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Who Takes The Greatest Play in Red Sox Modern History? Roberts, Ortiz, or Benintendi?

Every championship has a signature play. In 2004 it was Dave Roberts’ steal. In 2007, it was JD Drew’s grand slam. In 2013, it was David Ortiz’s grand slam. In 2018, it was Andrew Benintendi’s game-saving diving catch. So among these heroic plays, who holds the title? They’re three entirely different plays using 3 entirely different skillsets in 3 entirely different positions in the game and series.  Apologies to J.D. Drew, who I’m going to underrate again, and the 2007 Red Sox, who will once again be the forgotten championship, but it’s not even the best grand slam on the list.

The Moment

Roberts’ Steal:

Game 4 of the ALCS, down 3-0 in the series, and down 4-3 in the game. Dave Roberts on first, 0 outs, Bill Mueller at the plate. Against the Yankees with an 86 year curse. 

Papi’s Grand Slam:

Game 2 of the ALCS, down 1-0 in the series, and down 5-1 in the game. Bases loaded, 2 outs, David Ortiz at the plate. 

Benintendi’s Catch:

Game 4 of the ALCS, up 2-1 in the series, and up 8-6 in the game. Bases loaded, 2 outs, Alex Bregman at the plate.

All of these are obviously nail-biting, crowd standing, all or nothing moments. Interestingly, they all happened in the first pitch of the at-bat. I don’t think one exactly stands out in terms of the greatest moment. That said, Roberts’ steal was on the actual brink of elimination. Down 2-0 in the series heading to Detroit would have been really tough, but they in theory still could have lost that game and still gone to Game 7 if the rest of the results held up. In a worst-case scenario in 2018, and that ball gets by Benintendi to the wall, scoring all 3 runs, they are still tied 2-2 in the series with home-field advantage. For the Sox, Game 4 was it. 

Edge: Roberts.

The Skill

Roberts’ Steal:

Stealing second with an entire curse on your shoulders when the entire world knows you’re going. 

Papi’s Grand Slam:

A home run off of a bad changeup in an unbelievably clutch situation.

Benintendi’s Catch:

An all-or-nothing diving catch off of a sinking liner.

I don’t mean to compromise the Papi slam, but he did that 557 other times in his career. The situation is what made it great, not the actual skill of capitalizing on a bad changeup from a right-handed pitcher. That brings us down to Roberts and Benintendi. For Roberts, the play at second was incredibly close and was correctly called safe. If his jump is a microsecond late, he’s out, so getting the perfect jump in such a situation is quite impressive. Plus the dive into the outside corner of second base was the reason he was safe. If he messes that up, he’s out. So little room for error. For Benintendi, the jump was key for him too. If he’s a microsecond late, he might not get to that ball in time and lets it drop in. The catch itself, and the actual decision to dive is what separates Benintendi here. The decision to put it all on the line, and the focus on the ball to actually catch the ball as it falls to the ground is unbelievable, especially in such a situation.

Edge: Benintendi

The Importance

Roberts’ Steal:

It might have kept the door open for the Sox, giving them only the need for a base hit from any of the next 3 batters to tie the game and keep their season alive.

Papi’s Grand Slam:

One swing of the bat got the Red Sox back in the series, tying Game 2 and putting and what was a lifeless team just a couple of minutes before on the verge of tying the ALCS.

Benintendi’s Catch:

It saved Game 4 in Houston to, somewhat shockingly, put the Sox up 3-1 in the series over the defending champs*. 

Who knows, the Sox may not win any of the 3 World Series if not for these plays, that’s why they’re so iconic. Roberts’ steal could have all been for naught if the Sox had lost extra innings in Game 4. Or Game 5. Or 6 or 7 for that matter. There are so many scenarios where that steal means nothing. If he’s out, the Sox have 2 outs to work with, albeit against Mariano Rivera, but it’s possible. Papi tied the series and injected life into the Sox. They had been held scoreless through the first 14 and ⅔ innings of the series on just 1 hit before a 6th inning run and the eventual 8th inning rally. It’s really tough to see the Sox winning that series if Ortiz strikes out and they go on to lose that game 5-1. Benintendi won an entire crucial game. If the Sox lose that game, they’re tied, but I have confidence that one of the best teams in baseball history could win 2 of 3.

Edge: Papi

This is the part of the article where I acknowledge that I have no idea what the who is leading

The Opposite Outcome

Roberts’ Steal:

He’s out at second, leaving Bill Mueller at the plate with 1 out and nobody on against Mariano Rivera, with Mark Bellhorn (or maybe Doug Mientkiewicz) and Johnny Damon due up. Chances are, they don’t score and are embarrassingly swept by the Yankees. The entire future of the Red Sox changes.

Papi’s Grand Slam:

Ortiz gets out, leaving the Sox down 4 runs heading to the ninth with Mike Napoli, Johnny Gomes, and Jarrod Saltalamacchia due up.

Benintendi’s Catch:

There are a couple here. Maybe Benintendi plays it safe or traps the ball, 2 runs score, and the game is tied 8-8 with runners on first and third with 2 outs for George Springer. If Benintendi still dives and the ball gets by him to the wall, more than likely all three runners score and the Astros win the game, tying the series at 2. 

