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New York Yankees fans love to criticize Hal Steinbrenner and Brian Cashman for not spending more and doing more to help their team win. The Yankees haven't won the World Series since 2009, which feels like a lifetime for some of their supporters.
However, things could be much worse. Just ask Pittsburgh Pirates fans.
The Pirates haven't won a World Series since 1979, nor have they come particularly close. They've been largely inept over the last 45 years, making just six playoff appearances during that time.
The last decade has been especially rough for Pittsburgh. The franchise has endured nine straight losing season since its last postseason appearance in 2015, and seems well on its way to another moribund campaign after starting the year 3-7.
New York, on the other hand, hasn't had a losing season since 1992 and makes the playoffs almost every year.
While the Yankees are always near the top of the league in payroll, the Pirates usually rank near the bottom. According to Spotrac, New York has the third-highest payroll in baseball at $289 million — over $200 higher than Pittsburgh's $88 million figure (26th in MLB).
The Pirates have kept their payroll low by limiting their free-agent spending, which Yankees TV broadcaster Michael Kay called out on air during Sunday's game.
Yankees broadcaster Michael Kay talks about the state of the Pirates and the potential they could have but don’t have. Take a watch. pic.twitter.com/aLIKhG7LsB
— Greg Finley (@_GregFinley) April 6, 2025
Kay noted that Pittsburgh only signed one-year deals in free agency last winter, which has been the organization's strategy for years. According to Kay's research, the Pirates haven't signed a free agent to a multi-year deal since December 2016, when they inked former starting pitcher Ivan Nova to a modest three-year, $26 million contract.
While Pittsburgh's lack of spending could be justified during its recent rebuild, that's no longer the case. The franchise has a generational talent in Paul Skenes, but still failed to build a competitive team around him last winter.
If owner Bob Nutting doesn't start investing more in the roster and allow general manager Ben Cherington to spend more aggressively, the Pirates risk squandering Skenes' prime, similar to how the Los Angeles Angels wasted some of the best years of Mike Trout and Shohei Ohtani's careers.
Skenes is arguably the best pitcher in baseball, but he only plays every fifth day. Pittsburgh needs to give him a strong supporting cast if it wants to be a playoff contender.
The Pirates have a beautiful ballpark, a passionate fanbase and a bona fide ace. Now they just need an owner who cares.
More must-reads:
- Has Cal Raleigh overtaken Aaron Judge in MVP race amid Yankee slugger's slump?
- Red Sox top prospect to undergo season-ending wrist surgery
- The 'Most multi-HR games by MLB team' quiz
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Former Braves Ace Seeing All-Star Season with Yankees Crumble
The early months of the 2025 season saw former Atlanta Braves ace Max Fried deliver one of his best runs of success on the mound. Through 11 starts, he had a 1.29 ERA. He was giving his new team, the New York Yankees, plenty of innings, nearly seven per start. Giving him his third All-Star appearance was a no-brainer, and he was a frontrunner for the American League Cy Young Award. Over the month of June, he came down to earth a bit. By that, we mean he was allowing a couple runs per start instead of one or fewer. His ERA was still 1.91 on July. Then, the wheels flew off the tracks. He hasn't allowed fewer than three earned runs since. He hasn't given up fewer than four runs in a start where he pitched more than five innings, and he only made it through five in one of those starts in which he allowed just three runs. On Saturday, he allowed a season-high seven earned runs when the Yankees took on the St. Louis Cardinals. In his last eight starts, his ERA is 6.80, and his season ERA is now up to 3.26. That's a tick higher than last season (3.25) over 29 starts. All hopes of taking home a Cy Young have gone out the window. At this point, the only hope he and the Yankees have is if he can catch his breath and get back to form. If they're lucky, it's just a bad stretch. July and August weren't so great for Fried either. Granted, last season, Fried was coming off missing time due to forearm neuritis. This year, his injury was a blister. Outside of the All-Star Break, he hasn't gotten more than his usual rest time between starts. Maybe it's a genuine rough patch, and he just needs to make the proper adjustments in order to figure it out. Time will tell. Fried signed with the Yankees (eight years, $218 million) over the offseason after eight seasons with the Braves. In Atlanta, he made two All-Star Games, won two Gold Gloves and was part of the 2021 World Series-winning team. He notably pitched the decisive Game 6. The Braves haven't exactly found the pitcher who will take his place, but based on how things are going, he would simply be joining the woes already plaguing the team over the last few months. More From Atlanta Braves on SI
