IMHO he's phrased this wrong...
Had he said "I've always WON things in my 2nd season" then factually, that's accurate, and no one can have an issue with it....
But by saying "I always WIN THINGS in my 2nd season" is kinda trying to predict the future, and also setting himself up for a massive failure!
It's akin to us "Always" winning something when the year ends in '1'....
Until we didn't...
For 3 decades running!!
1901, '21, '51, '61, '71, '81, '91 is only SEVEN times out of a possible 12... that's just over half...
Hardly ALWAYS, is it?