5. Dave Henderson
Henderson played 111 games for the Red Sox. He had his best years post-Boston with the Oakland A’s, was drafted and started his career with the Seattle Mariners and had stints with the San Francisco Giants and Kansas City Royals.
Hundreds of players played more game with the Sox. Hundreds of players had better numbers. But aside from a couple, I don’t think that there have been as many that made such an impact as Henderson did in his one season in town.
I’ve written about Henderson ad nauseum. While Roger Clemens made me like baseball and the Red Sox, Henderson made me love the sport and the team. His homerun in the top of the ninth of Game 5 of the 1986 ALCS is nothing short of spectacular.
Starting center fielder Tony Armas gets injured early in the game, Henderson—who hasn’t played in weeks—gets inserted into the game. He tries to make a wall climbing catch but ends up knocking the ball OVER the fence. Goat horns for a guy who didn't deserve them. Up until this point the Sox are absolutely awful in all facets.
He comes up in the ninth with a man on first, the Sox haven’t done shit in the batter’s box all day, and he’s facing California’s closer Donnie Moore, who was pretty damn good. Henderson looks foolish on two pitches and then launches one into deep left field, the Sox take the lead. The Angels tie it in the ninth and Henderson wins it with a sac fly in extras. The Sox go on to complete the comeback in Fenway by winning the last two games.
From goat to GOAT in one game for a player who was anonymous before the game started is a journey, man.
But that’s the great thing about sports, baseball in particular and life as a whole. You need to be ready for your time. It comes quickly and once it comes, you need to grab it.
Imagine being Dave Henderson and for years you’re stuck in Seattle playing for a shit team in a shit stadium that no one cares about. You tell people you’re a Mariner and they ask you how long you’ve been in the Navy. Finally you’re traded to a contender and for some reason your new manager is choosing to play a broken down Tony Armas in front of you. He’s slower than you, he’s fatter than you and he can’t do anything better than you.
So you sit on the bench and you wait. And wait. And wait. Why did this team trade for me if they’re not going to play me, you wonder. Finally old man Armas injured himself and you hear the bell. First thing you do is knock a ball over the fence, the Angels are starting to celebrate and it looks like your one chance is down the drain.
I know that 2004 was bigger. And I completely understand that we’ll never, ever, ever live through something like that again. But the Henderson homerun is the first time I’ve experienced the magic of baseball.
I remember everything about that moment. I remember sitting on the love seat in my den while my Mom and brother were on the couch. It was a Sunday around 5:00 and for some reason my Dad was making dinner and was yelling at us to get to the table because the peas were getting cold. I remember telling him that Henderson was up and all the team needed was a homer and him saying that they’d blow it (my Dad never really liked the Sox too much). When he hit that homerun everyone in the den whooped and cheered and my Dad got pissed because soon the potatoes and steak were going to get cold too.
By the time the game ended, dinner was freezing and as we decided what to do for eats; my grandmother, aunt and uncle showed up with Chinese food AND McDonalds.
My grandmother, uncle and aunt never showed up unannounced at our house. Certainly not with McDonalds and Chinese food. It was probably the greatest afternoon of my life. Probably not for my Dad though.
So yeah I’ll be chasing that dragon for the rest of my life. Henderson died more than 10 years ago and I always wanted to meet him and let him know how much that one swing changed my life. I wanted to thank him for giving me the undying love for the sport of baseball.
4. David Ortiz
This is where things start to get tough. I love David Ortiz. Who doesn’t? This person, who I do not know, was integral in making me happy for 15 or so years.
And that’s kinda weird when you think about it, right? Sports fans have no real skin in any game that’s played. When the Sox won the 2004 World Series, I didn’t get a raise at work. I wasn’t gifted a new car. I didn’t get a championship ring.
But it made me insanely happy. And if you’re a Sox fan, it probably did the same for you too.
There’s no rational answer for why that’s so. I guess you put a lot of time into following the team. You think about all of the people whom you’ve seen games with or discussed the team with. Maybe you think of the city or the region and how proud you are of living here. While there’s no tangible reason for being so deliriously happy, you are.
Sports aren’t logical.
That’s a hard concept to wrap your brain around because we’ve been told over and over and over again that it is. People have said if you work hard and practice, you’ll be great. That’s true but only to a point. No amount of practice is going to allow me to hit a 100 MPH fastball.
