LAS VEGAS — The Pittsburgh Pirates have struggled for such a long time that they've been one of the poster teams for losing in MLB.

One of the biggest reasons for the Pirates struggling for so long is that they are a small-market team and can't acquire the best talent that the bigger teams do, falling near or at the bottom of payrolls in baseball.

The Pirates and other small-market teams are gearing up for an impending lockout and the owners have hopes of instituting a salary cap and floor, which would go into effect by the 2028 season, that they believe will level the playing field among all 30 teams.

A salary cap is something that the players' union (MLBPA) is against, and a super agent like Scott Boras backs them up in that regard and gives no excuses for teams that can't win.

Boras Sees Way for Small Market Teams to Win

The 2026 season was different than most, as the World Series featured both small-market teams, with the Milwaukee Brewers defeating the Tampa Bay Rays in five games.

Both teams had two of the lower payrolls in baseball, with the Brewers at 19th and the Rays at 28th, the third-lowest.

This World Series went against the narrative that only big-market teams can win and Boras sees it as one that shows there are different ways to win in baseball.

He specifically looked at the Brewers, who have dominated in the draft with their pitching, particularly ace Jacob Misiorowski, and the culture that National League Manager of the Year Pat Murphy established as reasons for their success and how others can do the same.

“Competitiveness is not necessarily, there’s the intellect involved. That’s the freedom of having a system that allows you to portray your levels of success, your reasons for success, your equations for success...

"These are the things that fans enjoy that everyone enjoys. The mystery of the game was so complete where we have a diverse approach to championship play. Nothing has been more evidenced than what has occurred two years before and what occurred this year and the evidence is clear because you know what, we have ownership, we have an intellectual structure of executives that have all created something that beats what was unbeatable the prior year.

"So all of those allow you to focus on what they’re doing. What can I do to counter it, and yet I have the means to do it, regardless of an approach where I use the draft? No, I use free agency. I’m required to win every year, or no, I’m not. Those markets have varying standards that they apply there.”

Boras Doesn't See Cap Helping Small Market Teams Win

While fans and owners of small-market teams may say they can't win without the cap and floor, which are prevalent in the other major sports leagues in the United States, Boras doesn't agree.

He thinks teams need to get more creative in how they can become winners, whether that be by finding new ways of adding capital and money, looking at other team models and doing whatever they can to win.

“I think my point of it is in the business community, you have an obligation to your fans to compete," Boras said. "So if everybody else in your division or everybody else in the league is utilizing private equity and capital to grow their team, and you say, “I’m not doing that. I choose not to do that.” 

“Then I think the fans will respond in a way that’s saying, “Why don’t you do what [San Diego Padres owner] Peter Seidler did? Why don’t you do what the Brewers did? Why don’t you create an inventive course of conduct that allows you to compete?” 

“Because that’s what they’re doing with less spending, or they’re doing with more spending or they’re doing by bringing in new owners.

“All of those resources are available to how I’m going to treat my fanbase, my franchise and then I think it’s up to those that surround the team to understand. What is best in choice, where we’re hoping to have an ownership structure that allows for us to be what others are.

"So this idea that smaller markets don’t win, something tells me, I think it’s been proven that’s not accurate.”

Boras also thinks that great players are always going to be compensated well and that finding great players is one of the toughest parts about building a winning ball club.

He wants teams to find those ways of winning that are outside of just spending money, which some small market teams like the Padres, Brewers and Rays have shown in recent years.

 “...The idea of it is, look, we have models; we have environments like that have been successful.

“The idea of what ownership does and what they choose to do is that they have to understand how they operate, why they operate and obviously if I’m going to operate like I did 20 years ago and everybody in my division is operating differently, I’m not going to be able to capitalize the franchise to a level that others have and create an opportunity because, remember, talent is coveted, rights are coveted," Boras said. 

There are few players that are great players. So consequently, clubs understand they have to pursue great players to achieve their goal of greatness and that understanding has to eternally be adopted so that they can preempt it or they can advance it and create a theory of their own and we have many examples...”

 “The idea of it is, look, we have models, we have environments like that have been successful. Our system allows you to be creative and successful. It allows you to think internally, externally; it allows you to bring people in, bring capital in; it allows you to do a lot of things. That equation is their own.” 

Is Boras Right About Pirates and Small Market Teams?

Boras is always going to side with the players and support them doing what they can to increase their value, salary and compensation, as any good agent would do.

He does make good points for small market teams having success and that there are ways for them to do so without a cap/floor that MLB is proposing in the next CBA.

It's still a big gap between teams that win the World Series and those that don't, as the Brewers were the first small-market ball club to win it all since the Kansas City Royals in 2015.

The Brewers also won their first World Series in their existence and won the pennant for the first time since 1982, 44 years prior.

Teams like the Rays, Padres and Cleveland Guardians have worked hard to establish winning cultures, but have fallen short of the ultimate goal.

It's also hard for fans to see teams like the Los Angeles Dodgers, New York Yankees and other big market franchises sign players for record fees, while their team comes nowhere close.

The best teams spend money, and big markets/heavy spenders are almost always coming out on top in every season.

There's no doubt the Pirates have to improve throughout the franchise, as payroll can't be the only excuse for their futility for the past few decades.

But the Pirates also have some top talent on their roster, which could lead them to great success, but is also nearing free agency.

Expecting the Pirates to re-sign the likes of ace Paul Skenes and burgeoning star Oneil Cruz to contract extensions is extremely unlikely, which isn't the case for big market teams.

Regardless of whether the salary cap/floor is implemented, revenue sharing needs to be increased, which both the owners and MLBPA have proposed for the new CBA, but in different ways.

Doing so will not only allow teams to keep their talent, but it will reward that talent with fair compensation for their success.