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The original was posted on /r/hobbydrama by /u/AidanGLC on 2025-03-14 19:28:10+00:00.

Foreword: This story does not involve drama in the “controversy and/or fisticuffs” sense of the word, but it is chock full of drama in the “extremely exciting and tense series of events leads to unexpected outcome” sense of the word.

In the last half-decade, men’s road cycling has come to be dominated by a handful of riders typically referred to as “the Big Six”: Tadej Pogacar, Primoz Roglic (both Slovenia), Jonas Vingegaard (Denmark), Remco Evenepoel, Wout Van Aert (both Belgium), and Mathieu Van Der Poel (Netherlands). Since 2020, these six riders have won 11/15 Grand Tours (the big three-week stage races in Italy, France, and Spain), 17/24 Monuments (the five hardest, most prestigious one-day races each calendar year), and 5/10 World Championships (every year features two WCs – one Time Trial and one Road Race).

The post that inspired this one centered on one of the seven Monuments since 2020 that wasn’t won by one of the Big Six – Sonny Colbrelli’s victory at the biblical epic that was Paris-Roubaix 2021. Today’s post is about another of those seven, and about one of the greatest heists in the modern history of the sport.

The Sport: Pro Cycling. u/Nalc’s inflategate post summed the sport up better than I ever could, so I’m not going to reinvent the wheel here, and full credit goes to them for the description below (with a handful of minor additions from me):

It’s a professional sport, these guys make peanuts compared to many other sports (a record-breaking salary for a 3-time Tour de France winner is a cheap veteran deal for a rotational linebacker in the NFL), with about 15-20 top-level professional teams that automatically are invited to every big race, plus some lower-level teams that race on an invitational basis. It’s a team sport – every team brings 7 riders, and they are all working to get one rider the victory. There may be multiple riders that are options based on how the race plays out, but once the strategy is clear, the team is all-in for that leader. ‘Drafting’, or following closely behind another rider for aerodynamic benefit, is absolutely key to cycling. Riders will take turns being on the front, which requires the most energy. Ideally, the team leader will have teammate(s) to draft behind for as long as possible. When most of the support riders are gone, the race has ‘shattered’ or ‘blown up’. Riders will make impromptu temporary alliances in order to work together, and knowing when to make these alliances (and when to break them) is what makes racing exciting. There are different styles of rider – some are bigger (faster on the flat roads), some are smaller (faster on the hills). Some are good bike handlers (faster over rough or technical terrain), some are bad bike handlers. Some can put down a big, steady power for a long time (time trialist), some can do a huge burst of speed right at the end (sprinter). Some can put out a big effort and then recover and do it again, others cannot. The riders all have individual styles, and they know each other’s styles which informs how they work together after the race has shattered. This is not a race where the fastest person will get out to the front and stay there, since that requires the most energy and even the strongest riders will likely get caught. It’s all about timing when you want to get onto the front.

Finally, some terminology – ‘breakaway’ is a small group that is off the front, ‘peloton’ is the main group, ‘chase group’ is a group in between. “taking a pull” means riding at the front of your group (doing the most work, to the benefit of the riders behind you), “attacking” is when you make a strong effort to go faster than your current group (due to the drafting benefit, you need a lot of strength or perfect timing to quickly get far enough ahead that the other riders cannot draft you), you’re “dropped” if you’re no longer able to keep up with the group you’re in, and “sprinting” is the high speed acceleration at the very end of a race.

The Race: 2022 Milan – San Remo. MSR is the first of cycling’s five Monuments in the calendar year, taking place in mid-late March, and has been raced every year since 1907 save for 1944 and 1945. It’s also the longest, around 300km running from Milan to the seaside town on the Franco-Italian border. Terrain-wise, MSR is the simplest of the Monuments – it lacks the cobblestone roads of the Tour of Flanders or Paris-Roubaix, or the brutal climbs of Liege-Bastogne-Liege or Il Lombardia. It’s relatively flat, with only around 2,000m of total elevation gain over the whole race (by comparison, Il Lombardia, the other Italian Monument, has nearly 5,000m of climbing). There is one major climb at the middle of the course (at which point the race has not yet broken apart) and then two relatively short climbs near the finish: the Cipressa (which tops out 22km from the finish) and the Poggio di San Remo (which tops out 4.5km from the finish). Both climbs are significant enough that a hard-charging team can shake loose weaker riders, but neither is long enough or steep enough to allow an attack to stick through sheer brute force. If you attack on the Poggio, timing and racecraft matter as much as power. Once riders hit the top of the Poggio, they must navigate an incredibly technical descent – hairpin turns and tight corners the whole way down – before a flat run-in to the finish line.

