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The last two decades of the Pittsburgh Pirates and free agency

It's as amazing as you might have guessed.

Bob Levey

Here's what I did all morning: Starting here, I went through two decades of Pittsburgh Pirates transactions. Names flashed in and out of my consciousness, melting the walls of reality, granting me the abilities of the Kwisatz Haderach, forcing me to see the past, present, and future at the same time without ever knowing what was really happening.

No one should have to do that. Here's an example: Between January 2, 2004 and January 6, 2004, the Pirates signed Chris Truby, Chris Singleton, and Chris Stynes.

But I'm through the other side, and I'm stronger for it. The reason I did this is to get a list of the Top 10 free agents the Pirates have signed in the post-Barry Bonds era, which started after the 1992 season. We're talking about 20 different offseasons, with 20 different sets of free agents and 20 different sets of Winter Meetings.

I left out the minor-league free agents for sanity's sake, but it should be noted that one of the team's best moves in the last two decades was giving Garrett Jones a minor-league deal. They also signed Todd Ritchie to a minor-league deal, and they turned him into Josh Fogg and Kip Wells after a couple of decent years, which isn't bad. The Pirates should get credit for those deals. But they aren't quite what we think of when we think of free agency -- established major-league players leaving one team in search of another major-league team.

The inspiration for this article was the Pirates' two-year deal with Russell Martin, who isn't a bad player. But he also signed the largest free-agent contract in Pirates history. His $17 million guarantee beats the previous record held by Pat Meares (four years, $15 million). Clint Barmes is #3 on the list of biggest free-agent contracts.

Edit: Charlie Wilmoth from Bucs Dugout points out that Meares' contract was an extension signed after an initial one-year deal. Ha ha ha ha.

The Pirates, man.

Here's a picture of Andrew McCutchen to cleanse the palate before we start ...

He's just the best, isn't he? Now, on to the Top 10 free agents signed by the Pirates in the last 20 years:

1. Jeff Suppan, 2003

Suppan was an innings-eater, throwing more than 200 innings in four straight seasons with the Royals before joining the Pirates on a one-year deal. The innings for the Royals weren't bad, either, as he had a cumulative 4.79 ERA, good for a 104 ERA+.

Suppan started the 2003 season hot, going 10-7 with a 3.57 ERA for the Pirates before he was traded to the Red Sox. Freddy Sanchez came back in the deal, and he became a fan favorite and occasional All-Star. This was easily the best free-agent sequence for the Pirates in the last two decades.

2. Reggie Sanders, 2003

No one ever wanted poor Sanders for more than a year because of his injury history, but he was fantastic for the Pirates on a one-year deal in 2003, hitting .285/.345/.567 with 31 homers.

He can't be #1, though, because he wasn't traded at the deadline. On July 31, 2003, the Pirates were 49-57, eight games back in the N.L. Central. Sanders was healthy. You're telling me that there wasn't a single team willing to part with a semi-prospect for him? What did the Pirates gain from Sanders? They drafted 11th instead of sixth or seventh, that's what.

The good news is that the #11 pick turned out to be Neil Walker, who ended up being one of the best selections in the top half of that first round.

3. Roberto Hernandez, 2006

Hernandez was signed to a one-year deal, and he was okay before the trade deadline, which allowed the Pirates to flip him for Xavier Nady. Two years later, the Pirates were able to deal Nady for Jeff Karstens, Daniel McCutchen, Jose Tabata, and Ross Ohlendorf, all of whom provided value to the Pirates in some capacity.

4. Danny Darwin, 1996

Darwin was 40, and he signed a one-year deal with the Pirates. He was quite good for 122 innings (3.02 ERA, 146 ERA+), and he was traded at the deadline for Rich Loiselle, who was a decent closer for the Pirates for a couple of seasons.

You might have noticed that a half-season of Danny Darwin is the fourth contract on this list so far.

5. Javier Lopez, 2010

Lopez was a good situational lefty for the Red Sox from 2006 through 2008, but he had arm troubles in 2009. The Pirates snatched him up and got 38 good innings for him before they flipped him to the Giants at the deadline for a couple of quasi-prospects who didn't pan out. But it was still a good gamble and a good return, at least in theory.

