Jesse joined ESPN Chicago in September 2009 and covers MLB for ESPN.com.
In the first game of the Philadelphia Phillies‘ 2023 MLB postseason run, in the bottom of the fourth inning with the Phillies up 1-0 on the Miami Marlins, Nick Castellanos belted a double. When he reached second base, he dusted himself off, pausing to look into the home dugout — and proudly displayed a single batting-gloved finger on his right hand to his teammates cheering back at him.
Social media exploded, and even his own team’s dugout was confused: Was the Phillies’ right fielder flipping off his teammates from the middle of the diamond at Citizens Bank Park?
Castellanos later said that it was his ring finger he was waving in the air and that the gesture signified he wants a World Series ring to put on that finger, but for his teammates, this was just the latest case of Nick being Nick. This kind of thing is exactly what they’ve come to expect during his two years in Philadelphia. Ask anyone who shares a clubhouse with Castellanos what makes him tick and the inevitable smirk appears on that person’s face. He’s different, they say. But in a good way.
Shortstop Trea Turner put it simply: “He’s one of one.”
“I don’t know if I’ve met anybody like him,” Turner said recently. “He’s different. And he can really, really hit. It’s cool seeing him just do his thing. And regardless of what people think about him, he’s just his own person. So I love him and respect him for that.”
After a down year in 2022, Castellanos has burst onto the national scene during these playoffs. And it’s not just his National League-leading five home runs this postseason for a team that will take on the Arizona Diamondbacks in an all-or-nothing Game 7 of the NL Championship Series on Tuesday night.
Beyond his play on the field and penchant for an attention-grabbing quote or celebration, his endearing relationship with his 10-year-old son, Liam, has also produced heartwarming social media moments that have helped make Castellanos a fan favorite in Philadelphia.
“Every day, being part of this team and getting to understand this city and being able to [spend time] with Liam, I’m loving my space here,” Castellanos told ESPN.
Philadelphia has become a home, something for which the 31-year-old has been “searching” for a long time.
Castellanos was taken No. 44 overall in the 2010 draft by the Tigers, and he flourished at the plate as a doubles machine in spacious Comerica Park. But in his six years in Detroit, he made the postseason only once, in his rookie year, and for the latter part of his stay, he was one of few veterans on a perpetually rebuilding roster.
“I’m a dreamer by nature,” Castellanos said. “When I was drafted as a Tiger, I thought of Al Kaline. I thought I was going to be like him. You don’t always get Plan A.”
Plan B turned out to be a trade to the Chicago Cubs at the 2019 trade deadline, just before he was scheduled to hit free agency the following offseason. Though he quickly became a fan favorite because of his scorching-hot performance at the plate — he hit .321 with 1.002 OPS in 52 games — Castellanos had trouble finding his place as a temporary answer in a clubhouse full of players who were part of Chicago’s 2016 World Series roster.
“With the Cubs, I was a rental player,” Castellanos said. “I was there for two months. I have all these visions and dreams and aspirations and theories on how things should go. But it was not my place to go in and do that because if I vocalized all that, I would have been viewed as a tyrant. That’s also not in my personality either because any leader who inserts himself into that position, that’s not a leader, that’s a dictator. Over history, people don’t f— with dictators.”
Though Chicago had made four straight postseasons, that year the team faltered late and Castellanos again missed out on playing in October. By that offseason, when Castellanos hit free agency, the Cubs were shedding salary instead of adding it, so Castellanos had an open mind in his search for a new home.
He ultimately signed a four-year, $64 million contract with the Cincinnati Reds that included opt-out clauses after each of the first two seasons. Coming on the heels of a career-best season in 2021, Castellanos elected to become a free agent for the second time in three years. Though he called his 2021 season “the most consistent, happiest I’ve been playing baseball” at the time, his performance had put his next contract into a dollar range the Reds were unlikely to spend, and Castellanos was again on the move.
The Phillies didn’t actually emerge as a possible landing spot until late in the winter.
“I did not think that I was coming here during my free agent process at all,” Castellanos said. “It wasn’t [one of] the cities that I was interested in at the time, really wasn’t on the radar. Then Bryce [Harper] reached out to me and said, ‘What do you think? I want this. I want you to be here.'”
Harper’s pitch worked, and over the span of three days in March, the Phillies signed Kyle Schwarber for $79 million and Castellanos for $100 million, remaking the team’s offense (and leaving plenty of pundits wondering about its defense).
Asked if his fit in Philadelphia off the field was everything he had hoped for, Castellanos gave an emotional response that went far beyond the team’s success on it.
