At the top of Melvin's list was a swap he made in June 2001 as GM of the Rangers, sending a then-18-year-old Edwin Encarnacion along with outfielder Ruben Mateo to Cincinnati for a right-hander named Rob Bell. But this is Brewers.com and Melvin spent more years in Milwaukee, so he ponders a more recent example.
His choice will not surprise those who have followed the team over the past decade: A July 28, 2006, blockbuster that brought closer Francisco Cordero and outfielders Kevin Mench and Laynce Nix to Milwaukee for free agent-to-be Carlos Lee -- and an outfield prospect named Nelson Cruz.
Today, Cruz is one of baseball's most feared power hitters, coming off consecutive seasons of 40-plus home runs. But at the time of the trade, he had just turned 26 and already had been traded twice. In his first 104 games of the 2006 season at Triple-A Nashville, Cruz was hitting .302 with 20 home runs and 73 RBIs.
"If I look back on it," Melvin said, "I maybe could have made that deal without throwing Cruz in. I look back on that one."
As with all big trades, this one has a complex backstory.
Lee, acquired in another trade from the White Sox, had a huge 2005 season for the Brewers and was on his way to even better in a contract year in 2006. Teams began calling to express interest as the non-waiver Trade Deadline approached, but Melvin and Brewers principal owner Mark Attanasio wanted to keep Lee, so together they called agent Adam Katz with a five-year contract proposal.
"I think it was $11 million a year," Melvin said. "I said to Adam Katz, 'If you could get back to me within the next 24 hours or so, I would appreciate it.'"
Less than an hour later, Katz called back.
"He said we weren't even close," Melvin said. "So I said to Mark, 'I think we should move him, and move him quick.' If word got out that we weren't even close with that kind of offer, I thought it would be harder to trade him."
Texas emerged as the strongest suitor that same day, and Melvin and rookie Rangers GM Jon Daniels quickly worked through their options. Cruz was the final piece added to the puzzle.
Melvin's willingness to include the slugging prospect was influenced by the fact the Brewers had Corey Hart ready to take over one outfield corner, and Geoff Jenkins in the other. With no designated hitter in the National League, it was difficult to see Cruz's immediate fit. Plus, the Brewers would get control of Cordero and Mench for multiple seasons.
Cordero proved a solid acquisition before he departed in free agency, but Mench and Nix did little in Milwaukee, and none of those players were around when the Brewers finally reached the postseason in 2008. Brewers fans have cried foul in the years that have followed about Melvin letting Cruz get away, ignoring that it took years in the wake of the trade for Cruz to develop into a bona fide threat. When he missed the cut for the Rangers in 2008, they designated Cruz for assignment, and he cleared waivers.
"Any team could have had him for $20,000, and they all passed," Melvin said.
Still, it's a trade Melvin sometimes ponders.
"They're all good experiences," Melvin said. "You sometimes manage by storytelling. You revisit things you've done, you talk about them. We might not have been able to make the trade if we wouldn't have put Cruz in. I don't know that."