Grading Dave Littlefield's Pirate Trades

Moving farther back into the mists of time . . . .

Abandon all hope, ye who enter here . . . .

Might as well keep going with the nostalgia. There seem to have been fewer and fewer trades and less roster movement generally as you go further back in time. Bullpen usage probably plays some role in that. There are a lot of trades in this list involving late-career guys that amounted to trading one piece of toast for another. Now these guys would be DFA’d, then try to work their way back from AAA. There are also a lot of six-degrees-of-separation sort of situations in here, as one bad decision tended to lead to, or result from, another.

Littlefield became GM on July 13, 2001, and was fired on September 7, 2007.

2001

RHP Jason Schmidt and 1B/OF John Vander Wal to the Giants for OF Armando Rios and RHP Ryan Vogelsong. Schmidt went 44-47 with an exactly league-average ERA in his six years with the Pirates, hampered by Gene Lamont’s arm-fragging. He went on to become an ace with the Giants. Vander Wal was getting older, but he had three solid offensive years after the trade. Rios was terrible with the Pirates. Vogelsong was still at the prospect stage and had a bad five-year run with the Pirates, posting ERAs mostly well over 6.00. He went to Asia and had some success over four years, then returned as a finesse pitcher with the Giants for five years. The first two of those were good, while the last three weren’t. Pirate fans got to see him once more.
Grade: F

LHP Terry Mulholland to the Dodgers for LHP Adrian Burnside and RHP Mike Fetters. Mulholland lasted another six years, until 43, but was mostly very mediocre. Burnside never reached the majors. Fetters pitched mostly pretty well for the Pirates between this deadline deal and another one the next year, when he moved on.
Grade: B-

C Lee Evans and RHP Todd Ritchie to the White Sox for RHPs Josh Fogg, Kip Wells, and Sean Lowe. Ritchie came apart the next year and was about done after that. Evans never reached the majors. Fogg became the ultimate fifth starter, having two years with the Pirates as close to an average starter and two below average. Wells was a classic guy-who-can’t-harness-his-stuff. He had one good and one very good year for the Pirates. He gradually came apart over the next several years, some of it the result of arm trouble. He did hit what, for a while, was the longest HR at PNC Park. Lowe had four bad months in the Pirates’ bullpen before they traded him.
Grade: A-

RHP Jose Silva to the Reds for RHP Ben Shaffar. Silva had struggled for a long time with the Pirates but was never successful, posting a 5.44 ERA over five years. He only pitched in 12 games with Cincinnati. Shaffar never reached the majors.

2002

IF/OF Ruddy Yan and LHP Damaso Marte to the White Sox for RHP Matt Guerrier. Yan never reached the majors. Marte had three good seasons and one outstanding one in Chicago. Guerrier never pitched for the Pirates but ultimately had some good seasons elsewhere as a heavily used reliever.
Grade: F

RHP Mike Fetters to the Diamondbacks for RHP Duaner Sanchez. Fetters was done. Sanchez had a terrible time in a small number of appearances for the Pirates, but emerged later elsewhere as a good reliever for several years.

OF Chad Hermansen to the Cubs for LHPs Tim Lavery and Rick Palma, and cash. I think I’ve got this reconstructed correctly. The original deal was Hermansen for OF Darren Lewis. Lewis refused to report to the Pirates, which shows that their current status as a laughing stock has been long in the making. Lavery and Palma never reached the majors. Hermansen finished his failed career with very brief appearances for several other teams.

LHP Adrian Burnside and RHP Roberto Novoa to the Tigers for 1B Randall Simon. Burnside still never reached the majors. Novoa eventually had a couple of decent seasons in relief for the Cubs. Simon played in 152 games over two partial seasons with the Pirates and accumulated -1.7 fWAR, as well as contributing to the comical atmosphere that tended to surround the Littlefield Pirates.
Grade: D-

RHPs Jon Searles and Chris Young to the Expos for RHP Matt Herges. The Pirates supposedly grew impatient when the 6’11” Young, a well-regarded prospect, didn’t add velocity. The Expos sent him on to Texas, and he became a very good starter when healthy. Searles never reached the majors. The Pirates bizarrely released Herges in spring training three months later, even though he was an established reliever. He pitched for another seven years, usually well. This was a bad one, even without the releasing part.
Grade: F

RHP John Wasdin to the Blue Jays for OF Rich Thompson. Wasdin had a few bad years and one passable one after the trade. Thompson only got 25 PAs in the majors.