“Yes,” he said. “And it starts with the Middleton family. [Owner John Middleton] is a Phillies fan. He’s a Philly guy. That’s the foundation of everything. I truly do not believe that owning this team is a business for him. It’s a passion. If that passion is not there, a lot of time, the things that are underneath it, does not work out. Because of that, he oversaw the hiring of [president of baseball operations] Dave Dombrowski. And I think Dave is tremendous at his job. And what makes him tremendous at his job is he’s such a good people person. He believes in character above individuals.
“Every team is going to talk. I found that the more intelligent the words sound, the faker they are. The more fancy and educated the vocabulary — you’re getting to describe why winning is not now but it is in our imminent future — they’re trying to convince. I didn’t have to be convinced here.
“The one thing that gave me comfort was having pillars in Bryce, J.T. [Realmuto], [Zack] Wheeler, Schwarber and Dave’s track record. I didn’t need to hear any intelligent vocabulary because if I can just look at what’s there, I can understand.”
Such a thought-out and detailed response to a question, any question, is something Castellanos’ teammates have come to expect in their two years together.
“If Casty wasn’t a ballplayer, he’d be a philosopher,” catcher Garrett Stubbs said. “He’ll always ask, ‘Why?’ No matter what. He’s probably the most curious person in the entire world. It doesn’t matter what the conversation is about. You know how little kids will always ask, ‘But why?’ He’s always asking why, and it’s hilarious.”
Across the clubhouse, second baseman Bryson Stott admitted that learning to appreciate Castellanos’ deeper thoughts to even the most routine conversations took some time.
“You could ask him the most simple question like, ‘Why is it 7 a.m. in the morning?’ and he gives you an answer you could probably write a story on,” Stott said. “Sometimes you’re like, ‘Nick, I just want to know what time it is. I don’t need to know about the sun and how everything is moving around.’ Anytime you get in a conversation, you know you’re going to get the most in-depth, full answer you could get.”
Or you could get something off-the-cuff and shocking, in the vein of his ring-finger celebration. During an on-field interview after the Phillies’ division series win over the Atlanta Braves, Castellanos was asked if his fit with the team was something he always needed. Without skipping a beat, he responded, “I mean, yeah, I f— with Philly,” on national television.
“I’m not sure where he’s going with some of those interviews, like a lot of other people,” Dombrowski said with a smile. “That’s Nick. One thing you won’t get is any false pretense. You’ll either like it, or you won’t. That’s up to you.”
There is no denying that Castellanos’ straightforward approach could be jarring in a professional clubhouse. But the mistake, according to those who know him best, would be to judge Castellanos by only his quirky, say-anything style without getting to know him as a teammate.
Rookie center fielder Johan Rojas points to the help his right fielder has provided him all season, from the first day of spring training, to his call up to the big leagues in July, to the October stage. Throughout, Castellanos has been there to show the 23-year-old the ropes.
“He’s been a mentor to me,” Rojas said through the team interpreter. “He’s been good about everything, really. He tells me what to expect in the game and sometimes when I don’t have a good [at-bat], he comes to me to forget about it and focus on defense.
“All I can tell you is he’s a great teammate. He’s always looking to help me. I can’t be more thankful to God for putting me on his team. He’s been an incredible teammate.”
Firmly in his comfort zone in his second year in Philadelphia, Castellanos has grown into a leadership role in the clubhouse and become a fan favorite. Much of what has endeared him to the home fan base is showing how he connects with his son through baseball. First, MLB released a Father’s Day video tribute that showcased a softer, more personal side of Castellanos not many had seen before. Whether it’s his son cheering him on after a clutch home run or a postgame trip across the parking lot to meet fans at Xfinity Live, their interactions this postseason have become part of the fabric at Citizens Bank Park. On the eve of NLCS Game 6, it was Liam who got the bigger ovation when both Castellanoses were shown on the Lincoln Financial Field scoreboard during the Miami Dolphins-Philadelphia Eagles game. Getting to share the journey with his son has added to the feeling of groundedness for the elder Castellanos.
“If what you mean by ‘home’ is I have like-minded individuals that are passionate about being great at their careers, yes, I have found a home,” Castellanos said. “The city of Philadelphia, and the crazy cheering by the fans, is all complementary to that. Because if you don’t have that, everything else is come and go.
“The more comfortable I feel with where I’m at, the more my raw emotions can come out and I’m not worrying, thinking or analyzing about s—. I’m just doing it because everything else is in its place.”
Now, Castellanos and his Phillies teammates have a chance to finish what they fell just short of accomplishing last season — bringing their city its first World Series title since 2008. But Castellanos refuses to let even that lofty goal be his only measure of success.