The parts of sports that I think we love are the random aspect. Things that come out of nowhere. Things that surprise us. I like the Dodgers a lot and they’re presently 8-0 and if they win the World Series in October it’s kinda like “yeah, okay, I knew that was going to happen.” (Editor's note: this is not what it was like. Jesus, I couldn't have been more off if I tried. Favorites or not, the 2025 World Series was amazing.)
But if the Pirates or the Reds win? Now that’s a story.
Which leads to David Ortiz (this preamble has a point). When Ortiz was released by Minnesota and signed by Boston (and holy shit can you imagine the amount of ink and tears spilled if the reverse occurred?) it was barely mentioned in the papers. Maybe a two paragraph story by Gordon Edes and for some reason the personification of the turd in every punch bowl, Dan Shaughnessy (who seems okay now) called Ortiz a “fat piece of you know what”. I’m not sure why he wrote that but he did and all I know is that I’m glad he’s not a Red Sox scout.
In any event Ortiz started slow. He was stuck behind Jeremy (not Jason) Giambi for playing time. He wanted out but GM Theo Epstein asked to give him more time and that things will shake out. They did. And Ortiz started hitting, the Sox started winning, Giambi was traded to Philly and Papi (as Ortiz was called) settled into a decade and a half of dominance at DH. He was elected to the Hall of Fame a few years ago based on his incredibly clutch performances.
There are two things at work here:
1. How did Epstein know that Ortiz would be this fucking good? If you believe the story, when Pedro Martinez heard the Twins were releasing Ortiz he called Epstein and told him to sign him. Which, if true, makes sense because Pedro is God almighty. But if it isn’t true or if Pedro isn’t all-seeing and all-knowing (there’s no proof that isn’t true too) then how did Ortiz go from being a Twins washout to a Hall of Famer? The more cynical of you will say steroids. And maybe that has something to do with that.
But I think that more likely reason is that it was just luck. No one knows anything, really. You can try but you’re not going to fully know. And that’s what makes sports so great, that unknown.
This leads me to:
2. David Ortiz was absolutely fantastic* when the chips were down and you needed a big hit. The 2004 playoff run stalls without him. That’s a fact. And in subsequent years whenever a big hit was needed, Ortiz usually was the fat guy in the red suit delivering it. Baseball front offices have statistical analyst departments that have ballooned to 250+ people. People who own these billion dollar enterprises tend not to want a lot of surprises in their investments. They want to know who does what when and why but also who does it the best.
* How awesome was it for almost 20 years, Boston had the two clutchest guys playing for their teams in Ortiz and Tom Brady? Talk about luck, us Boston fans are lucky to see two of the greatest ever work their magic every single day. It was incredible.
The front offices have been working on cracking the “clutch” code forever. So much so that a majority of them have said it doesn’t exist mostly because they can’t prove it mathematically. I understand that. I get why they’re trying to figure this problem out, I get why they can’t wrap their brain around it and I completely understand their conclusion.
But they seem to be missing the biggest part of sports and that sometimes, it’s illogical. You can show me math concepts that “prove” being clutch doesn’t exist. I probably won’t understand them or how you came to that conclusion but I’ll trust that you mathed your math correctly.
But put Ortiz up in the bottom of the ninth, with two guys on base and the Sox down by a run and I know, I fucking KNOW that he’s going to deliver. It’s faith mixed with illogic mixed with magic. I know he’s going to come through.
Because that’s sports and in particular, that’s baseball. There was an early 90s gangsta rap group
called Above the Law. They were NWA protégés and to be honest, they weren’t very good. But one of their songs had a line that said, “It’s not what you know, it’s what you can prove.”
And for a guy like David Ortiz, it’s the exact opposite.
3. Mookie Betts
Number three is a person whose name is triggering to a fan of a certain age.
Let’s begin with one truism: the Red Sox never HAD to trade Mookie, they wanted to because they didn’t want to pay him. Fenway Sports Group is worth $7 billion yet they felt that the generational player, who came up through their minor league system, who was beloved by the fans and routinely posted Hall of Fame numbers wasn’t worth it. Okay. Fine.
They compounded their stupidity by pretty much letting all of MLB know that Mookie was available and entrusting a very green President of Baseball Operations, Chaim Bloom, with the responsibility of getting the most that he could for the star. Already with a limited market, Bloom decided to make a deal with his former boss-who is probably this generation’s top PoBO who absolutely destroyed him.
