10 most expensive contracts in Pittsburgh Pirates history

The Pittsburgh Pirates have never been known for having free-spending habits, handing out just one nine-figure contract in their history. For reference, the Los Angeles Dodgers have seven such players on their 2025 roster alone.

Nevertheless, the team has (reluctantly) stepped up their financial game in recent years, though only on extensions for in-house stars.

Like the hometown Steelers (at least until they signed Aaron Rodgers), the Pirates generally refuse to get involved in free-agent bidding wars. With an eventual extension for Paul Skenes (hey, a guy can dream) eventually going to blow all these deals out of the water, it figures to be a fun time looking back at the largest deals ever handed out by the Pirates.

Note that we'll be ranking these deals in descending order in terms of overall contract value. For contracts with the same monetary total, we'll use average annual value (AAV) as the tiebreaker.

Pittsburgh Pirates' Largest Contracts: Honorable Mentions

These five players signed the next-largest deals in franchise history, and the meager totals on their contracts foreshadow the upcoming deals in the top 10. Like we said above: the Pirates revel in their frugality.

15. Jason Bay - 4 years, $18.25 million (2005)

14. Jack Wilson - 3 years, $20.2 million (2006)

13. Felipe Vázquez - 4 years, $22.5 million (2018)

12. Kevin Young - 4 years, $24 million (1999)

11. Josh Harrison - 4 years, $27.3 million (2015)

For the most part, these deals worked out in Pittsburgh's favor.

Jason Bay won NL Rookie of the Year in 2004, prompting his extension, and subsequently became a multi-time All-Star in Pittsburgh before getting traded in a three-team swap that landed Brandon Moss and others in Pennsylvania.

Jack Wilson dealt with some injuries but was generally a great defender with some offensive upside before getting traded to Seattle in 2009. Young struggled after signing his extension, though he did finish second in franchise history in home runs by a first baseman with 128 (Willie Stargell is first). As for Harrison, the recently-retired fan favorite made a second All-Star game appearance in 2017 after signing his deal, and he remains one of the better Pirates players of the 21st century.

Vázquez's story is better left unsaid, and the Pittsburgh closer was rightly forced out of baseball.

The biggest takeaways here: none of these deals were signed after 2018, and only two were inked after 2006.

Also, note the length on these contracts. Part of the reason the Pirates simply don't swim in the deepest waters of the free agency pool is because they are unwilling to hand out deals longer than four or five years (besides a few exceptions on in-house extensions). In an MLB environment increasingly leaning toward exceptionally long, low-AAV deals for star players, Pittsburgh simply can't compete until and unless it pushes the 10-year barrier in negotiations.

Assuming that isn't going to happen anytime soon, though, Pirates fans will have to settle for a small-market operation.

Now, on to the 10 largest deals in Pittsburgh Pirates history.

10 largest contracts in Pittsburgh Pirates franchise history

10. Starling Marte - 6 years, $31 million (2014)

Marte was a Top 100 prospect (and Futures Game participant) prior to making his debut with the Pirates in 2012, and after making a strong impression in his first cup of coffee in the big leagues, he broke out during the 2013 season.

Accruing 5.1 bWAR on the back of 41 steals, a .784 OPS and great defense in left field, Marte established himself as a core member of a Pirates team on the rise. Pittsburgh made the playoffs for the first time in 21 years that season, with Marte and NL MVP Andrew McCutchen proving to be the foundation for the future.

Thus, Bob Nutting authorized a $31 million payment to Marte, buying out all of his arbitration years and a free-agent campaign. Marte was generally great as a Pirate, accruing a .287/.341/.452 slash line, 108 HR, 420 RBI, and 239 stolen bases while winning two Gold Gloves (2015-16) and earning one All-Star appearance (2016).

An 80-game suspension in 2017 for PED usage dimmed his star greatly, though, and by the end of the 2019 season, the Pirates and Marte were ready to move on from each other. The team dealt the outfielder to the Arizona Diamondbacks in exchange for Liover Peguero, Brennan Malone, and international bonus pool signing money in January 2020.

9. Francisco Cervelli - 3 years, $31 million (2016)

Originally acquired in a one-for-one deal with the New York Yankees, Francisco Cervelli immediately took over Russell Martin's stead as the starting backstop on a contending team and won over Pirates fans in a flash.

Playing in a whopping 128 games behind the dish in 2015 (130 total appearances), Cervelli accrued 3.5 bWAR while slashing .295/.370/.401 for a team that won 98 games. He did allow an obscene 101 stolen bases — leading the majors that year by a significant margin — but the rest of his contributions were too important to pass up on.

