The first time it happened, way back in 2008, he was heartbroken. On that day in Interlagos he stood atop the rostrum, hand over his heart, holding back tears of disappointment.
For 30 seconds he had been champion, only to have the crown snatched from his grasp by Hamilton's final-corner pass on Timo Glock. Massa had driven the best season of his life and missed out by a single point; second place was no consolation.
But as he received his trophy at Abu Dhabi on Sunday, the smile was genuine. Though it had been for a single race win, not the title, he had again pushed Hamilton close.
Twelve months ago, even he wouldn't have seen that coming.
Massa had just been ejected from his Ferrari seat after four dismal, disappointing seasons alongside Fernando Alonso. The highs of 2008 were long forgotten as the Spaniard stamped his authority over the team, leaving Massa further and further behind as the years rolled by.
In 2010, the gap between the pair at the end of the season was 108 points. Alonso fought for the title in the final race; Massa barely held on to sixth.
The gap grew to 139 points in 2011 and 156 points in 2012, before shrinking slightly to "just" 130 points in 2013. It's difficult to recall any driver being so comprehensively outclassed by a team-mate for such a long period of time.
After three years of rumours his seat was under threat and many fans calling for him to go—and even exit F1 entirely—it finally happened. Kimi Raikkonen was announced as a Ferrari driver for 2014, and Massa was in limbo.
Some, including Martin Brundle and Ted Kravitz of Sky Sports, thought he could be leaving the sport.
Though no one would admit it, the decision was as much to do with the sponsors Massa could attract as it was with what he could bring as a driver. He'd be paired with rising star Valtteri Bottas.
The duel between experience and unrefined talent went the way of the Finn through the opening part of the season. Massa had proved he would not be pushed around by defying team orders in Malaysia, but his inability to get results on the board was worrying.
Bottas reeled off five consecutive points finishes in the first five races for a total of 34, while Massa's two seventh-placed finishes had netted him only 12.
The Finn's first (and as it turned out, only) retirement of the season, from eighth place in Monaco, allowed Massa to close the gap slightly.
But in Canada, the gulf widened once more in spectacular fashion.
F1Fanatic's lap charts show that had he shown a little more cutting edge when attacking, he could have had a chance of victory. Instead, he was taken out in a clumsy, high-speed tangle with Sergio Perez on the final lap, missing out on a potential podium finish.
Massa responded by qualifying on pole for the next race, but fell back to fourth as Bottas' superior race pace saw him claim the team's first podium of the year. Further podiums for the younger man followed in Britain and Germany; Massa retired from both races on the opening lap.
With 10 of the 19 races gone, Bottas had three podiums, nine top-10 finishes, 91 points and was fifth in the championship standings. His one retirement was due to a mechanical failure.
Massa had no podiums, four top-10 finishes and just 30 points. He was 10th and had retired four times—every time due to a collision. His car was a magnet for trouble and he was being outperformed by a man now being tipped as a future champion.
But just as he was being written off for the fifth season in a row, Massa found his form and made it to the chequered flag in every one of the final nine races of the year.
At Spa he lost time after picking up debris in his front wing and finished 13th, while in Russia he was hampered by a power loss in qualifying. Starting 18th, he took a wrong turn on strategy and could only manage 11th.
In the other seven, he scored points—lots of points.
More points, in fact, than Bottas.
The veteran scored more than three times as many in the second half of the season than he did in the first, adding 104 to his total and scoring three excellent podiums—each one ahead of Bottas—along the way.
The Finn, with three additional podiums of his own, chalked up 95 points. His final championship position was fourth, with 186 points. Massa ended in seventh, 52 behind, having completed a remarkable turnaround.
Massa's race to second in Abu Dhabi was the icing on what should be considered a successful season.
Long regarded as a "confidence driver" whose head drops when things aren't going his way, the 33-year-old overcame a dreadful first half of the year to record his best string of results since that brilliant, painful 2008 season.
Better still, Ferrari replacement Raikkonen spent 2014 proving Massa hadn't done that badly against Alonso after all.
Massa can fly off home to Monaco or on holiday to Brazil this winter, able to reflect on a job well done.
And I, as one of those who thought he should go at the end of last season, shall enjoy my humble pie.