If you have any doubt about the Pirates being the most hopeless franchise in baseball, check out this list of major transactions made by Devil Rays GM Andrew Friedman since last October. Since then, Friedman has received the following players:
Joel Guzman - Young, high-upside hitting prospect from the Dodgers.
Dioner Navarro - 22-year-old catcher who has already played parts of three big-league seasons.
Justin Ruggiano, Sergio Pedroza - Interesting hitting prospects.
Mitch Talbot, Chuck Tiffany, Edwin Jackson - interesting pitching prospects.
Ben Zobrist - potential big-league utility infielder.
In return, the Rays gave up:
Mark Hendrickson, Danys Baez, Lance Carter - mediocre (or worse) pitchers.
Aubrey Huff, Julio Lugo - rentals.
Toby Hall - mediocre catcher.
Compare all that to Dave Littlefield's trading activity since then.
-Traded Bobby Hill for Clayton Hamilton. Neither player is going anywhere.
-Traded Dave Williams for Sean Casey and most of his contract. That didn't help.
-Traded Mark Redman for Jonah Bayliss and Chad Blackwell.
-Traded Rob Mackowiak for Damaso Marte.
-Traded Kip Wells for Jesse Chavez.
-Traded Craig Wilson for Shawn Chacon.
-Traded Roberto Hernandez and Oliver Perez for Xavier Nady.
-Traded Casey for Brian Rogers.
For all the trades the Bucs made, they got four players who might conceivably help them in a couple years. Three are relievers, and one of those (Marte) is an old reliever. The fourth is Nady, who is older and has less upside than one of the players he was traded for. In fact, the Pirates probably gave up at least as much in trades as the Rays did for all the prospects they got.
Obviously, the Rays are also drafting better than the Pirates, but a good portion of the strength of the Rays' system also comes from the talent they've acquired in trades in the past year. The Rays are a bad team, but at least they can legitimately claim they're trying to do something to improve their future. Friedman shows that a team that's really trying can improve its organizational depth a whole lot in just a year.