Thus, the Pirates handed Cervelli a one-year extension prior to 2016, though they quickly gave amended that to the three-year, $31 million extension that lands him on this list. In parts of five seasons with Pittsburgh, Cervelli posted a .735 OPS while hitting 26 home runs, thriving in his first (and only) chance to be the undisputed starter behind the plate for a team.

Unfortunately, Cervelli had a history of concussions, and by 2019 (the final year of his deal), he absorbed the sixth of his career. That proved to be the breaking point for both the catcher and the franchise, and the Pirates released Cervelli on August 22, 2019.

8. Gregory Polanco - 5 years, $35 million (2016)

Oh boy. This one hurts.

"Polanco Watch" was a phenomenon in the baseball world in 2014, as 22-year-old Gregory Polanco put the whole sport on notice with his absurd start in Triple-A Indianapolis (.328/.390/.504). At long last, the Pirates yielded to the raucous calls from fans, giving the Dominican outfielder his first taste of MLB action on June 9, 2014, following an injury to second baseman Neil Walker.

From there, Polanco became a sensation. He tied Roberto Clemente's franchise record of consecutive games with a hit to start a career (seven) before breaking it on June 18. He experienced a mini-breakout in 2015, accruing 2.5 bWAR, and that was enough to convince the Pirates to hand him a five-year, $35 million extension.

From there... well, things didn't go according to plan.

He dealt with injuries seemingly every year after, including a bout with Covid-19 in 2020. In parts of eight seasons with Pittsburgh, Polanco appeared in 823 games, posting a .718 OPS with 96 home runs, 362 RBIs and 98 steals. He was released on August 28, 2021.

7. Francisco Liriano - 3 years, $39 million (2014)

This contract has become somewhat of a meme amongst Pirates fans, as it still (somehow) stands as the largest free-agent expenditure in franchise history.

After oscillating between brilliant performances and blunders in Minnesota, the Pirates gave Liriano a two-year deal in free agency in 2013... twice. They had to void the first contract because he broke his (non-throwing) arm while playing with his kids over Christmas.

Luckily, Liriano came back stronger than ever, pitching to a 3.02 ERA in 161 innings as the de facto ace of the staff, and he twirled a gem in the Wild Card Game against the Cincinnati Reds, allowing just one run in seven innings as the Pirates advanced to the NLDS (where they lost in five to the Cardinals).

After another strong performance in 2014, the Pirates gave Liriano a new three-year deal in free agency (the one that landed him on this list), though a great 2015 campaign didn't mean much, as the Pirates' contention window closed the following season. Midway through his deal in 2016, the team sent him to Toronto (along with two prospects) for Drew Hutchinson.

6. Brian Giles - 6 years, $45 million (2000)

After acquiring Giles for Ricardo Rincón prior to the 1999 season, the outfielder developed into one of the best players on one of the worst teams in the National League.

The Pirates never won more than 75 games in a season when Giles was around, though that didn't stop him from becoming a multi-time All-Star. The Pirates rewarded him handsomely for a 6.7 bWAR, 1.032 OPS season in 1999 with a $45 million extension, annointing him and Jason Kendall as the faces of the franchise. At the time of the deal, Giles became the highest-paid player in franchise history.

While he was a force to be reckoned with — he hit at least 35 home runs in every season from 1999-2002 — he never finished higher than 13th in NL MVP voting, a reflection of the team's dismal of affairs around him.

In 715 games in Pittsburgh, Giles hit .308/.426/.591 to go along with 165 HR and 506 RBI. During the stretch run of the 2003 season, he was traded to the Padres for Jason Bay, Óliver Pérez, and minor leaguer Corey Stewart.

5. Andrew McCutchen - 6 years, $51.5 million (2012)

He may not be Honus Wagner, Roberto Clemente, or Willie Stargell, but as far as legendary Pirates go, Andrew McCutchen deserves to be in the discussion.

By 2009, McCutchen had emerged as one of the top prospects in baseball, and despite an abbreviated 108-game debut that year, he finished fourth in NL Rookie of the Year voting. He would go on to improve in every season after that, peaking in 2012 with a .327/.400/.553 batting line to go along with 31 homers, 20 steals, and a Gold Glove. He finished the year as the NL hit king and third in MVP voting.