“There’s two ways to go about it,” he said. “You can look at the positive side and just appreciate the fact you got to be in it and not sound like a spoiled brat, just be thankful for the opportunity to play in the biggest baseball series in the world. Or you can be that much more frustrated and not be thankful about any of it and just want to finish it the right way, and none of the other stuff matters. Where’s the balance?”
Many players would have given the expected canned response to such a question, but it’s an answer that is quintessential Castellanos.
“Nick being Nick,” pitcher Michael Lorenzen said. “He knows how to be himself better than anyone.”
If the Toronto Blue Jays are going to bounce back, tonight’s the night.
After Toronto lost two at home to the Seattle Mariners, the American League Championship Series heads West for Game 3.
The first matchup at T-Mobile Park isn’t an elimination game, but the stakes couldn’t be much higher. It’s essentially a must-win for the top-seeded Blue Jays; only one team in MLB history has ever come back from trailing a postseason series 3-0. Meanwhile, for the Mariners, it’s a chance to get one victory away from the first World Series appearance in franchise history.
Stay here for our coverage — from the pregame lineups to the top moments during the game to our takeaways and analysis after the final pitch.
ESPN baseball reporter. Covered the Washington Wizards from 2014 to 2016 and the Washington Nationals from 2016 to 2018 for The Washington Post before covering the Los Angeles Dodgers and MLB for the Los Angeles Times from 2018 to 2024.
SIX MONTHS AGO, just seven games into the 2025 season, the Toronto Blue Jays arrived in Queens with uncertainty hovering over Vladimir Guerrero Jr.’s future. New York Mets fans, hopeful that their team could eventually land the impending free agent and partner him with Juan Soto, welcomed the first baseman with notably loud cheers at Citi Field to open the weekend series. Guerrero and the Blue Jays had failed to reach an agreement on a contract extension before an arbitrary mid-February deadline, and the drama would not die.
Then, suddenly, it did, hours after the Mets completed a weekend sweep. The deal was historic: 14 years, $500 million without deferrals, the third-largest contract in Major League Baseball history. The Canadian-born Guerrero, signed out of the Dominican Republic as a 16-year-old with a famous name, would be a Blue Jay for life. Guerrero bet on himself by turning down smaller offers and bet on the Blue Jays by agreeing not to test free agency. And the Blue Jays bet on the homegrown star at a massive price, having whiffed on other marquee talents in recent years. The impact was instant.
“We didn’t start playing our best baseball until May,” Blue Jays starter Max Scherzer said. “But if that didn’t get settled, it would be this cloud hanging over our season the whole time. The fact that that was resolved just kind of settled everything down. The outside attention is resolved. It’s no longer, ‘What’s going to happen here?’ It kind of took the elephant out of the room.”
Guerrero, 26, responded with his fifth All-Star season, batting .292 with 23 home runs and an .848 OPS in 156 games. His play, coupled with rebound seasons from George Springer and Bo Bichette and a deep roster of contributors, fueled the Blue Jays’ ascension from 74 wins and last place in 2024 to 94 wins, an American League East title and, now, Game 3 of the American League Championship Series.
The Blue Jays can point to a few possible turning points on their way to a fourth playoff appearance in six years. There was a three-game sweep in Seattle in early May. There was Bichette’s pinch-hit, go-ahead home run in the ninth inning in Texas later that month. But Guerrero’s agreement a week into the season helped pave the way to where the Blue Jays find themselves Wednesday: four wins shy of their first World Series appearance in 32 years.
Down 2-0 after the Mariners dominated the first two games in Toronto, it’s no easy feat. But the goal Guerrero has set for himself hasn’t changed.
“For me my goal always is to win a World Series, to bring the World Series here,” Guerrero said earlier this postseason. “My father, he never had the chance to win a World Series. That’s one of my goals, always been one of my goals, to do that for me, for him.”
THE JOURNEY TO this breakout postseason for Guerrero and the Blue Jays began more than a decade ago. In January 2015, months before Guerrero was eligible to sign as an international free agent, Edwin Encarnación received a call from Alex Anthopoulos, then Toronto’s general manager: The Blue Jays wanted to see a 15-year-old Guerrero, their top target that year, work out again in the Dominican Republic — and they needed to find a ballpark.
Encarnación, coming off an All-Star season for Toronto in 2014, reached out to his contacts and a workout was arranged to have Guerrero face older free agents from Cuba. With Encarnación and Blue Jays officials, including Anthopoulos and international scouting director Ismael Cruz looking on, Guerrero convinced the decision-makers.
“It was something special,” Encarnación said in Spanish on the field at Rogers Centre on Monday before Game 2 of the ALCS. “Vladdy was better than the Cubans. This kid, at 15 years old, showed off against them. He was special.”
