Copy of OOTP 27 Pittsburgh Pirates Rebuild — 2028–29 Offseason: A New Look for the Champs
A 128–34 season, a third straight pennant, and our second World Series title in three years. There was plenty to like about the team that finished 2028. Keeping the whole group together was another matter.
We head toward 2029 with a new shortstop, a new catcher, a new right fielder, and a different ninth-inning plan. Some familiar faces are gone, several others have long-term deals, and the farm system gives us another reason to keep an eye on what comes next. Apparently winning the World Series does not get you a quiet winter.
Table of Contents
One More Look at the Hardware
Before getting into who left, the championship group deserves its awards. SP Paul Skenes (80/80) took every first-place vote for the NL Cy Young, and LF/DH Shalin Polanco (48/50) did the same in the Rookie of the Year race.
SP Paul Skenes (80/80) 32 G, 210.1 IP, 26–1, 1.71 ERA, 260 K, 46 BB, 0.79 WHIP
LF/DH Shalin Polanco (48/50) 143 G, .265/.357/.524, 29 HR, 80 RBI, .881 OPS
Skenes was about as close to automatic as we could ask for. Polanco gave us a rookie season worth building around, and we made sure his winter included more than a trophy.
2B Termarr Johnson (58/59) and SS Bo Bichette (53/53) won Silver Sluggers, and I picked up NL Manager of the Year. Bichette earned his award as a Pirate, even though he will be wearing another uniform when we get going again.
2B Termarr Johnson (58/59) 153 G, .278/.387/.472, 22 HR, 80 RBI, .859 OPS
SS Bo Bichette (53/53) 111 G, .265/.319/.477, 16 HR, 74 RBI, .795 OPS
Detmers finished second in Cy Young voting. Young was runner-up for Reliever of the Year, De La Paz finished fourth, and Severino placed third for Rookie of the Year. Skenes, Johnson, and Alcantara finished fourth, seventh, and eighth in MVP voting. No Gold Gloves this time, but there was still plenty of hardware coming back to Pittsburgh.
Henderson Is the Headline
The biggest move came December 2, when SS Gunnar Henderson (75/75) signed for 10 years and $482 million. The final $55 million season is a team option, and his salary for 2029 is $40 million. We also gave up a third-round pick in compensation.
The other major league free-agent addition was RP Bradgley Rodriguez (47/48) on a three-year, $4.3 million deal. We also added RP James Norwood (46/46) on a minor league contract with a $750,000 bonus, plus minor league deals for SP Kutter Crawford (46/46) and RP Reggie Crawford (41/43). They give us additional pitching options as the season gets underway.
Four Trades Change the Shape of the Team
November 15 — A different catching tandem. We sent C Henry Davis (58/59) and SS Wyatt Sanford (42/49) to Baltimore for C Creed Willems (55/55), and minor leaguers RF Chris Boyd (41/60), RP Michel Otanez (44/44), and SS Diego Benitez (36/42). Willems gives us a replacement behind the plate at $780,000 for 2029, and Boyd adds an upper-minors outfielder to the system.
November 15 — Rotation depth becomes an everyday outfielder. SP Jared Jones (55/55), C Art Gonsalez (32/45), and RHP David Matoma (42/45) went to Minnesota for RF Emmanuel Rodriguez (55/65), RHP Luis Garces, and RP Giomar Diaz (43/43). Rodriguez steps into right field, while Crossland gets his opportunity in the rotation.
RF Emmanuel Rodriguez (55/65) 148 G, .235/.352/.412, 18 HR, 71 RBI, .764 OPS
The average from his Minnesota season is not going to jump off the page, but 86 walks helped produce that .352 OBP. At $780,000 for 2029, there is a lot to like if he can build on that production.
November 23 — Bichette heads to Detroit. We sent SS Bo Bichette (55/55), LF Jorge Soreni (28/46), RHP Zander Mueth (36/45), and CF Hayden Yost (35/38) to the Tigers for LHP Yordy Herrera (50/50), OF Cris Rodriguez (36/49), 2B Ryan Wynn (33/48), and 2B Franyerber Montilla (39/44). Herrera takes over as closer. Henderson's signing nine days later filled the opening at shortstop.
December 23 — Another depth move. Otanez's stay was short: he went to the Cubs with CF Gabriel Rodriguez for 2B Danny De Andrade (42/46).
