Drew Brees has been with the New Orleans Saints since 2006 and in the eight years that have passed he has seen a lot of players come and go.
But this free agency period is proving particularly tough for the 35-year old signal caller.
The Saints have been clearing out a number of veterans as they look to make salary cap room in order to re-energize the roster and ultimately find the cash to tie down Jimmy Graham.
And in doing so, Brees has had to say goodbye to some of his closest friends in the game, not least running back Darren Sproles who he played with at the Chargers as well as in New Orleans.
Sproles was traded to the Philadelphia Eagles last week and, after a far from amicable split, Brees today warned that it will be a thankless task trying to replace him:
"I think a Darren Sproles only comes around once in your lifetime, in my career and in everybody's career," Brees said.
"There may be another one 15, 20 years from now. But there's not many guys like Darren Sproles. He's a special player. He's a special person. He's a special teammate."
Lance Moore, Jabari Greer, Roman Harper, Will Smith and Jonathan Vilma have all left the franchise this off season too and just six players remain from the team that won Super Bowl XLIV.
"It's tough, because a lot of those guys I've played with for eight years," explained Brees.
"Eight years, which is rare. I'd say that's very rare in this day and age, to have that amount of time with a group of guys.
"It's going to be a new team in a lot of ways, a lot of young guys stepping up into roles that maybe they haven't been in before and it's where the new leaders emerge."
The Saints have added one major free agency import in the form of Jayrus Byrd and Brees accepts things have to evolve, especially when you have a $54 million contract to pay:
"That's the business of football. Sometimes, you love it and sometimes you hate it."