We’re judging this by how screwed they would have been if the heroics didn’t happen. We can rule out Benintendi here. If the Sox lost Game 4 in Houston, they’re still in a good spot. Again, no room for error for Roberts makes him hard to avoid here. Scoring a run with one out to spare against Rivera. Coming into the inning, the Red Sox had a 24.5% chance of winning the game. That was with 0 outs in the inning. With 1 out, it would likely be in single digits. However, as mentioned, even though the Sox went on to win games 3, 5 and 6 against Detroit, I find it really tough to believe those results would hold if they don’t win game 2 in the dramatic fashion that they did. 

Edge: It’s a toss up between Roberts and Ortiz here.

That didn’t help

Position to Win

Roberts’ Steal:

They still needed to get Roberts to cross the plate. And then win Game 4, and 5, 6, and 7. And then the World Series (spoiler, they did it all in a row).  

Papi’s Grand Slam:

Papi’s slam tied it, but they still needed to win Game 2 which was then a tie game going into the 9th, then still win 7 more games to win it all (another spoiler, they did it).

Benintendi’s Catch:

The catch won the game. They had a stranglehold on the Astros and then had to win 5 more games to win the think (final spoiler, they also did it)

We’re judging this by how much each play put the Sox in a position to win. Roberts and Ortiz turned the game 180 degrees, but Benintendi saved that from happening in the reverse sense. Again, Roberts’ steal is forgotten if they lose Game 4 in extras or any of the following games in the ALCS. Game 4 changed the vibe of the series despite it being 3-1, but they still had a lot of work to do. Same thing in 2013, the Sox didn’t hit very much in that series, but they did when they needed to. They still had to beat Justin Verlander, Anibal Sanchez, and Max Scherzer. When Benintendi made that catch, the series felt locked up. It wasn’t, but going into Houston and taking both games on the road against the defending champs* was a heck of a statement. If they lose that game, they’re still in a decent spot, but it’s a completely different series that’s then guaranteed to head back to Fenway for a Game 6 against an injured Chris Sale. 

Edge: Benintendi. 


Roberts’ Steal:

“Alright, we’re not dead yet”

Papi’s Grand Slam:

“Oh my god. There is no way that just happened”

Benintendi’s Catch:


This is stupid, but it adds to the moment. The Benintendi catch I think you can relate to a hockey goal, where you see the ball go into his glove after a second of suspense and immediately just jump up and scream, just like Benny himself did. Trust me, I woke up the house at 1 am when it happened. The Roberts steal was more of a sign of relief than something to actually celebrate because there was more work to do. The Papi slam was just disbelief. Coming into the situation, you dream that he hits the grand slam, but you don’t actually think it’s going to happen. Then when it does, it’s just shock. Adding to the fact that it was David Ortiz, already the greatest clutch hitter in franchise history, it’s just truly unbelievable.

Edge: Papi.

Now I’m improvising and adding sections to try and convince myself


Roberts’ Steal:

It’s treated like the play that won them the World Series. It didn’t, but it might have. Who knows. Regardless, it’s the signature play from the greatest comeback in sports history.

Papi’s Grand Slam:

Maybe the greatest clutch highlight of one of the greatest clutch hitters in MLB history. Maybe – he helped cement Roberts’ legacy too.

Benintendi’s Catch:

It’s probably, but not obviously the highlight of the 2018 playoffs. The highlight of the season was Mookie Betts’ 13 pitch grand slam, and the 119 wins that the Sox accumulated that season overshadowed the heroics of Benintendi’s catch

Dave Roberts is known for one thing and one thing only as a player: the steal. David Ortiz has countless moments toward his legacy. Andrew Benintendi still has lots of time to cement his legacy. The 2018 Sox have become more remembered for dominating the league and winning the World Series pretty much uncontested, so the catch has become a bit underrated in terms of just how important it was. Oddly, if Papi’s grand slam was his only career moment, it would probably hold more weight, but there are just so many moments with Big Papi that you have to consider. Also, when you think of the 2013 Sox, the first thing you think of is the marathon bombings, Papi’s speech, and maybe even Daniel Nava’s home run. Roberts’ steal has lived the longest and is the most iconic. He even got a standing ovation from the Fenway crowd as the opposing manager in the World Series 14 years after it happened. 

Edge: Roberts


Roberts’ Steal:

The Moment, The Opposite Outcome, The Legacy

Papi’s Grand Slam:

The Importance, The Opposite Outcome, The Reaction

Benintendi’s Catch:

The Skill, Position to win

I give up. I have no idea. I’d probably lean toward the Benintendi catch being last simply because the ALCS would still have been tied at 2 if the Sox lost Game 4, but the catch was also had the most skill in a baseball play of them all. Roberts had zero room error on his steal, and it kept the Sox alive, but they still had so much work to do, and with one wrong bounce the Roberts steal was forgotten forever. And Papi, seizing the moment like no other, the most clutch player in Red Sox history. 

Screw it, I’m going Papi for the greatest play in modern-day Red Sox history, but the other two are not far behind.

Top Image of Benintendi: John Glaser, USA Today

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