That is three familiar contributors gone from the championship team. We have replacements in place, but catching, right field, the rotation, and the ninth inning will all have a different feel.
Keeping Part of the Core Together
The trades were only half the story. We also signed four extensions:
The Other Departures—and Changes Behind the Scenes
We did not offer arbitration to RP Yennier Cano (48/48), CL Danny Young (47/47), and RP River Ryan (47/47). 3B Brendan Donovan (48/48), C Willson Contreras (47/47), 3B Zach McKinstry (44/44), and SP Austin Krob (37/37) also left for free agency. Young's departure is the one that stands out after his second-place finish in reliever of the year voting; he signed with St. Louis for one year and $5.4 million. Ryan joined the Dodgers for one year and $1.96 million.
Three bullpen arbitration cases went to hearings. RP Robert Garcia (45/45) received the team's $2.2 million figure, while RP Dedniel Nunez (45/45) won $2,103,300 and RP Abner Uribe (47/47) won $2,062,800. Together, those hearings account for $6,366,100 in 2029 salary.
In the front office, Ben Cherington left to become the White Sox GM, and Charlie Romero joined us as assistant GM on a four-year deal at $1.1 million annually. I signed my own extension as well during the offseason, which runs four years at $1.9 million per season. Down in the FCL, Julian Gonzalez replaced retiring hitting coach Darrell Sherman. Gonzalez is said to be a legendary hitting coach.
We also completed 26 minor league extensions and 25 automatic renewals, protected several prospects, and made no Rule 5 selection. Nobody was taken from us in the Rule 5 draft either.
How the 2029 Roster Comes Together
After all those moves, we still have a roster that should be capable of making another run. It just looks quite a bit different from the group that finished off Baltimore. Henderson gives us a new centerpiece, Rodriguez gets an important spot in the lineup, and several younger players will have a chance to take on bigger roles.
The Everyday Lineups
Against righties, Johnson and Henderson set the table, with Rodriguez getting the first chance to hit third ahead of Mayo. There is plenty of left-handed hitting in this group—six of the nine starters—and having Alcantara and Suwinski batting seventh and eighth gives us some familiar production near the bottom of the order. Alcantara drove in 133 runs last season, so that is a pretty good bat to have waiting down there.
The lineup changes quite a bit against lefties. Ford takes over behind the plate and leads off, Mayo moves across the diamond to first base, Severino becomes the DH, and Brannigan starts at third. Polanco and Willems move to the bench, giving us five right-handed bats in the starting nine. Johnson drops to ninth, while Henderson and Alcantara handle the middle of the order.
Ford leading off against lefties is one of the more interesting things to watch. We will need him to get on base for Mayo, Henderson, and Alcantara. Rodriguez also stays in the lineup against both sides, so he will have every opportunity to establish himself as an everyday contributor.
The Bench
1B Tyler Locklear (48/48) and LF Slade Caldwell (45/52) round out the position-player group. Locklear gives us another right-handed option at first base or DH, while Caldwell provides another outfielder and a chance to work a younger player into the mix.
The other two bench spots change with the opposing starter: Ford and Brannigan sit against righties, while Willems and Polanco sit against lefties. That gives us 13 position players, including two catchers and several ways to rearrange the infield without making a roster move.
The Pitching Staff
Skenes and Detmers are back at the top after finishing first and second in Cy Young voting. That is a pretty good place to start, even if expecting another 26–1 season from Skenes might be asking a little much.
Crossland is the biggest change. With Jones gone, he enters the rotation in the third spot and gets a chance to turn that potential into a full season of starting work. Warren and Gilbert complete the five-man group, giving us experience behind the younger arm. Detmers is the only left-handed starter.
For me, Crossland is one of the most important players on this roster. We know what the top two can do. If he takes a step forward, the rotation has a chance to absorb the Jones trade without losing too much.
As for the bullpen, Herrera gets the ninth inning, with Uribe and De La Paz handling setup and high-leverage work from the seventh inning onward. That leaves a fairly clear late-game plan, but replacing Young is still one of the bigger questions heading into the season.
We are carrying five lefties and three righties in the bullpen. That gives us plenty of options against left-handed hitters, although we will need the group to handle right-handed bats as well. Rodriguez and Lobo add new options, while Nunez, Garcia, and Soto give us returning arms around them. There is no dedicated long-relief role in the current setup, so covering a short start will be something to keep an eye on.
