Owner Steve Bisciotti has had to watch many Ravens walk out his doors.
Just a couple years ago, Baltimore released tight end Todd Heap, wide receiver Derrick Mason, defensive tackle Kelly Gregg and running back Willis McGahee all on the same day.
But watching wide receiver Anquan Boldin be traded to the San Francisco 49ers was toughest.
"Todd had been with us 10 years, and I can go back and say, that was the hardest one ever, honestly," Bisciotti said of letting Boldin go.
"I'm involved in the meetings. I hear the logic. We come up with pros and cons, and come down on one side of the ledger, that this is a very tough one."
Bisciotti said it was particularly difficult considering what Boldin did in this year's playoffs. Boldin caught 22 passes for 380 yards and four touchdowns in the postseason, including six for 104 yards and a score against the 49ers in Super Bowl XLVII.
The critique of Boldin, 32, has long been that he's too slow for today's NFL. But Bisciotti pointed out that Boldin has never been considered fast and still got the job done.
"It was really, really tough because he's the guy that everybody says has gotten slow," Bisciotti said. "Well, he didn't get drafted in the first round because he ran slow at the combine 10 years ago.
"Every time Joe [Flacco] was behind, then all of the sudden, did Anquan get more separation when we were down? I don't think so. I think it's a matter of he might not create as much separation, but he's proven over and over again that he's at the top of the NFL for not needing separation to come down with almost every ball."
The Ravens owner thinks it's a good move for the 49ers to add Boldin and help third-year 49ers quarterback Colin Kaepernick.
"I expect Anquan to help Kaepernick a whole lot when it comes to having a veteran like him that you can rely on, and Kaepernick is going to benefit from his presence," Bisciotti said.
Boldin, who was in Africa doing charity work with Oxfam when the trade happened, has taken the move in stride, something that hasn't gone unnoticed by Bisciotti.
"I'm more impressed with the way that Anquan handled it," he said. "And I'm not surprised, with the gentlemen that he is, and the competitor that he is.
"There are going to be tough [departures] next year and tough ones the year after. It's the worst part of the business."