4 best (and 4 worst) trade deadline deals in Pittsburgh Pirates franchise history

Ahead of the 2025 MLB trade deadline, the Pittsburgh Pirates have emerged as one of the most obvious sellers on the market.

In what projects to be a buyer-heavy landscape, that should serve the franchise well, even as it looks to offload some of its most talented players.

Given their relative futility over the past few decades, it should come to no one's surprise that the Pirates don't have the strongest trade deadline track record. From giving up on über-talented prospects far too soon to buying underperforming veterans on bloated contracts, the team hasn't always been the best at navigating this time of year.

That being said, Pittsburgh hasn't been completely inept at the trade deadline in its long history, bringing in some franchise icons during the transaction-heavy frenzy. As such, ahead of an important deadline for the team, it seems like a useful activity to recount some of the most important mid-season trades executed by the franchise.

Note that the trade deadline, which began in 1923, used to be set on June 15; it was only in 1986 that the deadline was pushed back to its modern date of July 31.

Thus, the trades listed here only include mid-season deals completed after the beginning of June, which we'll arbitrarily define as the beginning of "trade deadline season". Anything prior to that is too far removed from the hottest part of the rumor mill cycle to justify a placement on this list.

Otherwise, all trades are fair game. So, let's go for a stroll down memory lane and recount the best (and worst) trade deadline deals in Pirates history.

8 most impactful trade deadline trades in Pittsburgh Pirates history

Best: "Mad Dog" lifts Pirates to World Series

Trade: Pirates trade Fred Breining, Al Holland and Ed Whitson to San Francisco Giants for Bill Madlock, Lenny Randle and Dave Roberts (June 28, 1979)

Might as well kick things off with arguably the best trade deadline deal in franchise history.

From the Giants' end of things, this deal wasn't an outright disaster. Breining gave them 4.8 bWAR and a 3.37 ERA through four seasons, mostly out of the bullpen, while Holland finished seventh in NL Rookie of the Year voting in 1980, the same year Whitson was named an All-Star. This was hardly a return package to scoff at.

However, while Randle wouldn't play a game for the Pirates (he was quickly sold to the Yankees for cash), Roberts became an important bullpen piece... oh, and Bill Madlock became a franchise legend.

Already a two-time batting champion prior to the trade, Madlock would go on to win two more in Pittsburgh (1981, 1983). He earned two All-Star appearances with the Pirates, slashing .297/.357/.428 over 801 games with the team.

Of course, the greatest contribution "Mad Dog" provided was in 1979, proving to be instrumental to the "We Are Family" team of destiny. The Pirates went 62-32 after the trade, as Madlock hit .328/.390/.469 with seven home runs, 44 RBI, and 21 steals. He also hit .375 (9-for-24) in the World Series as the Pirates won their fifth (and most recent) championship.

Worst: A premium for Chris Archer

Trade: Pirates trade Austin Meadows, Tyler Glasnow and Shane Baz to Tampa Bay Rays for Chris Archer (July 31, 2018)

The Pirates were long infatuated with Archer — so much so that MLB insider Ken Rosenthal perfectly predicted this trade years prior to its actual completion — and at the time, the deal made some semblance of sense.

Archer, 29 at the time, had 3.5 more years of team control at reasonable salaries, an obvious boon for the historically frugal Pirates. Though he had a 4.31 ERA in 96 innings at the time of the deal, he was an All-Star as recently as the previous season and finished fifth in AL Cy Young voting just three years prior to the trade.

Of course, the deal didn't work out for Pittsburgh, as Archer pitched to a 4.92 ERA in his 1.5 seasons in Pittsburgh. Meanwhile, Meadows became an instant All-Star with the Rays, and Glasnow emerged as a mega-talented pitcher with injury issues before getting flipped to the Dodgers prior to the 2024 season.

Originally included in the deal as a player to be named later (PTBNL), Baz emerged as one of baseball's best prospects over the subsequent seasons, and he's come close to figuring things out with the Rays in recent years, though injuries have limited him from fulfilling his massive potential.

In all, this was a good ol' fashioned swindling by the Rays, and even if it hasn't aged quite as badly as it first appeared, it was a primary motivator in team ownership firing general manager Neal Huntington after the 2019 season.

