry. And you could feel it. It was palpable. That’s why this game can never be beat. You can’t replicate that emotion and I’ll tell you why. This was 86 years of frustration. This was a year after the Aaron Boone home run. This was coming off the offseason in which the Red Sox went out and signed Keith Foulke and traded for Curt Schilling to reload in hopes of taking down the Yankees and finally end an 86-year championship drought. All of that just to get dusted by the Yankees and not even put up a fight in the ALCS. But then things changed.

In the bottom of the ninth, the bullpen gate opened and out comes the literal greatest closer who ever lived, Mariano Rivera. If you weren’t feeling great going into this game down three-nothing, then you certainly weren’t feeling much better seeing Mo jog out to the mound with a one-run lead in a game that, if he records the save, the Yankees go back to the World Series, a place that he was quite familiar with having been there six times already by that time. Logic would tell you that this game is over. But then your mind starts computing numbers and scenarios, and you’re like…wait a second. If Kevin Millar gets on somehow, then Francona can go to Dave Roberts off the bench to get some speed on the bases. If Roberts can swipe a bag here, then he’d be in scoring position for Bill Mueller. Yes, the same Bill Mueller who hit a walk-off bomb off Rivera back in July in that legendary game that Jason Varitek whooped up on A-Rod. But what are the odds of THAT happening?

I’ve seen many walk-off homers in my day. The crowd pop when Roberts was called safe was louder than just about all of them. It was deafening. The rest, as they say, is history. How important was that stolen base, you ask? In Boston, all you have to say is “The Steal” and people know exactly which one you’re talking about. You don’t have to say Roberts’ name. You don’t have to mention 2004 or the ALCS. Just two words — the steal. Say less.

I’ve rewatched that game so many times that I can press play in my brain and hear Joe Buck’s call without needing reference. “Up the middle! Roberts will come to the plate! The throw by Williams! Bill Mueller has tied it!” If there was a roof on Fenway Park, we would’ve blown the roof off that place. It was mayhem. I couldn’t believe it. I mean, I could. But I couldn’t. I still can’t. What’s that old statistic? More men have walked on the moon than have scored against Mariano Rivera in the postseason? This man has 141 innings in the postseason. That’s almost a full season for a starting pitcher. What took place that night in front of my very eyes was almost a mathematical impossibility. But it happened. It really happened.

The Red Sox deployed their whole bullpen in an effort to keep the Yankees from scoring. Alan Embree, Mike Myers, and Curtis Leskanic. Guys who, let’s face it, were nowhere near Mariano Rivera status. Nobody was. But they got the job done. On to the bottom of the 12th where Manny Ramirez started things off with a base hit. Then you could feel the rumble throughout the crowd, because here comes David Ortiz. It was like you could hear the Jaws theme in your head without it even playing out loud. Big Papi built his entire legacy in the month of October, and he was about to add to his resume by hammering a two-run walk-off tank into the Yankees’ bullpen. Suck on that.

I remember standing on my seat and losing my mind. We didn’t leave for what felt like forever. Nobody wanted to go home. I don’t know what it was, because we were still down 3-1 in the series, but it was more or less what Kevin Millar was saying before the game. Don’t let us win tonight. Because then you’ve got Pedro in Game 5, Schilling in Game 6, and then Game 7…anything can happen. And it did.

That victory was the first of eight straight for the Red Sox en route to their first World Series title in 86 years. They didn’t lose another game after that night. You already knew that, but it feels nice to say it out loud again. The Red Sox came all the way back from being down 3-0, completing the greatest comeback in the history of the sport, becoming the only team to ever come back to win a best of seven series after being down 3-0, by blowing the Yankees’ doors off in Game 7 at Yankee Stadium before sweeping the St. Louis Cardinals in the World Series. The 105-win Cardinals never even had a lead in that World Series. Not even for an inning. I will never forget that night for as long as I live. The greatest game ever played at Fenway Park. And I was there.

Honorable mentions:

Some honorable mentions here — as previously stated, I was in LA when the Red Sox clinched the 2018 World Series title. Cried for that one, too, and then somehow found myself on a duck boat for the World Series parade. Best day of my life. I was at Yankee Stadium in 2018 for Game 4 of the ALDS when the Red Sox eliminated the Yankees, and that might’ve been the loudest stadium I’ve ever been in when New York was mounting a comeback in the ninth inning. So much so that the gentleman behind me tapped me on my shoulder and let me know that he “had my back incase anything goes down.” Yeah, that’s how rowdy it got. They wanted me dead. I was at both of the walk-off wins against the Rays in the 2021 ALDS. That was such a fun year, too. I really wish that team went all the way. Such an awesome group of players on that roster. Season ended too soon. I was at Game 1 of the 2007 World Series where Josh Beckett dominated and the Red Sox pounded the Rockies 13-1, so my dad and I finally did get our Game 1 of the World Series together after all. And finally, I was at Game 2 of the ALDS in 2013 when David Ortiz hit two bombs off David Price, which ultimately led to Price throwing at Ortiz the following season before they became best friends in 2016 when I recruited Price to the Red Sox. It’s true. Look it up.

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