Orioles all-in on Skubal? Who lands White Sox stars? 5 burning trade deadline questions

Count the Orioles and Padres are among the many contenders in need of frontline starters. The Yankees have several holes to fill. The overachieving Red Sox still might be deciding whether to buy or sell. 

Results from this weekend, which includes three games on the FOX Saturday Baseball lineup — Baltimore hosts San Diego (4:05 p.m. ET on FS1), the Red Sox host the Yankees (7:15 p.m. ET on FOX) and the White Sox host the Mariners (7:15 p.m. ET on FOX — will likely determine what course of action several clubs take ahead of Tuesday’s trade deadline.

Accordingly, FOX Sports MLB experts Deesha Thosar and Rowan Kavner tackle these topics and more in this week’s roundtable.

1. Should the Orioles make the Tigers an offer for Tarik Skubal that they can’t refuse or look to acquire one of Garrett Crochet, Nathan Eovaldi, Erick Fedde, Zach Eflin or Jack Flaherty (again)?

Kavner: If any team is equipped to get Skubal, it’s the Orioles. He is, without question, the best pitcher who could be available for the right price. And if I’m Baltimore, I go all-in to make it happen (although I’m not anticipating this actually happening). The reality is that at some point the Orioles will have to move some of their top prospects. They need starting pitching help now. They’ll need it next year, too, particularly if Corbin Burnes goes elsewhere in free agency. What better time than now to add a potential Cy Young Award winner under team control for another two years?

Thosar: I don’t think it makes sense for the Tigers to trade their first franchise ace since Justin Verlander, so I continue to believe they won’t do it. Nathan Eovaldi, though, seems like the perfect fit for the O’s. He can complement Corbin Burnes and really solidify a strong 1-2 punch for the playoffs, where pitching matters more than at any point in the season. 

Eovaldi is excellent in the playoffs, posting a 3.05 ERA in 17 starts and coming off a strong performance for the championship Rangers last year. His track record is exactly the kind of spark the O’s need to put an exclamation point on their expected dominance in October. Despite the expectation they would go far, the lack of strong, proven starting pitching is a large part of the reason they crumbled in the playoffs last year. The O’s can quickly learn from their mistake and load up on arms to be battle-ready until November.

2. How aggressive should the Padres be to add starting pitching at the deadline?

Thosar: Aggressive. Since the Padres have the fourth-best farm system in baseball, according to MLB Pipeline, they have the prospect capital to really go for a top-end starter at the deadline. We’ve been waiting for this roster to consistently play to its potential since Xander Bogaerts, Fernando Tatís Jr. and Manny Machado started playing together. 

Perhaps now, with better starting pitching and an offense that might just come together, the Padres will have a shot at going at least as deep into the postseason as they did in 2022, when they lost to the Phillies in the NLCS. Another top-end starter alongside Dylan Cease and the soon-to-be-returning Joe Musgrove could be the difference between fizzling out in late September and a longer, scarier stretch into October.

Kavner: They definitely should add a starter. Michael King and Matt Waldron have already set career highs in innings, and by the time they have to make the decision, they won’t know exactly when Joe Musgrove or Yu Darvish will be back. After already acquiring Dylan Cease and Luis Arráez, the prudent thing would probably be to look for a mid-rotation arm, but I would never rule out AJ Preller from doing something a little more stunning.

3. The Yankees appear to be a pretty incomplete team despite having the second-most wins in the American League. What do you expect them to do before the deadline?

Kavner: They can’t patch all of the holes, but I would expect them to add an infielder and a reliever, at the least. They rank in the bottom 10 in fWAR at first base, second base and third base, so a versatile infielder such as Luis Rengifo or a corner infielder such as Isaac Paredes or really anyone who can serve as another offensive threat beyond Aaron Judge and Juan Soto (and Giancarlo Stanton, when healthy) seems like a necessity. Finding a reliever should be an easier endeavor. They need to add someone capable of missing bats, particularly against righties.

Thosar: All eyes will be on Brian Cashman, who is perhaps facing the most pressure he has ever faced in his 26-year run as Yankees GM, ahead of this trade deadline. He has so many holes to fix on the roster that it will be fascinating to see where he starts, and how much he can actually address through trades. The Yankees first and foremost need a serviceable third baseman, and at this point, any bat over DJ LeMahieu and Oswaldo Cabrera will be an upgrade. They also need bullpen help, so I’m expecting Cashman to pick up a reliever, or two. Another starter wouldn’t hurt either, but the rotation is by no means the main problem right now. 