RHP Mike Williams and cash to the Phillies for LHP Frank Brooks. The league by then had learned not to chase Williams’ slider, and this was his last year. Brooks got hit hard in 11 games with the Pirates.

RHP Jeff Suppan and LHP Scott Sauerbeck to the Red Sox for IF Freddy Sanchez and cash. This was a bizarre one. The original deal was Sauerback and LHP Mike Gonzalez to Boston for RHPs Brandon Lyon and Anastacio Martinez. Right afterward, the Pirates claimed the Red Sox had withheld medical information about Lyon. A follow-on deal was arranged to send Gonzalez back to the Pirates along with Sanchez, with the two RHPs going back to Boston along with Suppan. Sauerbeck was bad for Boston for a couple of months before getting hurt. Suppan also did badly in Boston, but had a number of decent to good seasons with the Cards and Brewers later on. Sanchez made three All-Star teams and won a batting title in four seasons and two months as a regular at third and then second. His offensive value was almost all tied to his batting average—he had a 99 OPS+ with the Pirates—but he was a good defensive player. As for the guys who ultimately weren’t traded, Gonzalez went on to become an outstanding reliever for the Pirates for three years. Lyon, in fact, did miss most of 2004, but went on to become a good reliever for Arizona for a number of years. Martinez threw only 11 very bad games in the majors. The original deal was better for Boston, but the Pirates won the reworked one.
Grade: A

OF Kenny Lofton, 3B Aramis Ramirez, and, incredibly, cash to the Cubs for RHP Matt Bruback, IF Jose Hernandez, and IF Bobby Hill. You may remember this one. It occurred after the banks had a word with dilettante owner Kevin McClatchy. Ramirez was a consistent run-producer for many years with the Cubs and Brewers. Lofton could still play and had several more good years with various teams. Bruback pitched in only four minor league games for the Pirates and never reached the majors. Hernandez had a 57 OPS+ and was below replacement for the Pirates, who nevertheless reacquired him a couple of years later. (See the next entry.) The Pirates touted Hill as a hot prospect, but he really wasn’t. They were reluctant to play him after the trade. He had an 82 OPS+ in most of two seasons with them and wasn’t good defensively, either.
Grade: F-

1B Randall Simon to the Cubs for OF Ray Sadler. This was an August waiver deal, and Simon hit decently for the Cubs over the last month and a half of the season. That somehow convinced Littlefield to bring him back as a free agent that fall, because repeating mistakes is a blast. (Simon hit .194 in his last go-round with the Pirates. This sitcom writes itself.) Sadler went 2-for-8 with the Pirates,

OF Brian Giles to the Padres for OF Jason Bay, and LHPs Oliver Perez and Cory Stewart. Giles was in the process of “mysteriously” going from a 35-HR guy to a 15-HR guy, but he was still a very good hitter and got on base a lot. He had seven productive seasons in San Diego. Bay became the Pirates’ marquee player for five years, including three with 30+ HRs and 100+ RBIs. Perez had one great year for the Pirates, but fell off sharply after that due to control problems. He eventually had a couple of good seasons as a starter with the Mets and many seasons as a mostly good reliever after that. Stewart never reached the majors.
Grade: B+

2004

RHP Kris Benson and IF Jeff Keppinger to the Mets for 3B Jose Bautista, IF Ty Wigginton, and RHP Matt Peterson. Seemed like the main point of this one was to recover Bautista, whom Littlefield had stupidly let get away in Rule 5. Benson remained a frustrating but still about league-average starter for another two years and two months. Then he was out of baseball for two years before attempting an unsuccessful comeback. Keppinger didn’t make it with New York, but eventually played all or parts of nine years, often as a starter, and had a 92 OPS+. Wigginton hit badly his first two months with the Pirates, then pretty well the following year, but he was so bad defensively that he was below replacement. Bautista played 400 games for the Pirates and, despite showing some power, was below replacement—bad defense again. Hardly anything in this trade worked out for the two teams involved.
Grade: C-

OF J.J. Davis to the Nationals for OF Antonio Sucre. A notorious first-round flop, Davis went 6-for-26 with the Nationals. Sucre never reached the majors.