That July, the Blue Jays used their entire international bonus pool to sign Guerrero for $3.9 million. Worried about the hoopla that came with being the son of a future Hall of Famer, Anthopoulos asked the team’s media department to hold a low-key event when Guerrero, born in Montreal during his father’s time starring for the Expos, was brought to Toronto for the first time. No news conference at the podium. Just batting practice on the field.
“I was concerned with the last name, the hype and the expectations were going to be out of this world,” said Anthopoulos, now general manager of the Atlanta Braves. “And they were anyway, as much as we tried to play it down.”
Guerrero was not immune to the pressure upon arriving for his major league debut in 2019 as the top prospect across baseball at just 20 years old. The years that followed were not a linear progression. After an AL MVP runner-up season in which he clubbed 48 home runs with a 1.002 OPS in 2021, his first year as a full-time first baseman, Guerrero hit 58 home runs with an .804 OPS over the next two years. Then came another breakout last season: a .323/.396/.544 slash line with 30 home runs in 159 games to raise his value heading into his platform year.
“He’s not easily distracted,” Blue Jays general manager Ross Atkins said. “He’s still very human, and I think the hardest part, from my perspective and my view, that Vladdy’s had to deal with is the expectation. Not the distractions off the field or the attention. And he embraced the expectations.”
This year, the pressure was on Guerrero to finally perform to those expectations in the postseason. He entered the AL Division Series against the New York Yankees 3-for-22 with two walks, five strikeouts and no home runs in six career playoff games — all losses — spread over three separate wild-card series.
Guerrero quickly discarded that history in Game 1, swatting a solo home run in his first plate appearance of the postseason. In Game 2, he cracked a grand slam that will long be replayed on Rogers Centre highlight reels. He finished the series 9-for-17 with three home runs and nine RBIs as the Blue Jays eliminated New York in four games.
“I think he’s improved a lot in all aspects,” Blue Jays catcher Alejandro Kirk said. “The experience, how he’s matured as a person. He’s no longer the 20-year-old Vladimir when he debuted. Now he’s Vladimir.”
VLADIMIR VASQUEZ WATCHED the Blue Jays close out the Yankees last Wednesday from his restaurant 5 miles north of Rogers Centre. Born in the Dominican Republic, Vasquez moved to Toronto when he was 11 years old in 1990 and quickly became a fan of the early-’90s Blue Jays championship teams. He opened Cabacoa, a Dominican restaurant, a year-and-a-half ago — a sign of the city’s growing Dominican community.
“I’ve been following Vladimir Guerrero Jr. since he was in the minors,” Vasquez said. “It’s funny because his dad was the only older Dominican Vladimir I knew growing up. But it’s important for the community, for the Dominican community, to have somebody who’s that good who’s going to be here long term.”
It’s part of the responsibility Guerrero shoulders beyond playing first base and batting third. He’s the only Canadian citizen on Canada’s only MLB team. His No. 27 jersey is the one Blue Jays fans wear from British Columbia to Newfoundland. He’s the player the Blue Jays committed to as their cornerstone through his age-40 season in 2039 — 20 years after his debut — with hopes he’ll end up with his own Hall of Fame career.
“I look at Vladdy long term because I’ve gotten to play with the greats,” said Scherzer, an 18-year veteran and three-time Cy Young Award winner. “I’ve gotten to play with so many great, different players over my career. For me, he kind of fits this Prince Fielder-Miguel Cabrera mold. He’s kind of a hybrid between those two.”
In the short term, the agreement was an exhale. Perhaps, as Atkins said he’d like to think, the Blue Jays would’ve found their footing without Guerrero signing the extension. The pieces were in place two years removed from an 89-win season. But that variable, which had lingered from the day Guerrero reported for spring training, was removed.
Six months later, the Blue Jays, behind their franchise pillar, are breaking through.
“I think it kind of showed our fan base and the league kind of what we’re trying to do here short and long term,” Blue Jays manager John Schneider said. “And it just kind of clears a little bit of a cloud around a really good player and allows the team to say, ‘OK, this is our guy, this is what we’re going to do.’ I think it kind of freed everyone up.”
If the Toronto Blue Jays are going to bounce back, tonight’s the night.
After Toronto lost two at home to the Seattle Mariners, the American League Championship Series heads West for Game 3.
The first matchup at T-Mobile Park isn’t an elimination game, but the stakes couldn’t be much higher. It’s essentially a must-win for the top-seeded Blue Jays; only one team in MLB history has ever come back from trailing a postseason series 3-0. Meanwhile, for the Mariners, it’s a chance to get one victory away from the first World Series appearance in franchise history.
Stay here for our coverage — from the pregame lineups to the top moments during the game to our takeaways and analysis after the final pitch.