The Milwaukee Brewers and Tampa Bay Rays are headed for the 2026 World Series, and for the Pittsburgh Pirates, that creates an uncomfortable backdrop.
Both clubs have built contenders as small-market teams, and both are on Major League Baseball’s list of 12 teams that would have to boost spending under the league’s proposed salary floor. The Pirates are there too.
That’s a tricky look for a league trying to sell players on a major economic reset as the path to competitive balance.
Under MLB’s first collective bargaining proposal, teams would face a $171.2 million salary floor and a $245.3 million hard cap starting in 2027. Based on 2026 Opening Day payrolls, MLB says 12 teams would need to add a combined $617 million to meet the floor.
Pittsburgh opened the season at about $122.6 million in MLB’s accounting, with Milwaukee at $130.9 million and Tampa Bay at $108.2 million. Yet Milwaukee rolled to a franchise-record 103 wins and swept the Los Angeles Dodgers in the National League Championship Series, while the Rays won 98 games and are headed to their third World Series since entering MLB in 1998.
The Pirates, by comparison, finished 82-80 for their first winning season since 2018 and still missed the postseason.
The broader point is hard to miss: if two clubs operating in the same financial neighborhood as Pittsburgh can reach the sport’s biggest stage, how much can be blamed on payroll alone?
This will be the first World Series in the 21st Century featuring two teams in the bottom half of MLB in payroll
h/t @mollyjgeary @spotrac @baseballpro pic.twitter.com/vTPum5scfy
- Lev Akabas (@LevAkabas) October 20, 2026
That doesn’t mean Milwaukee and Tampa Bay undercut MLB’s case for a salary floor entirely.
There’s still a real difference between building a contender through scouting, development and smart trades and having the cash to keep that kind of success going. In theory, a floor paired with meaningful revenue-sharing reform could help smaller-market teams keep homegrown players, shop more aggressively in free agency and avoid constant turnover.
But MLB’s proposal also includes a hard ceiling, something the players’ union has long resisted because it could limit earning power. And the Brewers and Rays getting this far invites another question: are smaller-market owners unable to spend more, or simply unwilling to do it unless they’re forced?
Pittsburgh does not need Dodgers-level money to win. Milwaukee and Tampa Bay have already proved that much. What the Pirates should be wondering is why those clubs are making limited resources count while they keep coming up short.
A salary floor might eventually push Nutting to spend more. It will not suddenly fix roster building, hitter development or the quality of the front office’s investments.
So as two teams with supposedly limited means prepare to play for a championship, Pittsburgh’s real issue looks less like the system around it and more like what the franchise has done within that system.
In Other News...
Pirates Suddenly Have A Shortstop Puzzle They Can't Ignore
The Pirates suddenly find themselves with a good problem on the infield side: a wave of shortstop talent that gives the organization real depth, but also a looming question about where everyone is going to play. Johan De Los Santos, Konnor Griffin, Wyatt Sanford and Aiden Ruiz all sit in that pipeline, giving Pittsburgh multiple young options at a position where development is usually as much about opportunity as it is about skill.
De Los Santos added to his stock with a strong 2026 season that earned him Rookie-Level Player of the Year honors, and the organization now has to map out how to keep his progress moving without clogging the path for the others. For a club trying to build toward the majors, the challenge is no longer finding shortstops - it is making sure there are enough innings, at-bats and defensive reps to go around. [Read more 🡒]
Paul Skenes May Have One Fix That Changes Everything For Pirates
Paul Skenes went from Cy Young winner to a pitcher looking for answers in 2026, and the clues point to something more specific than just a rough stretch. His fastball sat a little differently, his changeup lost some of its bite, and the overall package did not look like the one that made him one of baseballs most overpowering arms in 2025. Skenes has already pointed to fatigue and the World Baseball Classic as possible reasons, but the sharper evidence suggests the problem may have started with the way he was delivering the ball.
The most intriguing part is how one subtle adjustment could ripple through everything else he throws. A slightly higher arm slot may have changed the movement on his changeup enough to make it far less effective, especially when left-handed hitters were in the box, which helps explain why the pitch no longer played like a true weapon. For the Pirates, the idea that a mechanical fix could restore that edge makes this one of the more important storylines around their ace heading into his next turn. [Read more 🡒]
Mitch Keller Faces A Bigger Pirates Question Than Just Health
Mitch Kellers 2026 season went sideways long before it ended, and the Pirates are still left trying to sort out what comes next for the right-hander. He battled a right arm teres major muscle injury through the year, finished with a 5.29 ERA and was placed on the 60-day injured list Aug. 3, a frustrating turn for a pitcher who had entered the season as one of the most important pieces in Pittsburghs rotation.
Keller did not need surgery, which at least keeps the recovery path relatively straightforward, and he is expected to start throwing again by the end of October. Even so, the bigger question for the Pirates is whether the 30-year-old can put the injury-plagued year behind him and rebound like the frontline arm they invested in when they handed him a five-year, $77 million extension ahead of the 2024 season. [Read more 🡒]