Cowboys' Tyler Booker Reacts To 'Dream Come True' Debut
Dallas Cowboys first-round pick Tyler Booker finally had his NFL debut in the second preseason game, in the 31-13 loss to the Baltimore Ravens. And yeah, he was as advertised. Booker looked at home in the NFL, and yes, we get it, it's preseason, but we saw all that we needed to, and given the fact that Dallas had its best running plays behind the right side of the offensive line, ittells you all you need to know. But how was getting on the grass in a real NFL game? “Great,” Booker said. "It's really a dream come true. I was glad to be out there with my teammates. Glad to see some live action, and I'm very excited to watch the film. Just going out there having any debut was really a dream come true. Being able to play with my teammates and some live action. It was definitely a great time. Had a great time. Perhaps the best thing was that Booker wasn't just able to be serviceable, he was good. Per PFF, Booker, on 15 pass plays, didn't offer up a single pressure with No. 52 stout against the Ravens pass rush, and also, his push in the run game was something that will no doubt make Schottenheimer and the coaching staff happy. Yes, it was only preseason, but with all the question marks surrounding the Cowboys, one that we don't have is whether Booker will be able to compete at a high level and look good doing it.
Vikings GM Kwesi Adofo-Mensah's biggest find is ready to take a huge step forward, and it could be huge for Brian Flores' defense
After joint practice on Wednesday between the Minnesota Vikings and New England Patriots, I was asked by some members of the Patriots beat about just one player. "Who's 61? He's a dude." That player is Jalen Redmond, who has quite the story heading into his second season with the Vikings. He was playing in the UFL in the spring of 2024 with the Arlington Renegades. He was a signing the Vikings made on June 18th, 2024, which came after mandatory minicamp. Redmond was the 90th player on the roster and excelled throughout training camp to earn a roster spot. That ability is showing up once again. Jalen Redmond is taking another step forward The signing of Redmond was a massive win for general manager Kwesi Adofo-Mensah and his scouting staff, especially Ryan Grigson, who was given a lot of credit for finding him. "I remember he [Grigson] called me and said, 'I like this guy.' I think it was late May," Adofo-Mensah explained. "You have to ask yourself, what's your standard for bringing people in, because a lot of good players are on teams already, so there's going to be something there that's not perfect, not clean, and earlier he had injuries, so you've got to understand why he's available, but ultimately here's why he might be a good bet. "And you saw the flashes for an interior guy with burst, his run defense kind of jumped out to me. That's the other thing, when you've been together for two or three years, and my history with Grigson before, he knows how to communicate with me, makes a cut-up, knows exactly what we look for." You can see the power and explosiveness in Redmond's game. He rarely gets washed out by the offensive line, and often penetrates the backfield with his ability. Where things have gotten really interesting with Redmons is seeing how good he can be from a short and long-term perspective. Last season, Redmond played in 13 games and flashed in a major way. While he went undrafted out of Oklahoma, it wasn't so much due to talent, but a health issue that kept him from being selected. He certainly looks like a player who should have been selected. Over the course of the season, Redmond got one sack and 6.0 tackles for loss to pair with 18 tackles. His ability to be a penetrating force on the line earned him a starting role at the end of the season, with two starts in his first year with the Vikings. Going into year two, Redmond shouldn't be overlooked. He won't be a starter with the additions of Jonathan Allen and Javon Hargrave, but it shouldn't be much of a surprise if he approaches 500 snaps as a rotational player. His teammates believe he's a stud, something that Jonathan Greenard emphasized last week. "Redmond is a dog," said Greenard after Redmond's great practice on Thursday. "Jalen's been a dog since last year in training camp. I knew he was a dog when he got thrown out of practices last year. So I was like, listen, from that day forward, he got thrown out, he came back in just completely, just dominating. And at that point even to see it during the season and see him continuously build. Now I'm like, man, everybody knows, but when you see, obviously, you bring in two guys like JA [Jonathan Allen] and Grave [Javon Hargrave], you kind of think that he gets put in the wayside, making the same place he was last year, if not more. And that just helps us out to know that it's not gonna drop off whenever those guys get a breather or something like that. If I'm coaching, I'm putting him in." Don't sleep on Redmond going into this season, as he's only getting better.
