Gehrig’s line was “Today I consider myself the luckiest man on the face of the earth,” and it was delivered the day he played his last game for the Yankees.
Given that a show set in Boston would probably never use a quote from a Yankee to end things with, I’m pretty sure Sam’s line (which wasn’t worded the same anyway), was meant in a good way. He really did think he was the luckiest SOB on earth.