The Milwaukee Brewers are showing the Pittsburgh Pirates exactly what comes next after a franchise makes a splashy bet on a young star.
Pittsburgh’s April extension for Konnor Griffin - a nine-year, $140 million deal that stands as the richest contract in franchise history - was the kind of move that briefly changed the conversation around the club. For a team long associated with caution at the top of the payroll, it gave fans a rare reason to think differently about where the organization might be headed.
But Milwaukee’s World Series run is underlining the bigger truth: securing one cornerstone is only the opening act.
On Saturday in Game 2 against the Tampa Bay Rays, rookie shortstop Cooper Pratt came through with the go-ahead RBI single in the seventh inning, finishing off a comeback from a four-run hole and pushing the Brewers to a 5-4 win. That gave Milwaukee a 2-0 lead in the series and put it two victories away from its first World Series title.
Pratt’s rise is the part of the story that should land hardest in Pittsburgh. Milwaukee signed him to an eight-year, $50.75 million extension in April before he had even played a major league game, betting on his future rather than waiting for the market to get more expensive. Griffin received a bigger deal that same month, with Pittsburgh locking him in through the 2034 season before he had a chance to fully establish himself at the highest level.
The Pirates and Brewers both deserve credit for seeing the value in securing young talent early. What separates the two, though, is the way that commitment sits inside the rest of the roster.
Pratt did not carry Milwaukee on his own. He also contributed to the early deficit with a first-inning throwing error that helped Tampa Bay get out to a four-run lead.
Still, William Contreras and Garrett Mitchell chipped in with RBI singles, Sal Frelick erased the gap with a sixth-inning home run, and the bullpen covered the final six scoreless innings. That’s a team built to survive mistakes and keep pushing.
That kind of support system is what Pittsburgh still has to build around Griffin.
The Pirates closed 2026 at 82-80, their first winning season since 2018, but they still finished six games short of the National League’s final Wild Card spot. General manager Ben Cherington now heads into an offseason that will say a lot about how serious the organization really is about contending.
There are holes to address. Brandon Lowe, who led Pittsburgh with 35 home runs and 96 RBI, is headed for free agency. The Pirates still need more production against left-handed pitching, more starting pitching depth and more help in the bullpen, even with Mason Montgomery emerging as a late-inning weapon.
The lesson from Milwaukee is plain: paying young stars matters, but it only goes so far if the rest of the roster isn’t being built with equal intent.
The Brewers haven’t assembled this group through big-money free agency alone. They’ve mixed development, trades and long-term extensions into a roster that can carry a lead through October. Pittsburgh has the pieces to chase something similar, with Griffin, Paul Skenes, Jared Jones, Bubba Chandler and Braxton Ashcraft forming a young core worth believing in.
But talent on paper is not the finish line. If the Pirates want Griffin’s extension to mean more than a headline, they have to keep building around him.
The deal was a step forward for a franchise that has faced repeated criticism over its spending. Now Bob Nutting and Cherington have to show that securing Griffin was only the start - not the end - of their commitment to winning.
In Other News...
Paul Skenes Is Taking On A Fight Pirates Fans Should Watch
As the collective bargaining talks simmer around baseball, Paul Skenes has emerged as one of the more notable voices in the room for reasons that go beyond his place in the Pittsburgh rotation. The Pirates right-hander sits on the MLB Players Association executive subcommittee, giving him a seat at the table as the union weighs the next labor fight, and his role has drawn extra attention because his own career is still on the rise.
Skenes has already made clear where he stands on the leagues push for a salary cap, arguing that it would affect not just stars but players at every level, including those on small-market clubs like the Pirates. Even with his current paycheck far below what his future could bring, the bigger issue for him is what the next agreement could mean for the next wave of players entering the game. [Read more 🡒]
Pirates Could Make One Telling Move If Brandon Lowe Leaves
Brandon Lowes future is already becoming part of the Pirates longer-term planning, even though he is still under control through the 2026 season. If he reaches free agency after that year, Pittsburgh could be in the market for a stopgap at second base, and one analyst has floated a familiar kind of move for a team trying to stay flexible while keeping its roster competitive.
Jazz Chisholm Jr. is the name attached to that possibility, after spending 2026 with the Yankees. The fit would make sense on paper as a short-term answer if Lowe walks, but for now it remains only an idea, the kind of offseason speculation that tells you where a front office might look before the market actually opens. [Read more 🡒]
Pirates May Face A Painful Trade Choice To Keep Brandon Lowe
Brandon Lowes looming free agency has already put the Pirates in a familiar spot: weighing a player they would like to keep against the reality of their payroll. Pittsburgh views Lowe as a valuable piece, and his interest in staying only adds to the appeal, but any serious attempt to bring him back figures to test how far the club is willing to stretch.
The problem is less about desire than fit, because retaining Lowe would likely require a meaningful reshuffling of the roster and budget. For a Pirates team that has spent carefully, that kind of decision can quickly force uncomfortable choices, and the front office may soon have to decide whether keeping one impact bat is worth sacrificing depth elsewhere. [Read more 🡒]