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Who's the unluckiest rider in pro cycling?

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Andreas Klöden was the original Landa.
Worked for and against Ullrich, Vino, Contador, Levi, and Armstrong like Landa with Aru, Froome, Quintana, and Valverde, while potentially having to to with Caruso, Haig, and Mäder.
Sick and crashes from 2001-2003 meaning he can’t capitalize on his 2000 form.
Close to winning in 2004 and 2005 Tour stages.
Injury in 2005 Tour.
2006 with less teammates and someone said he crashed before the race but I don’t remember. Had the high potential to win that year.
2007 crash and injury again plus Vino causing team to be withdrawn when he was sitting in a good position to finish top 5 and maybe podium ahead of Levi with how it ended.
2008 could have top 5 the Giro before he got sick and lost his placing when 6th.
2009 getting 6th while having to work for Armstrong when he was stronger.
2011 crashing out when he had a good chance to top 5 in the form he was showing.
2012 being hampered by the 2011 crash as he never really recovered climbing wise.

I have mixed feelings. Looking at his career results, he probably over achieved in one week races (5 major victories, not many placings, nor huge amount of top 10's), and under achieved in grand tours (too TDF focused); though it could have been far worse. Imagine if he'd have to wait for Ullrich in 2004, and if he'd had to support Jan in 2006....maybe Andreas would have finished bottom half of the top 10 and nobody would have ever known that he had podium potential.

Also, time trials were more prominent during his career, which was lucky, in a way.

Yes, in March 2006 he did his collarbone from memory, which meant that he was a little underdone entering the Tour. Probably could have won that as you said (might not have been dropped in the Pyrenees).

2007 was arguably his best season and form though. Without that early crash and eventual team withdrawal, who knows? Would have been nice to see him battling it out with Contador, Evans and Levi.

2008 outside chance to podium Giro or Vuelta without misfortune.

2009 he was also helped a little by TTT.

For Klöden, cycling was a job first, sport second. Not sure if all of 2001-03 and 05 was due to bad luck. Also, maybe he didn't feel like it was worth all the 'risk' some seasons (like 2010, after allegations), but that's conjecture, and can argue for or against being a great talent.
 
I have mixed feelings. Looking at his career results, he probably over achieved in one week races (5 major victories, not many placings, nor huge amount of top 10's), and under achieved in grand tours (too TDF focused); though it could have been far worse. Imagine if he'd have to wait for Ullrich in 2004, and if he'd had to support Jan in 2006....maybe Andreas would have finished bottom half of the top 10 and nobody would have ever known that he had podium potential.

Also, time trials were more prominent during his career, which was lucky, in a way.

Yes, in March 2006 he did his collarbone from memory, which meant that he was a little underdone entering the Tour. Probably could have won that as you said (might not have been dropped in the Pyrenees).

2007 was arguably his best season and form though. Without that early crash and eventual team withdrawal, who knows? Would have been nice to see him battling it out with Contador, Evans and Levi.

2008 outside chance to podium Giro or Vuelta without misfortune.

2009 he was also helped a little by TTT.

For Klöden, cycling was a job first, sport second. Not sure if all of 2001-03 and 05 was due to bad luck. Also, maybe he didn't feel like it was worth all the 'risk' some seasons (like 2010, after allegations), but that's conjecture, and can argue for or against being a great talent.
If anything I feel like he underachieved in Grand Tours and stage races. He had 8 top 10 placings in the big ones with the 5 wins and 2 small stage race wins. Without all the injuries maybe he wins some of the smaller ones instead of second.

2009 he also had to help Armstrong. Without him maybe he makes up the 41 seconds to third or isn’t dropped like a log on stage 17.

Maybe not but he always seemed to be injured and that doesn’t help. The costs of being skinny riding a bike.
 
Because he is unlucky!

This year I'm voting for Alaphilippe.

As usual, though, I think that outside of an Opi-Omi, many crashes can be avoided or mitigated by positioning and awareness. Not all, of course.
And that positioning and awareness is a skill, which Thomas has little of. Similarly, I could vote for Igor Antón, but most of his misfortune was due to his own lack of skill regarding descending, positioning etc.. For somebody who came from the track and for most of his career was a classics man, Thomas has a surprising lack of bike handling skills. As a result he'd failed to accumulate a palmarès in the races that count in the Classics commensurate to the strength he'd shown in races before that, had reinvented himself as a stage racer (which could be considered very fortunate that he had that string to his bow, but discussion of it will be difficult in this part of the forum) but had crashed out of more or less every stage race he'd been given the chance to even co-lead, then was handed the chance to lead due to a fortunate set of circumstances surrounding Froome's salbutamol positive (like Evans in 2011, there's a good chance he doesn't win without that as Froome most likely does not ride the Giro and targets winning a 5th Tour to tie the record).

I just feel like, a lot of Thomas 'bad luck' is his own fault due to issues with placement and bike handling (the bidon crash in the 2020 Giro is an example of genuine misfortune, though, I feel), and the amount of things that had to fall into place for him to be in position to win the Tour are an example of extreme good fortune in cycling, not bad fortune, and benefiting from all of that rather counters the interpretation of him as an 'unlucky' cyclist.
 
