The trade deadline is rapidly approaching, and the rumors are swirling. Every fan hopes their team will add a player who can push them to new heights. We tend to approach the deadline from a team perspective, but what about the players themselves? Many of those dealt in the next few weeks will be free agents after the World Series and want to put their best foot forward before hitting the open market. What is the best situation for them?
Today we’ll look at three starting pitchers who will hit free agency after the season and will likely play for new teams in August. Each player’s situation differs, so the best spot for them to land varies. We’ll start with a hurler who is almost sure to be on a new team a few weeks from now.
Giolito has had a roller coaster of a career thus far. The once highly touted Nationals’ prospect struggled early on and was sent to Chicago in a deal for Adam Eaton as Washington chased a championship. Giolito didn’t thrive initially with the White Sox but turned a corner in 2019, making the All-Star team and finishing sixth in the AL Cy Young voting. He continued to pitch like an ace in 2020 and 2021 and made two postseason starts with mixed results.
Last year, though, the wheels came off for Giolito. He struggled with his control, his K% dropped, and his ERA ballooned to 4.90. This season has been a mixed bag. He looked like his old self early on but struggled in July. Despite his accomplishments, Giolito still needs to prove himself.
The best place for Giolito to land would be with a team with World Series aspirations and talent, preferably in a big market. He needs to contribute to a contender where the lights shine bright and hopefully gets the chance to make multiple postseason starts. Giolito must show that he is still a top-of-the-rotation arm that can perform in any market—not just the offensively-challenged AL Central.
The Yankees, Dodgers, Giants, Rangers, and Diamondbacks are all playoff contenders that may be looking for another starter. However, the Dodgers stand out as the best option for Giolito. Along with perhaps Texas, Los Angeles is best positioned for a deep playoff run and desperately needs another starter. Injuries have ravaged their rotation, and Giolito would immediately step in as a top-three option for the club. As a bonus, Giolito is from Southern California, which may bring him some comfort. If Giolito were to thrive for the Dodgers down the stretch and into the playoffs, it would significantly enhance his appeal when he hits free agency in the Fall.
Unlike Giolito, Montgomery doesn’t need to prove he can pitch under the bright lights, as he spent the first five and a half seasons of his career playing for the Yankees. Since joining the Cardinals last summer, he’s pitched well despite a lack of dominating stuff but hasn’t established himself as a top-of-the-rotation starter. What Montgomery needs to do down the stretch is perform and show the baseball community that he is worthy of a long-term contract. Thus, his best landing spot would be with a club that plays in a pitcher-friendly ballpark, particularly for a lefty.
Of the playoff contenders who may be seeking another starter, the Giants make the most sense for Montgomery. The Dodgers and Yankees also fit the bill; however, the Yankees are more likely to seek a bat, and the Dodgers may prefer a right-hander since their top two starters, Clayton Kershaw and Julio Urías, are lefties. Miami and Milwaukee also make sense if either decides to pursue starting pitching.
Oracle Park has always been pitcher-friendly, and the Giants are known to get the most out of their pitchers. Kevin Gausman, for example, turned his career around in San Francisco. The team’s rotation drops off precipitously after Logan Webb and Alex Cobb; thus, Montgomery would be a welcome addition to the clubhouse. It would be a great environment, situation, and ballpark for him to thrive down the season’s stretch, hopefully ending with some postseason starts.
It’s probably inaccurate to say that the Angels are “likely” to trade Ohtani. However, no 2023 trade deadline article would be complete without discussing the superstar! Unlike Giolito and Montgomery, Ohtani has nothing to prove. Regardless of how he plays during the season’s final months, he’ll be in line for a record-breaking contract this offseason. The only thing that matters for Ohtani this year is winning.
Thus, the best landing spot for the two-way star would be with a club that needs help at both DH and in the rotation and a legit shot at the World Series. Atlanta has the best odds right now, but they have a productive DH already in Marcell Ozuna, and they’ll be the NL favorites without Ohtani. Plus, their farm system isn’t the best right now, and they could ill afford to deplete it.
Ohtani has been heavily linked to the Dodgers, but they’d likely have to move J.D. Martinez if they made a deal, and the Halos aren’t likely to trade him to their in-town rivals. Similarly, as he’s heating up, the Yankees would have to figure out what to do with the highly-paid and very brittle Giancarlo Stanton. Plus, it would still be an uphill climb for the Bombers to come out of the AL this Fall.
Two clubs stand out as the best fit for Ohtani—Tampa Bay and Texas. Both have the prospects to make a deal and would be the favorites to come out of the AL if he joined their roster. The Rangers’ DHs have the fourth-worst OPS in the league this season, and they have a Jacob deGrom-sized hole in their rotation. However, it’s hard to picture the Angels dealing their star to a division rival.
Thus, the Rays make the most sense. Shohei would be a pure rental for Tampa, but that would be the case with nearly every club that acquires him, and the superstar’s presence might push Tampa over the top this year, making it all worth it. At the very least, he’d help boost ticket sales over the season’s final few months, something the Rays notoriously struggle with.
A postseason rotation of Ohtani, Shane McClanahan, Zach Eflin, and Tyler Glasnow would be hard to beat, and Shohei’s bat in the middle of the Rays’ already potent lineup would make them prohibitive favorites to come out of the AL. After five playoff-absent seasons with the Angels, let’s hope we see him in the postseason this year.