I actually don't mind that particular one too much... although Jay does have a good lead which he should have won the first trick and gone with.
Since you bid in 6s and led low, a very valid assumption is that you have the 64. If I'm your partner, and I have 65 63 62 60, I might assume that you have three, but I will rely on you having at least two.
Knowing you have the 64, that makes 65 63 62 all equal on the first trick with the 60 just lowly. By playing 61 and Philip not playing a trump, I now know where six of the seven trumps are... and the missing one is the 66. If Fry has a trump, it beats mine, so why waste a high one?
I can argue both ways for taking this first trick... While the 33 looks good, that 53 does not... unless a low 3 happens to lead. Jay also knows he has the most trumps on the table in a hand he did not win the bid, so staying out of the lead for a bit is a good thing... He can either leave it with you, or let Fry take it and play last.