MSR is often referred to as the easiest Monument to finish and the hardest Monument to win. This is because there are many ways to win it: it can be won from a bunch sprint at the finish (Jasper Philipsen in 2024, Julian Alaphilippe in 2019), or from a sprint between a few riders who have gone clear earlier in the race (Jasper Stuyven in 2021, Wout Van Aert in 2020). It can be won from an attack on the Poggio, either on the ascent (Mathieu Van der Poel in 2023, Vicenzo Nibali in 2018) or on the descent. It can theoretically be won by an attack on the Cipressa, as attempted (unsuccessfully) by Nibali in 2014. It can also be won by a wide variety of riders: the names in the previous sentences include pure sprinters, classics riders, Grand Tour winners, and breakaway specialists. This makes planning for the endgame incredibly difficult: to take another Monument, there is a reliable way to win Liege-Bastogne-Liege and only a handful of riders each year who can realistically do so; there are four or five different ways to win MSR, and thus a far larger pool of riders who can potentially win it. This also means that the finish of MSR always features a lot of fireworks. Lots of people can win it, so lots of people try to win it. The first ~285km of Milan-San Remo are generally dull; the finale is the best 10km in the sport.

Dramatis Personae (and their teams)

Tadej Pogacar (UAE Team Emirates): Pogacar is an all-rounder and widely regarded as one of the 2-3 greatest men’s cyclists of all time. Equally comfortable in Grand Tours and one-day races, on the eve of 2022 Milan – San Remo he is the reigning winner of the Tour de France (in both 2020 and 2021), two Monuments (Liege and Lombardia), Strade Bianche (a brutally hard race on gravel roads in Tuscany that is sometimes considered an unofficial Sixth Monument), and Tirreno-Adriatico – a one-week stage race that immediately precedes MSR. 2022 is his second appearance at MSR, having finished 12th in 2020, and he is among the favourites.

Wout Van Aert and Primoz Roglic (both Jumbo Visma): a cyclocross racer who transitioned to road-racing in 2019, Van Aert is the most versatile cyclist of his generation. In 2020, he won both MSR and Strade Bianche, and came third in the 2021 edition of MSR. In the 2021 Tour de France, he became the first rider since 1979 to win a mountain stage, a sprint stage, and a time trial stage in the same Tour.  Coming into this race, he is the reigning winner of Omloop Het Nieuwsblad (the opening race of the WorldTour classics season) and the points classification of Paris-Nice – another one-week stage race immediately before San Remo. He is accompanied by Primoz Roglic, the reigning Vuelta a Espana and Olympic Time Trial winner and fresh off the overall win at Paris-Nice. Roglic is not generally expected to win MSR, but his presence is seen to be returning a favour – Van Aert was instrumental to Roglic’s Paris-Nice win, and he will now support Van Aert’s attempt to win a second Milan-San Remo.

Pogacar and Van Aert are by far the favourites for this edition of MSR. It’s widely anticipated to end in a dual between them, either as a two-up sprint at the finish line or a contest to see who can go clear on the Poggio. However, there are a few other riders worth mentioning:

Mathieu Van Der Poel (Alpecin-Fenix): Another cyclocross racer who has transitioned to road-racing, and one of the greatest classics riders of all time. He’s from a family of cycling royalty – his father was a six-time Dutch National Champion, and his grandfather won MSR in 1961. He and Van Aert have also been rivals since childhood, having together won seven of the last eight cyclocross world championships (with the other nearly always in 2nd). At this point, MVDP is the winner of the 2020 Tour of Flanders (be…

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