And yet it is important to remember that Friedman surprised many observers when he dealt 21-year-old Delmon Young to the Twins following the 2007 season after the outfielder hit .288 with 13 home runs and 93 RBIs, a performance that led to Young finishing second in the Rookie of the Year balloting behind Boston's Dustin Pedroia.
That trade turned out to be huge, as it brought shortstop Jason Bartlett and pitcher Matt Garza to Tampa Bay, two acquisitions which helped the Rays win the AL pennant.
This year, Upton, 24, had a sensational postseason (.288, 7 HR, 16 RBIs in 16 games) after batting .273 with nine homers and 67 RBIs in 145 regular-season games. He is arbitration eligible after the 2009 season.
If Friedman would deal Young, a younger player coming off a better regular season and farther away from free agency, logic follows that he could perhaps be convinced to move Upton if the right offer comes along, especially if the Rays do not lock up Upton to a long-term deal as the club already has with several of its other young stars.
Upton's upside would make him very attractive to teams needing a power-hitting center fielder. He is the kind of talent that would bring quite a haul if the Rays were to go that route.
While not commenting on any specific player, Friedman said the Rays are a franchise that must consider all options when it comes to improving the team in both the short and long term.
"I think it's important in trade talks to be willing to give up value to get value, and we've demonstrated that time and time again," he said. "It's about identifying the excesses that you may have and properly identifying your weaknesses in trying to line up with another team and if we're able to do that I anticipate we'll make a few deals this winter, and if we can't then we won't."
The Rays have depth in starting pitching, and not in the outfield, where they are looking for help in right field. The Rays, however, have shown they can get creative when it comes to addressing needs.
"We've got a lot of moving parts, we've got some depth in certain areas," Friedman said. "On the pitching side, we've got some depth but we're also sensitive to feeling too confident about that depth and opening up the season and on the fifth day of the year starting a sixth-year free agent. So we're going to approach it in such a way as we have the last couple [years] which is to focus on specific target players that we have and if we're able to acquire them then we'll be aggressive doing so and if not we're not going to be doing something just for the sake of doing something."
Friedman said he has been in conversations with several teams this week but doesn't expect anything to happen before the meetings adjourn on Thursday.
"Just a lot of preliminary conversations similar to last year, probably take a month or so to fully appreciate just how productive these meetings have been, but the conversations are just as active as they were last year," he said.