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What are Syracuse’s biggest ‘rip your heart out’ moments?

One particular gut punch comes to mind right off the bat...

NCAA Basketball: NCAA Tournament-Second Round- Michigan State Spartans vs Syracuse Orange Rick Osentoski-USA TODAY Sports

On Thursday morning, CBS Sports/ESPN U Radio’s Barrett Sallee asked a question about teams’ biggest “rip your heart out moments,” prompted by last night’s College World Series result — an Oregon State comeback over Arkansas to force game three.

Now, as Syracuse Orange fans, we’re very familiar with this sort of loss. We have wins to balance these heartaches out in a lot of cases. But still, our fandom is largely defined by the times we came up just short, save the one time we most certainly did not.

But which are the biggest gut punch losses for the Orange? The list has an obvious starting point, though the order of the rest is probably up for a little more debate....

(and I’m leaving off lacrosse, not because we don’t have these sorts of moments, but because there are more than enough positives to completely block them out)

1. Keith (EFFING) Smart

Zero debate. With Syracuse up 73-72 on Indiana in the 1987 National Title Game, Derrick Coleman missed the front end of a one-and-one, and then Keith Smart hit a corner jumper with five seconds left for the go-ahead points. The Hoosiers won 74-73 and the haunting fact of “never winning the big one” would follow Jim Boeheim and the program around for another 16 years until they returned to New Orleans with luck (and talent) on their side en route to a championship. Still, Keith (Effing) Smart, man...

2, 2013 Final Four

Syracuse held their own against favored Michigan, and was down just two (58-56) with 19 seconds to go and driving toward a potential tie (or even the lead). And then... the charge. The Orange would fall 61-56, a result we’re all still a little bitter about. I remember getting very angry at an obnoxious, fair-weather Wolverines fan at a bar in Long Beach, Calif. It was not a pleasant evening.

3. Lawrence Moten’s timeout

Just two years after Chris Webber’s infamous, erroneous timeout call, the Orangemen had their own similar moment as Moten called for one with three seconds left and a one-point lead versus Arkansas in the 1995 NCAA Tournament. The Razorbacks would get to overtime and win by two. Ugh.

4. Kendall Gill’s rebound over Derrick Coleman

This one isn’t talked about as much as the others, but it’s still a damaging defeat. An incredibly talented Orangemen squad was down just 87-86 to Illinois in the 1989 Elite Eight after a three-pointer from Sherman Douglas. A missed foul shot with 20 seconds left was Derrick Coleman’s for the taking, but Kendall Gill managed to grab the ball on the ricochet to close out the win for the Illini.

5. Miami 16, Syracuse 10: Gedney down at three-yard line

In a matchup of top-10 teams late in 1992, No. 1 Miami was outlasting Syracuse — but barely. A late comeback attempt by Marvin Graves had the Orangemen within striking distance, but ultimately three yards short of the end zone as the late Chris Gedney was tackled as time expired. Miami won, with their lone loss coming in the Sugar Bowl to Alabama. Syracuse would end up 10-2 after a Fiesta Bowl win. A victory here would’ve potentially put them in line to play for a national title.

6. The Jacket Toss Game

Just a year after one infamous charge call, Syracuse had another called against them, this time while playing Duke on the road. It’s a regular season game, so far from the stakes of most of these games. But still, the late (poor) call against C.J. Fair was enough to drive Boeheim to lose his goddamn mind, run onto the court and toss his jacket in the process.

7. Richmond (all-encompassing)

No comment.

8. Pat “Tie”

I don’t put this one as high as others might because we didn’t lose the game as a result of Pat Dye’s cowardice. Feel free to disagree with me. Also, we still have championship t-shirts from this season as a result, so it totally counts.

Moments of lesser acclaim, but still notably gut-punchy:

What else would you add to this list? Certainly there are plenty more scarring Syracuse moments for us to endure once again. And if you want to share other sports-related trauma, that’s cool too (as a Knicks and Mets fan, I made the conscious decision to spare you all that novel).