The following two things can be true at once: Kyle Larson was a deserving 2025 NASCAR Cup Series champion, and Denny Hamlin was denied his first career title in a fashion so cruel and heartbreaking that it bordered on tragic.

All day Sunday, everything seemed set up for Hamlin to finally win that elusive championship: Even when he (like many others) cut a tire mid-race, it came at the best possible time after an unrelated caution, allowing him to avoid losing too much track position by ducking into the pits to fix the problem under yellow. After passing championship rivals William Byron and Chase Briscoe later on, Hamlin led the last 28 laps of regulation and had a 3.1-second lead with just three laps left …

… Until Byron blew a tire that forced the race into OT. Gambling to take two fresh tires while Hamlin took four, Larson started ahead on the restart and Hamlin was unable to overtake him before the race ended with Larson in championship position. What had seemed like Denny’s year all season long was erased in its final moments — in large part because of an incident he had nothing to do with, taking place 500 feet behind him on the track.

In short, it was a brutal way to lose the title. But just how brutal? Taking a page from Bill Simmons’ old “Levels of Losing” concept, I gathered a list of popular candidates for the most heartbreaking losses in sports history and checked which of the following categories they fit under:

• Missed Upset (1 point): When the underdog comes agonizingly close to pulling off a big upset …  only to fall just short.
• Humiliation (2 points): When the loss itself becomes a punchline — whether because of a butt-kicking rout or a meme that lives forever.
• Legacy Loss (2 points): When the defeat alters how a player, team or era is remembered.
• Self-Inflicted (3 points): When the losing side beats itself through a mistake, meltdown, bad decision, etc.
• Cursed (3 points): When fate, history and/or bad luck seem to conspire against you again and again.
• Robbed (4 points): When a bad call, a weird rule, an unlucky bounce or some other outside factor snatches victory away.
• Shock Upset (4 points): When the heavy favorite falls to an opponent no one gives a chance.
• Unraveling (5 points): When a team’s chances slowly slip away in a long, painful collapse rather than a single mistake.
• Gut Punch (5 points): When the loss lands in one cruel instant, i.e., a walk-off, buzzer-beater or last-second heartbreak.

For each painful defeat on our list, we’ll assign either full, half or no credit in each category, and then add up the points. Oh, and there’s one more twist: Championship-deciding heartbreaks get 100% of their value, while those in earlier games or rounds get a smaller fraction as their multiplier. (So a non-deciding Finals game would get 95% weight, a potential semifinal clincher would get 90%, a non-clincher in that round 85% and so forth, until we award 60% for late-schedule regular-season games and 50% for the rest of the regular season.)

Let’s start by counting down the back end of the top 25 (with ties) on the list, before we dive into the top 10:

Note that the Toronto Blue Jays’ 2025 World Series loss cracks the list as well, taking place one day before Hamlin’s played out this past weekend. That was not only a missed upset — the Dodgers were heavy favorites before the series — but it also received half-credit for legacy and curses (Toronto is perpetually a good-not-great team that finds ways to fall short) and a robbery (the ball wedged in the OF fence), plus full marks for the gut-punch of losing Game 7 after allowing the tying HR when two outs from a title. It checks in tied with other crushing championship losses like Cleveland in the 2016 World Series, Seattle in Super Bowl XLIX and Michigan’s “Fab Five” losing the 1993 NCAA title game on Chris Webber’s nonexistent timeout.

The rest of the list is stacked with familiar gut-punches and slow-motion collapses across every sport, the moments that haunt fans and athletes for decades: There’s the 2004 Yankees, the only MLB team ever to blow a 3-0 series lead, and their 2003 ALCS victory that preceded it. There are multiple Buffalo-based fiascos on hand, the 18-1 Patriots losing their perfect season via Helmet Catch, and the 2011 Texas Rangers being one strike away (twice!) from a championship before losing to David Freese and the Cardinals. There are perennial punchlines like the Browns and Mets, and the most prolific 3-point team in NBA history losing when they missed 27 consecutive 3-pointers.

