The fact that the Yankees have a vitally important three-game set coming up this weekend at Fenway Park should not come as news to any diehard fans. Honestly, it’s probably been on most folks’ calendars for months now, ever since it became apparent early on that the Red Sox had quickly rebounded to put their 2020 irrelevancy behind them. As the last Yankees/Red Sox series of the regular season, this was bound to be a big one, and the Wild Card implications only make every pitch somehow feel even more impactful. Hell, if the season ended today, the Wild Card Game would be this exact matchup at the same locale: Fenway Park.

I’m getting ahead of myself, though. There are nine games down the stretch to determine which of the Yankees, Red Sox, and Blue Jays (and I guess Mariners) will nab the two Wild Card spots. Clutch performances from the Yankees’ bats would come in handy right about now. To psych ourselves up about the possibility, I thought that it would be fun to look back on the Yankees’ longest homers at Fenway since Statcast began tracking them in 2015. The “Statcast Era” tag always mildly amused me, but calling it the “Baby Bomber Era” feels more appropriate since that was when we first caught a glimpse of the Yankees’ future.

So here they are: the Yankees’ most titanic Fenway Park blasts of the Baby Bomber Era.

1. Gary Sánchez (479 ft.)

October 6, 2018

This was a helluva shot by El Gary off Eduardo Rodriguez — the third-longest hit by any player in the postseason since 2015 — and was in the mix for the most important homer of the Yankees’ 2018 season. It put some distance between them and the Red Sox in Game 2 of the ALDS, allowing New York to slam the door and take home-field advantage away from the 108-win Boston juggernaut. As for what they actually did with that home-field advantage? Ask someone else, as I have removed it from my brain à la “Eternal Sunshine of the Spotless Mind.”

2 (tie). Gary Sánchez (446 ft.)

September 28, 2018

There’s that man again. The stakes weren’t as high at Fenway as they would be a week later during the Division Series, but a tape-measure shot is a tape-measure shot. Sánchez’s solo homer against lefty Brian Johnson put the Yankees the board en route to an 11-6 victory, their 99th of the 2018 campaign.

Aaron Judge and Giancarlo Stanton get most of the attention, but Gary can absolutely hit dingers just as far.

2 (tie). Austin Romine (446 ft.)

July 28, 2019

Yes, I blinked twice as well. It wouldn’t have surprised me to see a third homer by a Yankees catcher on this list, but it does surprise me to see it off the bat of Romine instead of El Gary.

Sánchez’s former backup has only hit 28 homers in 428 games across 10 big league seasons, but on this occasion, he muscled up off no less a menace on the mound than perennial All-Star Chris Sale. Sure, this was an off-year from the lefty and he had Tommy John surgery the following spring, but still — this was quite the blow from Romine and the longest of his career. The Yankees won, 9-6, during a year in which they did successfully beat Boston and Tampa Bay out for the AL East crown.

4. Aaron Judge (445 ft.)

October 6, 2018

I suppose it took Judge long enough to show up, huh? This clout off David Price came in the same game as the aforementioned 479-foot Sánchez shot. It’s one of 17 homers in Judge’s six-year career that have sailed at least 445 feet.

The drive also put the Yankees on the board in the first as they quickly responded to their ALDS Game 1 defeat with an early lead that they never relinquished. Again, it’s just a shame that Judge’s troll job after the game backfired.

5. Aaron Judge (444 ft.)

April 10, 2018

Two Judge homers on this list makes a lot of sense. This one doesn’t need much said about it since it came in the middle of a miserable 14-1 defeat, but at least it was another one off Sale, I suppose.

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The only upset here from this quintet of monster shots is that Stanton didn’t make the cut. He’s actually only homered at Fenway twice in pinstripes, though one did go 432 feet. Maybe this weekend will finally be the time for him to top 440 at Fenway. It just takes one poorly-placed pitch to someone that strong.

Speaking of strong gentlemen though, below is a brief salute to another muscle man who came a foot short of the cut.

Honorable Mention: Matt Holliday (443 ft.)

July 15, 2017

Holliday is now a somewhat-forgotten fella in the story of the 2017 Yankees’ resurgence, but for a good while, he held down the DH position with some key long balls. This missile was his second-biggest homer of the season after an April walk-off against the Orioles, and it came off an even tougher foe. Craig Kimbrel hadn’t blown a save at home in a year and a half as the Red Sox closer, but Holliday obliterated this offering to shatter Boston’s hopes of a 1-0 victory. Although it took 16 innings, the Yankees prevailed, 4-1.

9/26 Update

Due to his absurd weekend series against the Red Sox, Giancarlo Stanton now ranks No. 2 & No. 3 on this list, thanks to this 452-footer on Saturday ...

... and this 448-footer on Sunday:

I, for one, will always dare that man to hit even longer dingers in the future.