The Dutchman was well-placed and on the attack with Przemyslaw Niemiec (Lampre - Merida) Tanel Kangert (Astana Pro Team) and eventual winner Benat Intxausti (Movistar Team) as Stage 16 was drawing to a close when on the cobbles of Ivrea, Gesink suddenly was forced to stop on the side of the road. There were two kilometres remaining.
"I've never experienced anything like this before," Gesink explained after the race. "To have this happen after 236 kilometres, just two short of the end - it must be Muphy's law. My chain derailed on the cobble and blocked my wheel. I was riding full out for the stage win and felt very good.
"Anything could have happened, but going out in this manner is a big disappointment even though it did show I am back in form."
Gesink eventually crossed the finish line in 17th place, 23 seconds in arrears of Intxausti. He moved from 13th to twelfth on the general classification, 7:47 behind maglia rosa Vincenzo Nibali.
Gesink's young teammate, Wilco Kelderman featured in the day's break and put in a strong showing as the peloton began to reel in the escapees, launching multiple attacks.
"On that last climb, the tempo was just too much for me," Kelderman said. "I was passed by the group of favourites with Robert in the mix and then went on at my own pace. In the end, I finished twenty-fifth in a group together with Domenico Pozzovivo. I want to give a go again yet this week but tomorrow is going to be tough. My legs are going to be tired after today."
He remains third in the classification for best young rider behind Carlos Betancur (Ag2R La Mondiale) and Saxo - Tinkoff's Rafal Majka.