10 worst free agent signings in Pittsburgh Pirates history

It's been nearly a decade since the Pittsburgh Pirates last handed out a multi-year contract to a free agent.

That player, pitcher Ivan Nova, actually had a decent run with the Pirates, pitching two seasons on his three-year, $26 million deal before getting traded to the Chicago White Sox in what amounted to a salary dump.

Like Nova, the team's largest free-agent expenditure, pitcher Francisco Liriano (three-year, $39 million deal), won't make an appearance on this list. Sure, their contracts stand as the largest out-of-house signings in team history — though, technically, both Nova and Liriano were re-signed after being allowed to test free agency — but they weren't total net-negatives for the team.

Despite their long history of frugality, the Pirates have made a number of free agent blunders in their history. The size of the deals on this list aren't mind-numbing (when are they ever when it comes to Pirates contracts?), but the production from these players during their tenures in Pittsburgh ranged from "abhorrent" to "I'm literally quitting on the team".

Below, we'll rank the ten worst free agent signings in the team's long history. Money matters here, and will serve as a tiebreaker where relevant, but given how small most free-agent contracts have been for the Pirates, it isn't the only factor in these rankings. Think of this exercise as an homage to the franchise's reluctance to spend big money on good players. Sometimes, you get what you pay for.

And, spoiler alert, "Operation Shutdown" will make an appearance. You have been warned.

10 biggest free agent mistakes in Pittsburgh Pirates franchise history

10. Scott Olsen - One year, $500,000

This is a doozy to kick off the list with, as Olsen never actually suited up for the Pirates.

He actually signed an incentive-laden, $4 million deal that was only partially guaranteed and came with another $4 million club option for the following season.

In the 2010 season, Olsen pitched to a 5.56 ERA, 14.8% strikeout rate, 7.6% walk rate, and 46.5% groundball rate in 81 innings for the Nationals. He was set to join a rotation that included (avert your eyes) Kevin Correia, Ross Ohlendorf and James McDonald.

Instead, lingering shoulder problems stemming back to a labrum surgery in July 2009 prevented Olsen from ever suiting up in Pittsburgh. It was hardly a costly mistake, but the signing never made much sense from the jump.

9. Matt Diaz - Two years, $4.5 million

Here's a rare treat on this list: a multi-year deal. Don't expect too many more of those, but at least this one wasn't truly terrible.

Again, the money here is minimal (a running theme on this list), but Diaz was hardly a valuable contributor in Pittsburgh. In 100 games in 2011, he slashed .259/.303/.324, providing the team -0.5 bWAR. At least he hit .315 against southpaws, right?

Diaz was signed to be the primary left fielder, though all he gave the Pirates was -2 Defensive Runs saved combined across both corner outfield spots.

Ultimately, the Pirates traded him back to Atlanta (where he played for five seasons prior to playing with Pittsburgh) halfway through the first year of his deal, eating the remainder of his 2011 salary to pick up a player to be named later (Elicier Cardenas).

8. Lyle Overbay - One year, $5 million

Holy moly, did the Pirates have a bad offseason following the 2010 campaign (when they went 57-105) or what?

The third consecutive entrant from that free agent class on this list, Overbay was signed to be the team's starting first baseman during the 2011 season. A proven commodity after years of slugging for the Toronto Blue Jays, he was expected to hold down the fort until top prospect Pedro Alvarez was ready.

Unfortunately, Overbay turned 34 over the offseason and his production fell off a cliff. Earning the nickname "Lyle Overpaid", the veteran slashed .227/.300/.349 in 103 games in Pittsburgh, good for an 83 wRC+ and -0.6 bWAR.

Like the previous members of this list, Overbay wouldn't make it through a full season in Pittsburgh, getting released shortly after the trade deadline in early August.

7. Jeromy Burnitz - One year, $6.7 million

Talk about the big bucks. Burnitz, after reviving his career in Colorado in his mid-30s (gee, wonder why this didn't work out) signed a two-year, $12 million deal with the Pirates that included a guaranteed $6.7 million ($6 million salary in 2006, plus a $700k buyout on his option year).

The Cubs were the first ones to take a chance on Burnitz after his .916 OPS season with the Rockies, and they were rewarded with a .757 OPS and 0.3 bWAR in 2005. Nothing to write home about, but solid production that warranted a continuation of his career.

Then, in Pittsburgh, he hit six home runs in his first 19 games! Only then did the wheels fell off, and he finished the campaign hitting .230 and accruing -0.7 bWAR. He lost playing time to José Bautista at the end of the season and was booed for failing to play hard, explaining the dismal state of the team by calling himself "Joe High-Paid Free Agent."

At least he wasn't signed in 2010, right?

6. Pat Meares - One year, $1.5 million

Meares' scant salary here is technically the only one under consideration, but his journey with the Pirates goes far beyond the initial contract.

Following a successful six-year career with the Minnesota Twins, a 30-year-old Meares signed his one-year deal with the Pirates, hitting .308 in his first season in Pennsylvania. Unfortunately, that production came in just 21 games, as Meares pinched cartilage in his wrist.

Nevertheless, then-general manager Cam Bonifay gave Meares the four-year deal he was looking for, worth a total of $15 million. He would make it less than two seasons and just 219 games into that contract as he dealt with the aftermath of his wrist injury.

In 239 games with the Pirates, Meares batted .238/.294/.352 with 17 home runs, good for a 65 wRC+. He was worth -1.2 bWAR during his tenure in Pittsburgh, and he was released in August 2001 under the designation of a "permanently injured player".

Good thing the Pirates recouped 70 percent of what they paid him for 2002-03 via an insurance claim, or else that second contract may have actually hurt their bottom line.