Best: A trip to the Bay for Brian Giles

Trade: Pirates trade Brian Giles to San Diego Padres for Jason Bay, Oliver Pérez and Cory Stewart (Aug. 26, 2003)

Brian Giles was a brilliant player on a bunch of bad Pirates teams, hitting at least 35 home runs in every season from 1999-2002 despite Pittsburgh never winning more than 75 games in any of those seasons.

With a clear and obvious need for a reset, Pittsburgh flipped Giles for a package headlined by Jason Bay, who would quickly develop into a multi-time All-Star in Pennsylvania.

Bay won NL Rookie of the Year in 2004 and then followed up with back-to-back All-Star campaigns in 2005 and 2006. In parts of six seasons with the Pirates, Bay slashed .281/.375/.515 before getting dealt in a three-team swap that landed the Pirates Brandon Moss and others.

Pérez was no slouch either, emerging as an ace for one glorious season in 2004 (2.98 ERA in 196 innings). He wouldn't quite reach those heights again, but he did spend a prosperous 20-year career in the big leagues, including his four campaigns in Pittsburgh.

It's not like San Diego got completely screwed in this deal either, as Giles played the final seven years of his career on the West Coast and smacked 83 home runs in 833 games for the Friars. It was a long way off from his production in Pittsburgh, but the Padres at least got a quality bat for their troubles.

Worst: Leaving the Bay for peanuts

Trade: Pirates trade Jason Bay to Boston Red Sox for Andy LaRoche, Bryan Morris, Brandon Moss and Craig Hansen (July 31, 2008)

Speaking of that other Jason Bay trade, this was a three-team deal involving the Dodgers and Red Sox that most assuredly did not go the Pirates way.

Bay was sent to Boston, who forked over Manny Ramirez to the Dodgers. In return the Pirates got a group of highly-touted prospects, none of whom panned out the way the franchise hoped.

With the Red Sox, Bay re-emerged as a sensation, accruing a whopping 7.2 bWAR in just 200 games with the franchise, earning an All-Star appearance, Silver Slugger, and seventh-place finish in AL MVP voting for his brilliant 2009 campaign.

Meanwhile, Moss, the core piece of the return, struggled badly in Pittsburgh, slashing .228/.295/.373 in 195 games, accruing -1.2 bWAR. Laroche was no better, earning 0.4 bWAR in 301 games before getting designated for assignment two separate times in 2010.

The ancillary pieces of the return — Hansen and Morris — were hardly noteworthy in their Pittsburgh tenures, the former posting a 6.95 ERA in 22 innings with the franchise and the latter handling 93 2/3 innings (5.03 FIP) before getting dealt to Miami.

Ultimately, this was a failure at an organizational level, a fact Huntington acknowledged years later following the team's stretch of success from 2013-15.

Best: Bobby Bonilla, obviously

Trade: Pirates trade José DeLeón to Chicago White Sox for Bobby Bonilla (July 23, 1986)

I won't lie — I tried hard to find a deal worthy of replacing this one on the list, because this is such an obvious answer. Sometimes, though, Occam's Razor applies, and we just have to accept that the simplest answer is the right one.

After leaving Bonilla unprotected in the Rule 5 draft, the Pirates reacquired the outfielder after his strong half-season debut with the White Sox.

From 1988-91, Bonilla would accrue 17.9 bWAR as the Buccos' cleanup hitter, earning four straight All-Star appearances, three Silver Sluggers, and two top-three MVP finishes (coming in behind Pirates teammate Barry Bonds both times). He would eventually leave for the Mets (and one of the most ridiculous contracts in baseball history), though he was a key member of the back-to-back division champions in 1990 and 1991.

Keeping DeLeon in Pittsburgh was simply untenable at the time, as he went an unthinkable 2-19 in 1985 back during a period when pitching records mattered a great deal. The White Sox would help him turn into a solid starter — he would post a 3.85 ERA in 430 innings in Chicago over the next five seasons — though he hardly lived up to Bonilla's incredible production.

