Steven Gerrard never regretted his decision to stay at Liverpool. He said that even if he had won the title at Chelsea, it would not have meant as much to him as what he achieved with his club. He got the lot, bar that.
For Matt Le Tissier, bragging rights were enough. He saw it like this. When he had retired and all the old pros went to the bar, there would be a few who could say they had more medals than him, but none who could say they were better at football.