5. Tony Armas Jr. - One year, $3.5 million

Going into the 2007 season, the Pirates actually had a solid top three in the rotation: Paul Maholm, Ian Snell, and Tom Gorzelanny.

However, their starting pitching depth was a mess, and thus, they signed Tony Armas Jr. to a one-year deal with the hopes that he'd fill their No. 4 starter role with aplomb, and possibly turn into a valuable, flippable trade chip.

So much for that idea. In his first three starts in a Pirates uniform, he went 0-3 with an ERA of 8.92. He'd deal with recurring forearm injuries from there, moving in and out of the bullpen when he was healthy to produce a 6.03 ERA and -0.5 bWAR in 97 innings.

Naturally, the Pirates declined his mutual option for the 2008 season, allowing him to test free agency (he'd sign with the Mets, struggle badly and retire shortly after). His 2007 campaign with the Pirates stands as the worst of his career by nearly every notable metric.

4. Lonnie Chisenhall - One year, $2.75 million

I came down hard on Scott Olsen for his failure to appear in a game with the Pirates on his contract. Take that story, multiply the salary by five, and you get the saga of Lonnie Chisenhall.

From 2011-18, Chisenhall hit a solid .268/.320/.427 with 64 home runs and 296 RBI for the Cleveland Guardians. Injuries limited him to just 111 games between those latter two campaigns, though he was a versatile player who seemed perfect to fill in at right field while Gregory Polanco recovered from offseason shoulder surgery.

I spoiled the ending already, but suffice to say, Chisenhall did not fill in for Polanco. In fact, it was he who needed to be filled in for. After breaking his hand/wrist in spring training on a hit by pitch, Chisenhall made it all of seven games into his rehab assignment with Triple-A Indianapolis before sustaining a calf injury.

He spent the remainder of the season recovering at home, away from the team. For $2.75 million, he gave the Pittsburgh Pirates organization five hits in Triple-A. A quick search on Twitter for "Lonnie Chisenhall Pirates" will tell you all you need to know about the fanbase's memories of his "tenure" with the franchise.

3. Érik Bédard - One year, $4.5 million

You could genuinely rank Bédard's contract anywhere on this list and it'll feel like the right spot. I have him all the way up at No. 3 simply because of his status with the 2012 team — he was signed as the Opening Day starter for that season.

That didn't work out. In 125 2/3 innings, he compiled a 5.01 ERA (4.07 FIP), accumulating -0.4 bWAR on a team that desperately needed support for 35-year-old ace A.J. Burnett. Bédard also had a nasty habit of taking forever to pitch, with many of the games he started encroaching on the four-hour mark.

In what proved to be yet another lost season by the Allegheny River, the Pirates failed to trade Bédard at the deadline, eating the entirety of his contract as he authored the worst full season of his career.

If you're looking for a silver lining on this signing, Bédard does currently hold the franchise record (tied with Francisco Liriano and Paul Skenes) for the most consecutive strikeouts by a pitcher with seven.

2. Raúl Mondesi - One year, $1.75 million

We have officially entered "all-time bust" territory.

A two-time Gold Glover with the Dodgers earlier in his career, Mondesi signed an affordable one-year deal with the Pirates that also included an $8 million club option prior to his age-33 season.

Things got off to a smooth enough start — Mondesi is part of an exclusive club on this list by virtue of providing the Pirates with a positive WAR total (0.1) — slashing .283/.355/.424 in his first 26 games with the team.

Then, he abruptly left to attend to a civil lawsuit in his home nation of the Dominican Republic. His stay took far longer than anticipated, causing tons of turmoil within the clubhouse. “I’ve played 20 straight years of baseball all year round,” Mondesi said during his hiatus. “I deserve a rest even if it’s only for a few months.”

A "few months" eventually turned into the entire season, and the Pirates were faced with no choice but to release him. He quickly signed with the Los Angeles Angels for the remainder of the campaign... and suffered a season-ending injury eight games into his tenure there.

To call his 2004 season a circus would be the understatement of the century.

1. Derek Bell - Two years, $10 million

At last we arrive at, perhaps, the worst free-agent deal in the history of Pittsburgh sports.

In a weird way, it's sort of a testament to the organization that this is the only eight-figure deal on this list, and some reports actually suggest Bell earned less than $10 million with the Pirates. Still, that's hardly of comfort to fans who vividly remember "Operation Shutdown".

After playing all of 46 games with the Pirates in the first season of his deal (posting a .576 OPS and -1.2 bWAR), Bell came into spring training in 2002 under the impression that the starting right field job was his. When it was revealed to be a competition, Bell offered Robert Dvorchak of the Post-Gazette one of the most iconic quotes in Pittsburgh sports history:

"Nobody told me I was in competition. If there is competition, somebody better let me know. If there is competition, they better eliminate me out of the race and go ahead and do what they’re going to do with me. I ain’t never hit in spring training and I never will... Ask [general manager Dave] Littlefield and ask [manager Lloyd] McClendon if I’m in competition. If it ain’t settled with me out there, then they can trade me. I ain’t going out there to hurt myself in spring training battling for a job. If it is [a competition], then I’m going into ‘Operation Shutdown.’ Tell them exactly what I said. I haven’t competed for a job since 1991."

Derek Bell, Pirates outfielder (2002)

Considering general manager Cam Bonifay had been replaced over the offseason with Dave Littlefield, there was no allegiance to Bell in the organization. The team cut ties with the outfielder in spring training, and he would take his $4.5 million for the 2002 season and run all the way to his now-infamous yacht, the "Bell 14".