Tom Glavine
For 16 seasons, Tom Glavine was an integral part of the Braves big three starters. He was the 1995 World Series MVP and was on a clear path to the Hall of Fame. He had signed multiple extensions to keep him with the team as long as he did, but in 2002, he hit free agency.
Glavine perferred to remain with the Braves and would taken less money from the Braves. However, both the Mets and Phillies gave hearty offers of four years, while the Braves were only willing to offer three.
In a moment very similar to another Braves icon, Glavine let the one extra year dictate where he went, going to a despised rival in the New York Mets. Glavine initially openly criticized the Braves for how they handled the negotiations, before backtracking and apologizing.
Still, the damage was done, Tom Glavine was no longer a Brave and deserted the team for the Mets.
Dansby Swanson
When Dansby Swanson was acquired from the Diamondbacks before the 2016 season, the hope was that he'd become the Braves Derek Jeter. While he fell far short of those expectations, the hometown kid was still a solid shortstop and a proud member of the Braves. He even started a brand call All Things Loyal to show his love for the city.
However, going into the 2022-2023 offseason, it was clear that Swanson might be out of the Braves price range. When he inked a deal with the Chicago Cubs for seven years and $177 million, it was no surprise his hometown team wasn't willing to match a contract for a enigmatic player.
If things ended there, it would have felt like a betrayal equal to that of Fried's. Unfortunately, it did not.
Instead of simply saying that he enjoyed his time in Atlanta but was looking forward to his future with the Cubs, the Atlantan decided to take a dig at his hometown, saying, "Pro sports in Atlanta are like, well, kind of a deal."
When Swanson returned to the Braves, he looked back on his time fondly, but it still felt insulting, considering all that he accomplished with the Braves.
Freddie Freeman
There have been countless pieces written on how Freddie Freeman, who seemed like he was following along in Chipper Jones's shoes, left for the Dodgers, and there are still things we don't know, but the fact remains, number 5 left.
Whether it was a bad strategy by his agent, greediness by Freeman himself, or Anthopoulos wanting a younger first baseman, Freeman had a contract offer on the table from the All-Star Break onward. Freeman, had the chance to become the highest paid first baseman in baseball had he taken the offer and a Braves legend in the same stratosphere as Chipper Jones and Hank Aaron.
Instead, he went against the advice of Chipper Jones and demanded a sixth year.
The Braves weren't willing to meet his demands, either at the year or annual salary basis, and moved on to acquire Matt Olson before the first baseman market completely dried up. Freeman, who basically overplayed his hand, went to the Dodgers on a contract that's arguably worse than the one the Braves offered.
Freeman was devastatd for it all, like Braves fans, and ended up firing his agent over the negotiations.
To make it all hurt even worse, Freeman has absolutely been worth his contract and then some. In addition to three outstanding seasons with L.A, Freeman decided to have the playoff series of his life, leading the Dodgers to the World Series and earning himself the World Series MVP.