6. Kenny Lofton, 2003

The Pirates made a concerted effort to grab two of the three outfielders from the 2002 Giants' pennant-winning outfield. I'll just assume that trade talks for the third outfielder stalled. Lofton was okay for the Pirates in 2002, and he was a part of the trade that sent Aramis Ramirez to the Cubs for some magic beans.

7. Matt Stairs, 2003

Stairs hit .292/.389/.561, with 20 homers in 305 at-bats for the 2003 Pirates. This was the same club with Sanders, Suppan, and Lofton. Like Sanders, Stairs hit really well. Also like Sanders, the Pirates didn't trade Stairs at the deadline. That's just bizarre. How was there not a team who wanted a left-handed masher like Stairs off the bench for the playoff run?

There had to have been one offer. It was probably straight up for Ryan Howard or something.

8. Wil Cordero, 2000

One of the top-10 prospects in baseball for two straight seasons in the early '90s, Cordero was something of a journeyman when the Pirates signed him to a one-year deal before the 2000 season. He hit .282/.336/.506 before the deadline, when the Pirates traded him for Enrique Wilson and Alex Ramirez. The good news is that Ramirez hit 378 homers and won two MVPs after the trade! The bad news is that it happened in Japan.

9. Terry Mulholland, 2001

After a lousy season with the Braves in 2000, Mulholland was okay in the bullpen for the Pirates in the first half of 2001. He was traded for Mike Fetters, who was okay for the Pirates as well.

You are reading about Terry Mulholland right now. Your day is full of surprises. The next thing you know, you'll be reading about Ed Sprague.

10. Ed Sprague, 1999

The Pirates signed Sprague to a one-year deal. He literally made the All-Star team. Literally! That's because he hit .300/.402/.545 with 16 homers in the first half. On July 31, the Pirates were 50-53, 13 games out in the N.L. Central and 11 games out of the Wild Card race. Sprague wasn't traded. Like Sanders and Stairs, there had to have been one offer. The Pirates rebuffed whatever offers might have came their way. Possibly because they weren't in the habit of trading All-Star infielders, gentlemen.

Sprague hit .197/.260/.321 after the deadline.

The 10 best Pirates free agents all fall into one of two categories: Players who did well on a one-year contract before leaving, and players who did well for a half-season before being traded away. At no point was there a franchise-changer or a long-term building block. There wasn't a guy whom the Pirates secured for several years because he fit the organizational blueprint, the plan for the next several years.

If you want an explanation for why the Pirates have gone 20 years without a winning season, look at how the organization has approached the free-agent market. There was the golden offseason of 2002, when they acquired Stairs, Suppan, Lofton, and Sanders. But other than that, it's been a brutal, depressing slog for the Pirates and free agents. For almost 20 years, the Pirates' modus operandi has been a two-pronged evaluation of free agents:

1. Hey, I've heard of that guy!

2. He doesn't want more than a year or two? Well, alright! I'm sure there isn't a reason for that!

But, you know, good luck with everything, Russell Martin.

As a postscript, I've broken the last two decades of Pirates free-agent history into four categories. If I missed anyone, please let me know. You probably don't want to scan this right after lunch. The history of the Pittsburgh Pirates and free agents, from the winter of 1992 to the present day:


Frank Bolick
Mackey Sasser
Zane Smith
Lance Parrish
Charlie Hayes
Mike Kingery
Doug Strange
Pete Schourek
Pat Meares
Luis Sojo
Mike Benjamin
Derek Bell
Ron Villone
Pokey Reese
Raul Mondesi
Jeff D'Amico
Chris Stynes
Ramon Vasquez
Chris Gomez
Joe Randa
Ryan Church
Tony Armas, Jr.
Jeromy Burnitz
Bobby Crosby
Joe Beimel
Lyle Overbay
Matt Diaz
Rod Barajas
Clint Barmes (jury's still out … but, yeah)
Erik Bedard


Dale Sveum
Kevin Elster
Chris Singleton (never played/voided)

Not bad or okay (the players who just missed the top-10 list)

Dan Plesac
Mike Williams
Brian Boehringer
Julian Tavarez
Jose Mesa
Daryle Ward
Doug Mientkiewicz
Eric Hinske
Kevin Correia

Good for a half-season (traded)

Danny Darwin
Wil Cordero
Terry Mulholland
Kenny Lofton
Jeff Suppan
Roberto Hernandez
Javier Lopez

Good for a full season (not traded)

Ed Sprague
Reggie Sanders
Matt Stairs