Worst: A sad (Vogel)song

Trade: Pirates trade Jason Schmidt and John Vander Wal to San Francisco Giants for Armando Rios and Ryan Vogelsong (July 30, 2001)

This was Dave Littlefield's first deal as the general manager of the Pirates, and oh boy, does he want this one back.

Schmidt, who simply couldn't get over the hump in Atlanta or Pittsburgh (4.39 ERA in nearly 800 innings with the Pirates), suddenly became unstoppable in San Francisco, earning three All-Star nods, an ERA title in 2003, and back-to-back top-five Cy Young finishes in 2003 and 2004. He also played a key role in the Giants' run to the World Series in 2002, going 2-1 across four postseason starts.

Vander Wal didn't do much in his lone half-season in California, though he did serve as a decent table-setter for old friend Barry Bonds during the first of Bonds' four straight MVP campaigns.

Meanwhile, Rios played 78 games for the Pirates and contributed -0.6 bWAR to the cause. And Vogelsong, despite all his talent, struggled tremendously in Pittsburgh, requiring Tommy John surgery almost immediately after the deal, missing the entire 2002 season. He came back and pitched to a 5.87 ERA from 2003-06, offering the team -2.2 bWAR during his entire first tenure.

What makes this hurt even more: after a stint in Japan, Vogelsong returned to MLB five years later and became an All-Star... with the Giants.

Best: Cruzing out of Los Angeles

Trade: Pirates trade Tony Watson to Los Angeles Dodgers for Angel German and Oneil Cruz (July 31, 2017)

Unlike every other "best" deal here, this one is relevant to the team in 2025! Which, admittedly, is more of an indictment of the team's recent performance in trades than it is a credit to their trade history, but still, this already ranks as one of the smartest trade deadline deals ever executed by the franchise.

In full pursuit of their first World Series title in nearly three decades — one they were ultimately scammed out of thanks to the Houston Astros' trash can scandal — the Dodgers gave up a big, toolsy prospect with a ridiculuous ceiling at just 18 years old for a rental reliever.

In fairness to them, Watson pitched well down the stretch in Dodger Blue, firing off a 2.70 ERA in 20 innings in the regular season and a 2.57 ERA in seven innings in the postseason, ultimately fulfilling his promise as a high-leverage lefty reliever.

The Pirates, meanwhile, made out like bandits, and watched as the 6'7" Cruz developed into one of the loudest and most tantalizing prospects in baseball.

He hasn't quite lived up to his sky-high potential in Pittsburgh, though the flashes have been there. Though he's still working things out on defense as he transfers from shortstop to center field, the Dominican slugger is slashing .242/.316/.441 as of the 2025 All-Star break, and he's well on pace to join the 20-20 club for the second consecutive season.

Owner of the hardest hit ball in the Statcast era, Cruz is still figuring things out at the highest level, but his star is burning brighter than ever. Following his Home Run Derby performance in 2025, Cruz has put himself (and the Pirates) back in the national spotlight.

Worst: Aramis Ramirez, where art thou?

Trade: Pirates trade Aramis Ramirez and Kenny Lofton (and cash) to Chicago Cubs for Matt Bruback, José Hernández and Bobby Hill (July 23, 2003)

Truth be told, this is the trade I always think of when someone asks me to identify a prototypical "bad" Pirates trade. It's hard to pinpoint exactly why, though perhaps its because the Pirates let Ramirez — just as he was approaching the peak of his powers — wreak havoc in the NL Central with the darn Cubs.

Ramirez went on to become a Cubs (and NL Central) legend, earning multiple All-Star nods and down-ballot MVP support throughout his time in Chicago. He gave the Cubs 24.1 bWAR and 239 home runs across parts of nine seasons, establishing himself as one of the better third basemen in franchise history.

And lest you think otherwise, Lofton wasn't a mere throw-in. Like Ramirez, he was instrumental in the Cubs' run to the NLCS in 2003, producing 1.8 bWAR and a .327/.381/.471 slash line in the regular season and a .715 OPS in the postseason that year. As far as rental players go, he was a good one.

For their troubles, the Pirates received Bruback (pitched four games in Triple-A Nashville before being let go), Hernández (-0.4 bWAR in 58 games before being released), and Hill (.689 OPS in 185 games).

A fair trade, this was not.