The Yankees need everyone not named Aaron Judge and Juan Soto to start hitting like major-leaguers, but their isn’t another elite hitter among that group. With all of these roster problems, and sky-high pressure to go to the World Series with Soto, the Yankees have to get creative and be aggressive at this year’s deadline.

4. How serious of a buyer should the Red Sox be? Should they trade Kenley Jansen?

Thosar: The Red Sox’s path to the postseason is less crowded now that there are fewer teams in their way, and the Yankees have been exposed by Boston, too. It’s a group that should feel confident following an extended stretch of success (their past week notwithstanding). A boost by the front office in the form of solid additions, without having to give too much up, should only help add to their assurance. 

Chief baseball officer Craig Breslow can reward the club for playing hard and being within one game of a wild-card spot — despite a roster that didn’t look set up for success at the beginning of the year — by making a defining mark on the immediate future of this organization. Through wild-card contention that could very well result in a deep run, the Red Sox might shock us and go back to being, well, the Red Sox again.

Kavner: They didn’t go “full throttle” the way Red Sox fans hoped they would this winter. Now’s the chance to remedy that inaction. They haven’t gone to the playoffs in three years. They haven’t won the division since winning the World Series in 2018. They should at least try while they’re in striking distance. Now, that doesn’t mean they need to be dealing away top prospects Marcelo Mayer, Roman Anthony or Kyle Teel, but they’ve demonstrated enough that they should at least be light buyers and should be in the market for a middle infielder, a starter and a reliever. A buyer-to-buyer mutually beneficial deal where the Red Sox trade Jansen for another helpful piece might have made more sense a month ago, but I don’t think the bullpen is in a place right now where they can afford to do that.

5. What’s your best guess for whom the White Sox’s Garrett Crochet and Luis Robert will be playing for next week?

Kavner: Given what it would take to get them, the uncertainty around Crochet’s workload and reported unwillingness to pitch in October without an extension and Robert’s health concerns and dip in production this year, I’m starting to wonder if Chicago just holds on to both of them and shops them again in the winter. So, if I had to guess, I’d say they stay put. If they did get moved somewhere, I’d say the Dodgers in a package deal. I maintain that I think the Phillies should go all-in for Robert, but the Dodgers might feel more pressure to win now after their back-to-back first-round exits and their commitment to Shohei Ohtani.

Thosar: Similar to how we all guessed throughout the offseason that Shohei Ohtani would sign with the Dodgers, Crochet’s name has been linked to Los Angeles for so long now that I would surprised if he didn’t end up there. It’s possible, and this is just speculation, that the Dodgers have been convinced they have the right package to land Crochet and Robert for a while now, and the White Sox are using that leverage to field other offers from rival executives. 

All we’ve heard is that the Dodgers are looking to add a starter and an impact bat, and Crochet and Robert perfectly fit that bill. There are concerns surrounding each of them, particularly with Crochet’s possible innings limit and Robert’s streakiness mixed with his injury history. But Crochet is still the most valuable starter on the market thanks in part to his remaining two years of team control, so this would be a major splash for any team that lands him — my best guess being the superteam Dodgers.

Bonus: How much do you attribute Seattle’s offensive struggles to T-Mobile Park and do you think the club needs to alter its dimensions again?

Thosar: According to Statcast, T-Mobile Park is the most difficult park to hit in across all of MLB, and it’s not particularly close. That’s been the case since 2020. It would make sense that Seattle’s offense performs slightly better on the road than it does at home due to their dimensions, so it’s worth it to alter them and make hitting less difficult for themselves, at the very least.

Kavner: It’s got to be part of it, especially when considering how precipitously the free agents who go there tend to crater (see: Jorge Polanco, Mitch Garver). Earlier this year, I asked Teoscar Hernández about it, and he didn’t have a clear answer. He said it’s a great place to play and he loved the support from the fans and the city, but he believed the environment tends to suppress offense: “I hit the ball the same way I hit the ball everywhere, but hitting the ball there, it just dies,” he said. 

The marine layer, cool weather and the mental block of playing there all year probably all play a role. Of course, the flip side of that is all those same factors benefit their elite pitching staff. For now, I’d like to see the Mariners pay for better offensive players first before I worry about the park’s dimensions.

Deesha Thosar is an MLB writer for FOX Sports. She previously covered the Mets as a beat reporter for the New York Daily News. The daughter of Indian immigrants, Deesha grew up on Long Island and now lives in Queens. Follow her on Twitter at @DeeshaThosar.

Rowan Kavner is an MLB writer for FOX Sports. He previously covered the L.A. Dodgers, LA Clippers and Dallas Cowboys. An LSU grad, Rowan was born in California, grew up in Texas, then moved back to the West Coast in 2014. Follow him on Twitter at @RowanKavner.

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