10 Biggest Questions Following A Frenzied, Drama-Filled MLB Trade Deadline

Now that the chaotic frenzy of MLB’s trade-deadline day is over, we have a better idea of where some contenders stand. 

The Dodgers landed Tarik Skubal, stole the deadline and sparked fresh debate about baseball’s impending labor negotiations. Fringe clubs like the Mariners, Guardians, Padres and Pirates decided to buy and make their push for the postseason. Teams that we expected to be more ambitious — like the Yankees, Braves and Brewers — ultimately disappointed. 

But we’ve still got some questions. Here are 10 that we’re curious about as we enter baseball’s stretch run. 

While it’s true that adding a two-time Cy Young award winner to an already stacked rotation gives the reigning back-to-back champions a ceiling that no other team can match, Skubal’s addition doesn’t guarantee a Dodgers three-peat. 

Health and matchups still decide what happens in October, and we saw the Dodgers get pushed to the brink by a red-hot Blue Jays team just last year. The rest of the league is motivated to dethrone the Dodgers, and this might all come down to who gets hot at the right time. Skubal and the Dodgers, while staggeringly dominant, are not indestructible. 

Boston surrendered the deadline’s biggest prospect haul, dealing Carlos Narvaez and top prospects Anthony Eyanson, Kyson Witherspoon, Enddy Azocar and a player to be named later or cash considerations for Orioles catcher Adley Rutschman. 

The three-time All-Star has been sidelined with a wrist injury since July 20, his fifth stint on the injured list in a 14-man span. It’s not great that the Red Sox seem to have no idea when Rutschman will make his debut, and he’ll hit free agency after next season, creating an even shorter window for Boston’s return on its investment. 

The Red Sox paid a steep price, to be sure, but Rutschman addresses their roster flaw, and you have to appreciate Boston going all-in — even if this might end up not working out for the club long term.

The departure of Rutschman reminds me of the impactful loss of Pete Alonso in Queens, and how letting the Polar Bear walk to Baltimore still and might forever distress the Mets’ fan base. 

It’s hard for the Orioles to say no to the massive package the Red Sox pushed across the table. After all, Rutschman’s Baltimore tenure did not even feature a single playoff win. But you have to feel sorry for O’s fans, who are dealing with major heartbreak after the blockbuster in-division trade. 

The Phillies have one of the worst offenses in baseball, with their 92 wRC+ tied with the Mets and Rockies for 26th in the majors. Three-time batting champion Luis Arraez is a fantastic who should help improve their offensive numbers. But I still would’ve liked to see Philly add more, particularly a right-handed-hitting outfielder.

The club’s recent October failures have come down to situational execution, and second baseman Arraez’s addition will require a defensive realignment, with Bryce Harper, Bryson Stott and Alec Bohm moving positions. That will present more challenges to a Phillies team with the worst Defensive Runs Saved (-47) in MLB. 

All eyes will be on the dozen starting pitchers who found new homes on deadline day, including Kevin Gausman and Clay Holmes to the Cubs, Robbie Ray and Casey Mize to the Padres, Freddy Peralta to the Rays, José Soriano to the Blue Jays, Foster Griffin to the Guardians, Luis Castillo to the White Sox, Dustin May to the Brewers, Tyler Mahle to the Braves, and of course Skubal to the Dodgers. 

This one will be answered by the end of September, but the Cubs might experience the biggest benefit here. 

New Cub Kevin Gausman has a 3.83 ERA in 14 career postseason games. (Photo by Joe Robbins/Icon Sportswire via Getty Images)

The Yankees, Braves and Brewers were all considered losers this deadline after failing to meet their needs and add in the significant ways that they were expected to. New York didn’t get any bullpen or catching help. Atlanta didn’t make a splash on the starting-pitching market even though it was flooded with solid options. And Milwaukee refused to part with top prospects in their loaded system. 

The Yankees face the most pressure to win a championship, and they should be the most nervous about neglecting their checklist.

It’s not Skubal. The Dodgers, better than anyone, can afford to ease him in without sacrificing their winning ways.

So the answer here has to be Arraez in Philly, Luis Garcia Jr. and Heliot Ramos in the Bronx, and Peralta in Tampa Bay. A lot is hinging on Garcia and Ramos being the answer to New York’s offensive problems, but at least they’re under team control beyond 2026. 

Arraez and Peralta are free agents after this year, plus they carry huge stakes for the success of their new clubs.

Mets outfielder Luis Robert Jr. and, given the news from the Bronx today, Yankees shortstop Anthony Volpe. Both of these bats don’t have a ton of value right now, and the Mets tried hard to trade Robert, to no avail, likely because rival executives balked at the $20 million he’s owed next year. 

Volpe was demoted to Triple-A hours after the deadline, and with Yankees No. 1 prospect George Lombard Jr. called up to replace him at shortstop, it’s hard to see how Volpe fits into their long-term plans. And, with so few shortstops available, New York probably could’ve addressed their bullpen or catching needs by moving him. 

The AL East is going to be popcorn-worthy from now until the final day of the regular season. 

The Red Sox, of course, were the most aggressive of the divisional contenders, and they’ve been playing really well as of late. The Rays whiffed on Skubal but still bolstered their rotation with Peralta, and they’ve been the team to beat all season. The Yankees stayed relatively quiet and passed on major upgrades, which could end up hurting them. 

New York is in second place, 3.5 games behind the Rays. Boston is in third place, 5.5 games behind Tampa. It will be fascinating to see how much that race changes over the next two months. 

Freddy Peralta talks to the media after being acquired by the first-place Rays for the stretch run. (Photo by Ray Bahner/MLB Photos via Getty Images)

Without doing a full-on deep dive that can be reserved for the offseason, when front offices will again try to use some of the prospects they just gained as leverage in trade deals, it seems like the Blue Jays and Cubs took the biggest hits. 

Toronto parted ways with its top prospect, shortstop Arjun Nimmala, in order to gain a controllable arm in José Soriano, which addressed one of the team’s biggest current needs. And the Cubs dealt their No. 2 overall prospect, infielder Jefferson Rojas, to the Mets in order to get Holmes. 

These were big blows to their farm systems, even though it might help them in the short term.