Where We Stack Up Around the Diamond
OSA gives us five positions in the top ten, led by SP Paul Skenes (80/80) at No. 1 and SS Gunnar Henderson (75/75) at No. 2. That is a pretty good foundation for another run. The rankings also make it clear where we have something to prove.
The strength is easy to see: shortstop, third base, center field, catcher, and the top of the rotation. Rodriguez sits just outside the top ten in right, with Johnson close behind at second. We have enough quality spread around the field that this does not need to be a one-man offense.
First base and left field both come in 21st. Those are spots to monitor, although the first-base ranking only tells part of our story: Mayo moves there against lefties while Severino shifts to DH. Suwinski will have a chance to outperform his ranking, but after a seven-year extension, we will certainly be watching the return on that commitment.
The biggest question is the ninth inning. CL Yordy Herrera (49/49) ranks 30th, and that is a tough starting point after letting Young go. It does not mean Herrera cannot succeed. It does mean I want to see him establish himself before treating the closer situation as settled. Garcia's 14th-place relief ranking offers a more encouraging comparison elsewhere in the bullpen.
The Farm System: 25th, with Work to Do
We enter this season with the 25th-ranked farm system. Last year's offseason recap listed us 13th, so the published ranking is twelve places lower this time around. The rankings alone cannot tell us how much of that comes from promotions, trades, or changes in how the players are evaluated, but replenishing the system needs to stay on the to-do list.
Our Top 20 Prospects
Adding to the Next Wave
International signings SS Mario Perez (24/67) and 2B Gabe Romero (23/58) sit outside this top ten, at Nos. 14 and 23 respectively on the supplied list. Perez's displayed 75 power and 70 eye make him particularly interesting, while Romero shows 60 power and 60 eye. Both are 16 and assigned to the international complex, so they are long-term development projects. Their overall/potential pairs come from their signing-era scouting messages.
For now, the system has some arms to develop and plenty of outfield names to sort through. What it needs is more players forcing their way into the picture. With the major league payroll scheduled to climb, producing affordable contributors will matter just as much as improving that 25th-place ranking.
Around the League: The Cubs Sell, October Rivals Add
The biggest division story was Chicago moving several familiar names. The Cubs sent SP Justin Steele (53/53) to Colorado, SP Andrew Abbott (46/46) to Miami, 2B Nico Hoerner (47/47) to San Diego, and RF Kyle Tucker (59/59) to Philadelphia. That is a lot of turnover in one winter, although nobody gets to collect the wins on paper.
Colorado also added SP Hunter Greene (73/75), LF Heliot Ramos (50/50), and 1B Kristian Campbell (58/58). Arizona brought in 2B Willy Adames (45/45) and SP Bryan Woo (54/54). Those are meaningful additions for two clubs that took us to deciding games last October.
Elsewhere, SP Gerrit Cole (57/57) joined Tampa Bay for roughly $97 million over three years, SP Kodai Senga (53/53) went to Cleveland for three years and $66 million, and 1B Freddie Freeman (57/57) re-signed with the White Sox for two years and $46.4 million. Philadelphia added 1B Christian Yelich (51/51) alongside Tucker, while former Pirate CF Oneil Cruz (50/50) agreed to a four-year, $61.6 million extension with the Angels.
Miguel Cabrera and Zack Greinke entered the Hall of Fame on their first ballots with 99.7% and 81.4% of the vote. Ryan Braun fell short at 67.1%. Baltimore fired Brandon Hyde after reaching the World Series, the Yankees dismissed Aaron Boone and Brian Cashman, and Minnesota moved on from Jeremy Zoll. The league also explored expansion before cancelling those plans, though plans still remain on the table.
What I’ll Be Watching in 2029
Henderson will get the attention, but I am just as interested in how the less expensive changes work out. Can Willems and Ford give us steady catching? Does Rodriguez take another step in right field? Can Crossland turn his rotation opportunity and spot starts in 2028 into a full season of useful starts?
Then there is Herrera. With a new closer and several familiar bullpen arms gone, protecting the late innings will be one of our first real tests. Behind the big club, we need more prospects pushing for jobs as those future salaries come due.
We have enough here to make another run. We also have enough new faces that I would like to see a few games before penciling in another parade. The championship banner is paid for; the next few years of this roster are another story.
Thanks for reading as we will check back in after the first 41 games!
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