Eh, that depends on how you define "win".
If you mean sell as many units as Apple and never get bought? Sure.
But as someone who also owned an OG Pebble, if the "Pebble-way" was actually better, it would have won.
Winning might have meant getting acquired, or even just competitors making devices similar in spirit to theirs, but it'd still be a victory.
The "Apple Watch way" was the anti-thesis to the Pebble philosophy with it's needing daily charges and it's color screen, and trying to be a second phone on your wrist with beefy specs. While the Pebble was trying to be _literally_ a smarter watch.
And Apple's way won out. People just preferred that.