Not exactly the same, but Steven Stamkos checks a lot of those boxes. Granted, Stamkos was only 30 when he got his first Cup and then 31 on the second Cup. Not great defensively, average skater, little playoff success prior to the Cups. He was making about $8m at the time.
So… kinda…. ish.
So, strike one, he wasn’t 34+, as you already said. Stamkos also had multiple deeper playoff runs (2011/2015/2018) in his younger days prior to winning, including one run to the Final that he lost. All in all, Stamkos has 50 career playoff goals and 100 playoff points to Tavares’ 28 playoff goals and 53 playoff points and they’re basically the same age. The way Tavares got shutout in 6 out of 7 games against the Panthers is something I don’t think Stamkos was capable of. But perhaps at 34+ Tampa Bay let him go away for good reason. And the Leafs should do the same.
If the Toronto media and fans want to blame the “core” for being bad playoff performers, perhaps it was their mentors, Marleau, Thornton, Spezza and Tavares that showed them how to be playoff losers.