C Jason Kendall and cash to the Athletics for LHP Mark Redman, RHP Arthur Rhodes, and cash. (No idea why both teams sent cash.) Kendall was a weak hitter at this point, but he had a lot more defensive value than folks seemed to credit him for. He also stayed very durable. He lasted another seven years. Redman had one poor year for the Pirates and hung on only briefly after that. The Pirates immediately traded Rhodes.
Grade: D

RHP Arthur Rhodes to the Indians for OF Matt Lawton. Lawton put up a 114 OPS+ for the Pirates for four months, then was traded at the deadline. Rhodes had one very good year in relief for Cleveland, then had a string of good seasons later on.
Grade: C

RHP Juan Carlos Oviedo to the Royals for C Benito Santiago and cash. Oviedo, who was known as Leo Nunez as a Pirates prospect, was a good reliever for about five years. Santiago, age 40, played six games for the Pirates, his last six in the majors. He was another of the slapstick episodes that plagued Littlefield’s tenure.
Grade: F

2005

OF Matt Lawton to the Cubs for OF Jody Gerut. After this deadline deal, Lawton didn’t do much for the Cubs. He was near the end at that point. Gerut played only four games with the Pirates, and then I think he had some serious injury. They released him two years later, and he came back to have one very good year for the Padres. This probably would have been a good deal for the Pirates if Gerut had been able to play.

IF Bobby Hill to the Padres for RHP Clayton Hamilton. Hill never played in the majors after the trade, and Hamilton never did at all.

LHP Mark Redman to the Royals for RHPs Chad Blackwell and Jonah Bayliss. Redman was done, but hung on for another two years. Blackwell never reached the majors. Bayliss had an ERA of 7.22 in 50 games with the Pirates.

LHP Dave Williams to the Reds for 1B Sean Casey. Williams was terrible after the trade and didn’t last long. Fans fantasized about Casey putting on a power show at PNC Park, but he hit just three home runs (he was never a pull hitter), although he managed a 104 OPS+. He never could play defense, so he was replacement level. The Pirates traded him at the deadline.
Grade: C-

IF/OF Rob Mackowiak to the White Sox for LHP Damaso Marte. Mack had a solid season for Chicago, but fell off a cliff right after that. Marte pitched well out of the Pirates’ bullpen for the next two seasons and four months.
Grade: A-

2006

1B/OF Craig Wilson to the Yankees for RHP Shawn Chacon. First of a string of deadline deals. Wilson was done at that point. Chacon pitched badly as a starter the rest of that year but pretty well in 64 games, mostly in relief, the next year.
Grade: B

RHP Roberto Hernandez and LHP Oliver Perez to the Mets for OF Xavier Nady. Hernandez pitched well the last two months for New York, then was washed up. Perez had two solid seasons with the Mets, then ran into injury problems before later emerging as a reliever. Nady had a 117 OPS+ in 269 games with the Pirates.
Grade: B

1B Sean Casey to the Tigers for RHP Brian Rogers. Casey lasted another two years or so and was replacement level, but he had some value as a bench bat. Rogers had a 9.28 ERA in 13 games for the Pirates.
Grade: D

RHP Kip Wells to the Rangers for RHP Jesse Chavez. Wells made just two starts for Texas. He hung around for years after that but never had any success. Chavez pitched poorly the rest of that year and had a slightly better than average ERA in 73 games the next year. The Pirates then traded him (for Akinori Iwamura), and he lasted for many years, including a good 2024 season at age 40 and four games at age 41 in 2025. Most of that came in relief, but he even had a couple of good years as a starter.
Grade: B-

2007

LHP Mike Gonzalez and IF Brent Lillibridge to the Braves for 1B Adam LaRoche and OF Jamie Romak. Gonzalez missed some time with Atlanta, but when he pitched in his three years with them, he was very good. Lillibridge played in the majors for parts of six years but never hit. LaRoche had a 112 OPS+ and 58 home runs in 375 games with the Pirates. Romak reached the majors only briefly with other teams.
Grade: B+

OF Rajai Davis and RHP Steve MacFarland to the Giants for RHP Matt Morris. This trade seemed to be an effort by Littlefield to save his job. There were stories at the time that the money he spent on Morris kept the Pirates from signing some of their draft picks. There were also stories that other GMs were incredulous that Littlefield picked up all of Morris’ salary. Anyway, Morris was done. He had a 7.04 ERA in 16 starts with the Pirates. MacFarland never reached the majors. Davis fashioned a 14-year career as a speedy outfielder. He had only a career OPS+ of 86, but he stole 415 bases.
Grade: F (or A+ for getting Littlefield fired)