Even individual agony makes the cut, from Lewis Hamilton’s controversial lost eighth world title in 2021 to Carl Edwards’ 2016 heartbreak, when a late yellow flag and restart crash with Joey Logano cost him a shot at the title in Homestead.

It’s fitting that Edwards is just outside of the tier in which Denny resides on this list, as the two incidents were eerily similar — both involving a frequent championship bridesmaid with a clear track to their first Cup crown in front of them, spoiled by a caution behind them that bunched the field back up and forced them into a chaotic restart. While Byron is just a bit more accomplished than Dylan Lupton (just a bit!), the two will go down in the history books of drivers who had tires go down that inadvertently kept NASCAR icons from joining the ranks of champions. The pain for Edwards after that incident was so great, he admitted later, that it shook his faith in racing and helped push him to step away from the sport.

But now, let’s get to the true murderer’s row of sports heartbreak — collapses and cruel twists of fate that all live in the same emotional neighborhood as Hamlin’s 2025 season finale:

We can group them further based on how each heartache happened. There’s the pure-gut-punch fellowship of missed field goals, with the 1990 Buffalo Bills (Scott Norwood) and 1998 Minnesota Vikings (Gary Anderson) seeing their promising seasons end on a pair of tragic miscues. There are the slow-motion meltdowns that build to full-scale disasters — the 2003 Chicago Cubs in the Bartman Incident NLCS and a pair of great (if almost equally cursed) golfers, Phil Mickelson at the 2006 U.S. Open and Greg Norman at the 1996 Masters. There are also the self-inflicted losses from the distance of seemingly safe leads — the 73-win 2016 Golden State Warriors blowing a 3-1 lead in the NBA Finals, and Jean van de Velde’s final-hole triple-bogey to squander a 3-shot advantage at the 1999 Open Championship.

Then there are near-misses that ruin what were supposed to be storybook seasons. The 2009 Minnesota Vikings fit this category, with a rejuvenated Brett Favre leading the way — until a back-breaking interception cost them a shot at a potential winning field goal — and so does Denny Hamlin in 2025. In a legacy-defining moment with history on the line, Denny’s championship drive proved to be Doom Dressed Up as Hope again, every bit as much as the Vikings always are. Minnesota’s loss was more of the self-inflicted variety (the No. 11 team’s crime was guessing wrong on tires in an impossible situation) while Denny fit the “robbed” category more (overtime rules are always controversial by nature), but the crushing result was the same in both cases.

Just about the only losing archetype that can produce defeats that hurt more than what Hamlin just went through are your classic curses and mega-collapses, with added gut-punches as well: the 1951 Brooklyn Dodgers (whose second-half slide was finished off by the Shot Heard ‘Round the World) and, especially, the 1986 Boston Red Sox and 2016 Atlanta Falcons. According to our scoring system, the Falcons’ much-memed blown 28-3 lead against the Patriots in Super Bowl LI was the most heartbreaking loss in sports history, and Bill Buckner and the 1986 Sox’s World Series collapse against the Mets was No. 3, sandwiched around the ‘03 Cubs.

Of note, Hamlin’s was the only loss in the group that wasn’t a “humiliation” — his defeat wasn’t a choke, nor was it embarrassing or meme-worthy. As he said in his post-race presser, he and the No. 11 team did everything they could to win at Phoenix. Similarly, his loss was the least self-inflicted out of the most painful losses — yes, he could have taken a different tire strategy and perhaps made different decisions on the restart as Larson rocketed past him on the high line. He didn’t suffer a terrible upset, coming out of an exceptionally well-balanced Championship 4 this year. Mainly, Denny’s defeat was defined by the curse of never having wins come easy at this phase of the season, and the way a late yellow flag can rob anyone of their lead as they cruise toward the finish line.

That doesn’t make Sunday’s outcome any harder to swallow. “In this moment I never want to race a car ever again,” he half-joked in the wake of the race — and in that sense, he’s just like all of the other players and teams on our list above. Often, though, what defines a great athlete isn’t what happens when they win, but rather how they pick themselves up and fight again after they lose. And we’ve seen Denny do that enough times over the years to know his greatness doesn’t depend on a championship.