Pittsburgh Pirates: Assessing the Best Free Agent Signings of the Past 25 Years

In this, the 25th offseason of the 21st century, Pirates general manager Ben Cherington has been the subject of criticism (or at least questioning) as fans clamor for a big free-agent signing, but how does Cherington’s time at the helm compare to his predecessors?

As a small market, Pittsburgh often does not figure as a major mover or shaker during the offseason, but like every MLB franchise, the Pirates have enjoyed a few surprising pickups and lamented their fair share of busts. Starting with the 1999-2000 offseason, I attempted to assess the value of each free-agent signing with a particular emphasis on on-field performance and return on investment.

Relatively few impactful free-agent signings occurred in the last few years of Cam Bonifay's reign, so the focus here is on Cherington, Neal Huntington, and Dave Littlefield. To qualify for this list, the signing had to have occurred between the end of the prior season and Opening Day (approximately April 1), and if a player re-signed with the team after exploring the free-agent market, I considered all consecutive years as one signing.

This exploration resulted in a few surprises and several blasts from the past. Without any further ado, I present the Pirates’ best and worst free-agent signings of the 21st century.

No. 1 The Ben Cherington Era (Nov. 2019 - present)

Jose Quintana (Nov. 2021, 1 year, $2 million)

Cherington’s reuses this script every offseason: a mid-career starter signed to eat innings and mentor young pitchers. Compared to the more recent contracts with Rich Hill and Martin Perez, though, the Quintana deal was a steal.

Quintana turned in his best performances since an All-Star campaign with the White Sox in 2016. He ranked in the top 10 in ERA, games started, and FIP, and he led MLB in home runs allowed per nine innings. Quintana’s four-seamer had a resurgence and ranked as the 20th most effective pitch in the Majors based on run value.

The cherry (or Cherington) on top of this signing, though, was its yield. With the Pirates sitting at 47-58 and the Trade Deadline approaching, Pittsburgh flipped Quintana and reliever Chris Stratton to St. Louis for two highly regarded, young, controllable players: Johan Oviedo and Malcolm Nunez. 

Before undergoing Tommy John surgery in late 2023, Oviedo, who won’t hit free agency until 2028, racked up 2.9 WAR and displayed one of the most devastating sliders in the game. Nunez rose quickly through the farm system, ending 2023 with Triple-A Indianapolis. He currently ranks as the Pirates’ No. 22 prospect and will likely make his Major League debut in 2024. Quintana, meanwhile, signed a $13 million, two-year deal with the Mets before 2023 and missed half of that season due to injury.

Carlos Santana (Nov. 2022, 1 year, $6.75 million)

Even in a relatively down year for the first baseman, Santana provided both tangible and intangible value. His fielding and leadership steadied the rest of the infield, who averaged 24 years of age. He also turned in quality at-bats, ranking above the 75th percentile in chase, K, and walk rate.

The true value of this signing, somewhat like Quintana’s, relies on the outcome of the trade that moved Santana to Milwaukee in late July 2023. In exchange for the veteran first baseman, Pittsburgh received 18-year-old shortstop Jhonny Severino. As of now, he has yet to play a full season of pro ball, but his early results in the Minors have been exciting. Ultimately, Pirates fans will have to wait several more years to assess whether the No. 30 prospect in the system pans out.

No. 2 The Neal Huntington Era (Sept. 2007 - Oct. 2019)

David Freese (March 2016, 1 year, $3 million; subsequently extended for 2 years, $11 million)

Freese contributed two and a half solid years both in the field and at the dish. He excelled against lefty pitching (.308 average in his time with the Pirates), and he provided a sure hand at third base. In 2017, Freese’s range factor per game at third of 2.48 ranked second only to Nolan Arenado.

At the waiver deadline on August 31, 2018, the Pirates traded Freese to the Dodgers. The move saved some cash, as Freese had a $6 million option for the 2019 season, and Pittsburgh received an exciting young prospect, Jesus Valdez. The infielder showed some pop in the Minors and rose to Double-A Altoona before being released following the 2021 season.

Francisco Liriano (Feb. 2013… it’s complicated)

Liriano was in line for a two-year, $12.75 million contract before he broke his right arm “attempting to scare his kids.” The injury resulted in a revised one-year, $1 million deal with a vesting option for 2014, and boy, did Liriano earn every additional penny. In 2013, the lefty won 16 games and propelled the Pirates to a Wild Card victory over the Reds in their first postseason appearance since 1992.

Liriano experienced mixed success in 2014 and rejected Pittsburgh’s qualifying offer at the end of the season. Ultimately he returned to the Pirates on a three-year, $39 million deal. Like Huntington’s other notable free-agent pickups, Liriano was dealt as a cost-cutting measure, and like Huntington’s other salary-dumping moves, the trade returned little on-field value.

Along with Liriano, the Pirates sent former first-round pick Reese Mcguire and outfield prospect Harold Ramirez to Toronto for Drew Hutchison. Hutchison saw limited time in the Majors in 2016 and spent 2017 with Indianapolis before being released by the club. Meanwhile, Ramirez has turned into a serviceable outfielder and DH with good bat-to-ball skills.

Russell Martin (Nov. 2012, 2 years, $17 million)

Of all of Huntington’s moves, this signing provided the most immediate and long-term value, although that future payoff took some time to develop. In the short-term, Martin provided two years of solid offensive and defensive value. His two homers rallied the Pirates past the Reds in the 2013 National League Wild Card Game, and he led both the 2013 and 2014 teams in defensive WAR.

Pittsburgh tried to retain Martin’s services for 2015 and beyond, issuing him a qualifying offer. Martin turned down the one-year, $15.3 million contract and took his talents to Toronto. While it seemed at the time that the Pirates lost a high-impact player for no immediate return, the qualifying offer allowed Pittsburgh to gain a second first-round pick in the 2015 Draft. Those two picks? Kevin Newman and Ke’Bryan Hayes.

Jeff Suppan (Jan. 2003, 1 year, $500,000; club option for 2004, $4 million)

This is it. Perhaps the most impactful free-agent signing for Pittsburgh in the early 21st century. Suppan had been a durable, if homer-prone, starter with a career ERA of 5.03, but the Pirates unlocked his potential. Over the first four months of the 2003 season, Suppan fired three complete games (two shutouts) and logged a 3.57 ERA. Littlefield then flipped him in a five-player deal with the Red Sox.

The two players that Pittsburgh received from Boston, Mike Gonzalez and Freddy Sanchez, helped guide the franchise through the mid-2000s. Gonzalez had an outstanding season in 2004 as a full-time member of the bullpen, posting a 0.877 WHIP. His best seasons came in Pittsburgh, and he moved to the Braves as a piece in the Adam LaRoche deal. Sanchez became a three-time All-Star and won the batting title in 2006.

Conclusion

Each 21st century Pirate general manager will have his detractors. Littlefield’s six-year tenure featured several one-year rentals (Roberto Hernandez, Kenny Lofton, Sanders, etc.), whose on-field success garnered trade interest but ultimately provided little in the way of long-term returns.

Huntington gambled on prospects at the trade deadline, but few of these panned out. Similarly, Cherington has shown no hesitation in buying veterans and betting on youth. It may be 2049 before we get a true sense of the impact of this year’s offseason moves.