Pittsburgh Steelers Could Be Forced To Lean On 4th Round Rookie Due To Injuries
The Pittsburgh Steelers’ depth at outside linebacker is being tested early this preseason. With Alex Highsmith nursing a lingering groin injury and backup Nick Herbig also sidelined with a soft tissue issue, rookie Jack Sawyer may need to step up quicker than anticipated. The fourth-round pick out of Ohio State has displayed flashes of potential but also revealed areas for growth as he navigates the leap to the NFL. Pittsburgh Steelers Jack Sawyer: Getting An Opportunity Highsmith’s groin injury has understandably raised concerns within the Pittsburgh Steelers organization. Head coach Mike Tomlin has been cautious in assigning timelines, but soft tissue injuries are notoriously tricky, with recovery that can vary from days to weeks. While Highsmith remains a critical component of Pittsburgh’s pass rush, his absence, coupled with Herbig’s injury, leaves the Steelers thin at a crucial position. Enter Jack Sawyer, who now faces an opportunity to carve out meaningful reps during the preseason and, potentially, the regular season. Sawyer has all the physical tools that made him a fan favorite during the 2025 NFL Draft. His 6-foot-5, 260-pound frame and relentless motor have coaches intrigued about his ceiling. However, as with most rookies, the transition from college to professional football has not been without challenges. Preseason Performance Shows Promise and Growing Pains Sawyer’s preseason tape has been a mixed bag so far. NFL Draft analyst Jon Ledyard captured this sentiment perfectly, tweeting after the Steelers’ 17-14 loss to the Tampa Bay Buccaneers, “The difference between Herbig off the ball and Sawyer off the ball is like watching a different sport. Steelers better pray Herbig and Highsmith are good to go Week 1.” While this critique highlights Sawyer’s struggles with recognition and disengaging from blocks, it’s important to keep in mind that he’s still adapting to the complexities of an NFL defense. Sawyer recorded just one tackle against the Buccaneers, but stats don’t tell the whole story. Even in limited action, he showed glimpses of his potential. His strength and motor allowed him to pressure the pocket at times, even if the consistency wasn’t always there. The rookie’s effort on every snap is evident, and his ability to improve will rely on sharpening his technique and decision-making in the weeks ahead. Challenges Transitioning to the NFL One of Sawyer’s biggest hurdles has been adjusting to the speed and complexity of NFL offenses. At Ohio State, his sheer athleticism often allowed him to overpower opponents, but in the NFL, offensive tackles are more skilled and quicker to neutralize a pass rush. Another area that needs improvement is his ability to diagnose run plays and shed blocks effectively. This deficiency was apparent against the Buccaneers, where he appeared a step behind in run defense on multiple occasions. These are teachable moments, however, and with guidance from the coaching staff, Sawyer has the tools to address these gaps. Despite the growing pains, Sawyer’s raw talent and versatility make him a key player to watch. Pittsburgh’s defensive scheme places significant emphasis on outside linebacker depth to maintain relentless pressure on quarterbacks. With Highsmith and Herbig sidelined, Sawyer could see invaluable snaps to accelerate his development. The Opportunity Ahead This next stretch of preseason games represents a pivotal time for Sawyer. With both injuries and roster evaluation in play, he stands to benefit from increased exposure against NFL-caliber competition. The Steelers have a proven track record of developing edge rushers under Tomlin’s tenure, and Sawyer has a chance to tap into that system if he can capitalize on his opportunities. Sawyer’s ability to adapt quickly and improve on specific aspects of his game will determine whether he can build the trust of the coaching staff. His physical traits—size, strength, and an innate drive to compete—aren’t in question, but his ability to execute consistently at the pro level needs refinement. Final Thoughts Jack Sawyer’s NFL career is in its infancy, but the potential is evident, even if the results haven’t fully materialized just yet. Injuries to key players like Alex Highsmith may force the Steelers to lean on Sawyer sooner than expected. While the rookie’s preseason performances have been uneven, this is the kind of trial by fire that can fast-track development. Whether Sawyer can rise to the occasion and make the most of this opportunity remains to be seen. What’s clear is that Pittsburgh is banking on its next man up, and Sawyer has all the tools to deliver if he can put it together.
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