Luckily, the Pirates had him under wraps on his very team-friendly extension, and he won MVP the following year. He would go on to earn five consecutive All-Star nods, four consecutive Silver Slugger awards, and four consecutive top-five MVP finishes between 2011 and 2015.

As the Pirates fell out of contention following the 2015 season, McCutchen, despite public wishes to remain a Pirate for life, became the subject of incessant trade rumors. His first tenure in Pittsburgh ended when he was traded to the San Francisco Giants for Kyle Crick, Bryan Reynolds, and $500,000 of international bonus slot money.

He's since returned to the Steel City and, by all accounts, he'll finish his career with the Pirates. Eventually, his No. 22 will be memorialized alongside Wagner, Clemente, and Stargell in PNC Park.

4. Jason Kendall - 6 years, $60 million (2000)

"The Kid" was a late-90s sensation in Pittsburgh, earning All-Star appearances as a rookie in 1996 and again in 1998, establishing himself as one of the best catchers in the National League.

Like Brian Giles, as the team prepared to move into its new state-of-the-art home, PNC Park, then-owner Kevin McClatchy made it clear the team would do whatever it took to keep its stars in Pittsburgh. Funny enough, Kendall rejected the same six-year, $60 million offer he would sign in 2000 once the team agreed to defer just five percent of the contract.

Thanks in part to Giles' decision to defer a much larger part of his own deal, Kendall was able to become the first Pirates player with a contract north of $50 million in total value, as well as a $10 million AAV. He never had the MVP breakout ownership was hoping for, but he was still one of the best players from a downtrodden era in the franchise's history.

In nine years with Pittsburgh, Kendall hit .306/.387/.418 with 67 HR and 471 RBI. His time with the Pirates came to an abrupt end when the Oakland Athletics acquired him following the 2004 season for Mark Redman, Arthur Rhodes and cash.

3. Ke'Bryan Hayes - 8 years, $70 million (2022)

You'll notice a running them with our top three entrants: they all signed their deals after 2020, and they're all currently on the team (as of July 2025).

Hayes has had a rollercoaster career since emerging as a consensus top-10 prospect prior to the 2021 season. He's established himself as one of the premier defenders in all of baseball — breaking up Nolan Arenado's historic monopoly on third base Gold Gloves in 2023 — though he's never found any consistency at the plate.

The Pirates' No. 1 draft choice in 2015, Hayes agreed to his deal after pairing his brilliant debut in 2020 with a regression-filled 2021 campaign. Since then, he's been up and down at the plate, posting a 100 wRC+ in 2023, but a sub-65 mark in both of the following seasons.

Hayes' contract runs through the 2029 season with a 2030 club option for $12 million (when he'll be 33), though recent trade rumors suggest he may not be long for Pittsburgh.

2. Mitch Keller - 5 years, $77 million (2024)

Another member of the likely-to-be-traded-soon club, Keller's $15.4 million AAV is the largest the Pirates have ever handed out at as of July 2025.

He signed his $77 million extension following his lone All-Star campaign in 2023 when he delivered a 4.21 ERA in 194 1/3 innings as the undisputed ace of the staff. He's since stepped into the No. 2 role following the emergence of all-universe starter Paul Skenes, but his contributions have been more than valuable enough to make his contract a bargain.

Through the first half of the 2025 season, Keller has given the Pirates a 4.45 career ERA in 150 starts, proving to be a high-value innings eater for a rebuilding squad. He's never evolved into a Cy Young contender, but he's been a remarkably consistent presence in a difficult era of transition.

With Jared Jones and Bubba Chandler on their way to back up Skenes in the Pirates' rotation, Keller may soon become superfluous for a penny-pinching squad. If he is dealt, he'll bring a haul back to Pittsburgh, though his steady hand atop the pitching staff won't be soon forgotten.

1. Bryan Reynolds - 8 years, $106.5 million (2023)

At long last, we arrive at the lone nine-figure deal in Pirates history.

Originally acquired in the Andrew McCutchen trade with the San Francisco Giants, Reynolds' extension negotiations were as tenuous as they were public, and after some posturing for a trade, the outfielder eventually agreed to put pen to paper on a $106.5 million deal ($100 million in new money at the time).

He's been a multi-time All-Star (2021, 2024) in Pittsburgh, and even as he works through the worst major league season of his career in 2025, Reynolds remains one of the best players on a talented young team.

From his debut in 2019 through 2024, Reynolds accrued 19.6 bWAR for the Pirates, slashing .276/.352/.470 with 122 home runs and 411 RBI. He should remain a staple in the lineup as the organization pushes toward its next window of contention.