Free agency decisions and trades typically headline the MLB offseason, but managerial decisions also make their way to the forefront of the franchise’s minds. They don’t throw the pitches or stand in the batter’s box, but they are entrusted with leading the locker room. Let’s take a look at which five managers have something to prove during the final month and change of the 2024 season.

Aaron Boone, New York Yankees

Being a manager is hard enough, but managing the New York Yankees brings another level of challenges and expectations of their own. In fairness, Boone has had a winning season in all seven years he has been leading the Yankees, accumulating 586 wins versus 415 losses overall. He’s made the playoffs in all but one of them (2023), but he had Aaron Judge for only 106 games. Sounds like a track record of success, right?
Well, absolutely. But regular season success doesn’t correlate with postseason success, and that is reflected in his 14-17 postseason record. Since Boone has been with the Yankees, he’s lost in the ALCS twice, ALDS twice, and the Wild Card game once, not getting to the World Series one time. For a franchise with 27 championships and currently on a 14 (going on 15) year World Series drought, trips to the ALCS and ALDS won’t cut it.
In recent seasons, Boone’s teams have had a tendency to flame out after fantastic starts. Take 2022, for example, when the Yankees were 38 games over .500 on July 8th, but went 38-40 the rest of the way and watched the Houston Astros take the top seed in the American League. Even this season, the Yankees were 28 games over .500 on June 14th, but since then, they’ve posted a 27-32 mark. Of course, both of the examples I provided haven’t hindered the Yankees from making the postseason, and there is such a thing as regressing to the mean. Furthermore, Boone has also had to deal with a plethora of injuries throughout his tenure in the Bronx, resulting in several roster moves that handcuffed the team to some degree.
There’s been no shortage of talent walking through the doors of Yankee Stadium; Aaron Judge is on pace for his second 60-home run season, Juan Soto is playing at an MVP level, Gerrit Cole just won a Cy Young, and Boone did start managing this team with Giancarlo Stanton in his prime years. You can’t punish Boone for winning, but when does the front office get tired of ALCS exits?

Dave Roberts – Los Angeles Dodgers

Speaking of “no shortage of talent,” I present to you Dave Roberts. Unlike Boone, Roberts has a World Series title to his name when he won the 2020 crown during the COVID-shortened season. Whether you want to call it “Mickey Mouse” or not, they were still playing baseball.
A career 831-496 record and seven division titles may make Roberts being on this quite comical, but there’s a reason he’s here. They took a team that won 100 games last season and added the best player in baseball – Shohei Ohtani – as well as standout free-agent pitcher Yoshinobu Yamamoto. Add that to a roster already with Mookie Betts, Freddie Freeman, and All-Star Teoscar Hernandez, and this team should be a World Series favourite.
The problem is that this team has been one of the World Series favourites year after year after year…after year, including last year when they were swept in the ALDS by the Arizona Diamondbacks. Roberts has been handed a roster that would make a Wells Fargo or PNC say, “Is there enough money to pay these guys?” Like Boone, you can’t be upset with the regular season success, but the talent he has had has warranted more than one World Series. Another quick NLDS exit will outrage the fan base.

Joe Espada – Houston Astros

It almost feels wrong to include a first-year manager in this, but Espada has been in the Astros organization since the 2018 season. Safe to say, he’s been around a winning environment for quite some time.
Despite the near-decade-long stretch of dominance, it’s been an abnormal year for the Astros. They were swept by the Yankees to start the season, making Espada’s first win as a manager Ronel Bianco’s no-hitter against the Blue Jays. They were in third place in the AL West from May 15th through June 16th, second place from June 18th through July 14th, and they’ve been swapping first and second place with the Mariners since July 19th. In short, they extinguished Seattle’s 10-game division lead in just under two months.
They’re currently 70-60, they’ve fought a multitude of substantial pitching injuries and just held their own with the Baltimore Orioles over a four-game series. This isn’t the most dangerous Astros team ever assembled, but it’s still one that can make a World Series run, especially as they get relatively healthier. Nobody is really establishing themselves as frontrunners in the American League, so why not the Astros?
Like I mentioned earlier, this isn’t Espada’s first rodeo with the Astros and October. That’s where I believe he’s got something to prove. AJ Hinch and Dusty Baker started it. It’s Espada’s turn.

Mike Shildt – San Diego Padres

The pressure may be on Padres GM AJ Preller as well, as baseball media has questioned whether or not he should be on the hot seat. Shildt isn’t on the hot seat (at least that I know of), but he’s got something to prove this year.
The Padres have joined the Diamondbacks in the push to dethrone the Dodgers in the AL West. In Shildt’s first season with the Padres, San Diego currently sits at 74-58, just 4.5 games back of Los Angeles for the division lead, and they’ve been in second place for the majority of the season. He spent four seasons with the St. Louis Cardinals from 2018 to 2021, but he posted a less-than-impressive 4-9 playoff record during his time there.
They have some guys to get back from injury, but Shildt arguably has more of a talented roster with San Diego than he did any year in St. Louis. Jackson Merrill has a legitimate Rookie of the Year case, Jurickson Profar is having a career season, and Michael King has found his footing after a tough start to the year, just to name a few things going in San Diego’s favour. Furthermore, Preller bolstered San Diego’s bullpen at this year’s trade deadline, acquiring Tanner Scott and Jason Adam.
The Padres are flying under the radar and could make a 2022-like run in the playoffs. Shildt has an opportunity to rewrite his playoff history with this team.

Dave Martinez – Washington Nationals

Since winning the World Series in 2019, Martinez has managed through a rebuild. Four straight last-place finishes in the NL East, one season with over 100 losses, and several franchise superstars being dealt away at trade deadlines – that about sums it up. But, now, fans are starting to see all of those acquired pieces reach the big leagues, and the Nationals are arguably a few players away from turning into contenders.
C.J. Abrams (18 HRs/60 RBIs) made his first career All-Star game, Jake Irvin (3.80 ERA) has taken a step forward, and James Wood (.830 OPS) has brought a lot of excitement to the fanbase. It honestly reminds me a lot of the 2019-20 Blue Jays. With the Nationals 11.5 games out of a playoff spot and a late-season push unlikely, it’ll be tough to put a finger on what Martinez needs to do to prove himself worthy of continuing to lead this rebuild. Nonetheless, the Nationals have a decision to make with the future of the franchise ready to go.