And that positioning and awareness is a skill, which Thomas has little of. Similarly, I could vote for Igor Antón, but most of his misfortune was due to his own lack of skill regarding descending, positioning etc.. For somebody who came from the track and for most of his career was a classics man, Thomas has a surprising lack of bike handling skills. As a result he'd failed to accumulate a palmarès in the races that count in the Classics commensurate to the strength he'd shown in races before that, had reinvented himself as a stage racer (which could be considered very fortunate that he had that string to his bow, but discussion of it will be difficult in this part of the forum) but had crashed out of more or less every stage race he'd been given the chance to even co-lead, then was handed the chance to lead due to a fortunate set of circumstances surrounding Froome's salbutamol positive (like Evans in 2011, there's a good chance he doesn't win without that as Froome most likely does not ride the Giro and targets winning a 5th Tour to tie the record).

I just feel like, a lot of Thomas 'bad luck' is his own fault due to issues with placement and bike handling (the bidon crash in the 2020 Giro is an example of genuine misfortune, though, I feel), and the amount of things that had to fall into place for him to be in position to win the Tour are an example of extreme good fortune in cycling, not bad fortune, and benefiting from all of that rather counters the interpretation of him as an 'unlucky' cyclist.
I feel like the crash he had in the Tour wasn’t primarily his fault has he got shoulder checked by someone taking a terrible line at too high a speed. With the crashes he reminds me of Menchov.
 
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And that positioning and awareness is a skill, which Thomas has little of. Similarly, I could vote for Igor Antón, but most of his misfortune was due to his own lack of skill regarding descending, positioning etc.. For somebody who came from the track and for most of his career was a classics man, Thomas has a surprising lack of bike handling skills. As a result he'd failed to accumulate a palmarès in the races that count in the Classics commensurate to the strength he'd shown in races before that, had reinvented himself as a stage racer (which could be considered very fortunate that he had that string to his bow, but discussion of it will be difficult in this part of the forum) but had crashed out of more or less every stage race he'd been given the chance to even co-lead, then was handed the chance to lead due to a fortunate set of circumstances surrounding Froome's salbutamol positive (like Evans in 2011, there's a good chance he doesn't win without that as Froome most likely does not ride the Giro and targets winning a 5th Tour to tie the record).

I just feel like, a lot of Thomas 'bad luck' is his own fault due to issues with placement and bike handling (the bidon crash in the 2020 Giro is an example of genuine misfortune, though, I feel), and the amount of things that had to fall into place for him to be in position to win the Tour are an example of extreme good fortune in cycling, not bad fortune, and benefiting from all of that rather counters the interpretation of him as an 'unlucky' cyclist.

Absolutely, agree on all points here. Placement is really key. That was probably the main reason why LA finished first in 7 TdFs. (well, the main cycling reason...). He and USPS were always near the front of the peloton. When Thomas hit that bidon in the Giro -- in which he was one of the favorites -- he was at least midpack. Even in a throwaway stage, that's no bueno.
 
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Absolutely, agree on all points here. Placement is really key. That was probably the main reason why LA finished first in 7 TdFs. (well, the main cycling reason...). He and USPS were always near the front of the peloton. When Thomas hit that bidon in the Giro -- in which he was one of the favorites -- he was at least midpack. Even in a throwaway stage, that's no bueno.

Thomas hit the bidon in the neutral zone.
 
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We could argue about luck or skills.

Menchov was extremely unlucky but then again, he was the culprit of his own bad luck in some cases. I'm still pissed he threw away TdF '08 by poor positioning (40" split in stage 3) and his bad downhill skills (35" split in Jausiers). Just without those time losses he would have been 2nd.

Add to the mix his impossible uphill crash when he was going alone in Prato Nevoso and there you have it kids, that's how you stupidly lose a TdF.

Johnny Hoogerland was another unlucky rider. Porte, Thomas, Vanmarcke are both unlucky and unskilled.
 
Craddock fracturing a bone in his hand after tripping over TV cables at E3 springs to mind.

Also Geniets being hit by an advertisement board at P-N.

Matthew White breaking his collarbone on the day of the Grand Départ in Liege 2004.

Which meant Cofidis would either have to start a rider down or have to scramble for someone somewhere.
So, literally 3 hours before the start, Peter Farazijn got a phone call telling him to hurry over there.
I say Peter, his wife got the call but Peter had taken their son (ex-pro Maxime Farazijn) out for the day, they biked over to Ypres to watch the Car-rally.
So his wife called him on his cell (he only bought it a month ago) and he hurried towards his home, got in the car with his wife who sped all the way over the highways to Liege where Peter arrived in plain clothes 30 minutes before he was due to start. (There is a legendary interview with Sporza which I can't find anymore).
He would start (without any proper preparation) and eventually finish it.

So, I guess Matthew White was quite unlucky. But his misfortune resulted in Farazijn unexpectdly starting his 8th TDF.