And not only that, but due to Bloom’s indecisiveness the deal dragged on for days. The deal sent Betts and David Price (who Bloom insisted on LA taking at the last minute almost blowing up the deal) for Jeter Downs, Alex Verdugo and Connor Wong (another last second substitution after the pitcher they wanted’s arm didn’t look great, actually it was fine and he pitched pretty well for the next two seasons).
To review in exchange for a generational talent they used him as a sweetener to take a bloated contract but also got a mercurial outfielder who was involved in a shady situation where a sexual assault occurred, a highly regarded infielder with a funny (for Boston) name and a catcher. In a farm system that famously can’t produce a pitcher to save its life, the best chip they have can’t fetch even a lottery ticket arm.
Fucking Chaim Bloom, man. Jesus.
You know what happened, the Sox nose dived, finished last three of the next five seasons. Downs sucked and was released. Verdugo wasn’t much better and was an asshole to boot. They sent him to the Yankees. And Wong is probably a platoon catcher at best.What makes this trade even more crazy as that the Sox insisted that it had nothing to do with his new contract but that this was a “baseball trade”. I hate when people think that we’re stupid. Fuck. You.
In his six years in LA, Betts has continued to put up big numbers, lead his team to the playoffs every year and was on a World Series winning team twice (Editor's note: actually thrice). Pretty savvy trade Chaim! Great showing, buddy.
Let’s focus on the positives and that is Mookie Betts was probably the most dynamic player the Red Sox ever produced. He could hit for average. He could hit for power. He had speed. He played great defense and was versatile. And to top it off, he had a cannon for an arm. He was a five tool player.
Not only that but he seemed like a really good guy. There were a few stories out during the World Series where after the games he and his brother (I think, maybe his cousin) would go and bring trays of food the Boston’s homeless. He told reporters not to say anything but it still slipped out. He also had a strong bond with the Boston fans, which as a Black athlete is important. I know it shouldn’t be important, but African American stars STILL say they hear racist shit in Fenway all the time. And that sucks. Mookie, hopefully, could have turned some of that perception around. Sending him away was a major mistake.
Not only that but in the last 20 years, the Sox have fallen out of favor with the New England fandom. It’s been all-Patriots, all the time. I guess you could attribute that to the 800 pound gorilla known as the NFL but there are still baseball strongholds in New York, LA, St. Louis. Boston was one of them but it’s not anymore.
Tom Brady had one foot out the door. Jayson Tatum wasn’t JAYSON TATUM yet. Patrice Bergeron was also close to retiring. Mookie Betts could have stepped into Brady’s shoes and lifted the Sox. But the Sox didn’t want to pay him, so now he’s LA’s “problem” now.
The best thing I ever saw Mookie do was an August 2018 game against the Blue Jays. JA Happ was on the mound and he owned the Sox. I’m pretty sure Boston was losing but Mookie came up with the bases loaded. He proceeded to battle Happ for 13 pitchers, fouling off everything thrown at him until he found his pitch and launched it over the Monster. He let out a yell and Fenway was deafening in their MOOOOOOOKIE chants.
I can’t remember a louder regular season game.
And that’s what Mookie brought. Hard nose excitement from a guy who played his ass off day after day. HoF owner Bill Veeck said that paying a superstar won’t handicap your team’s finances but paying for mediocrity will. I know that the McKinsey bean counting drones in Fenway’s front office bowels don’t get that but it’s should be tattooed on their forearms Memento style.
Baseball is entertainment. Fans want to see the best players, salary be damned. If you’re not going to spend on Mookie, then who are you going to pony up for? I think that’s what broke me. As I said in the Ellis Burks entry, I had been dying for the Sox to get a five-tool, exciting player and they finally got him. He was as awesome as advertised and then they wouldn’t pay him what he was worth for some reason. I understand why, I truly do, but I won’t ever agree with it
I will always love the Red Sox and while this ownership has been good they do a lot of stupidly avoidable things. I knows this sounds crazy but no how many more championships this group wins, they can never remove the Mookie stain.
2. Pedro Martinez
The way that I, and anyone else lucky enough to witness the Pedro experience, talk about him like he’s a cross between Babe Ruth, Michael Jordan and Paul Bunyon.
When you factor in the era that Pedro played in: height of the steroid game, every park shrunk, strike zones were minuscule, the insane numbers that he posted are even more crazy. It’s cliche to say that he put up cartoon or video game numbers, but he did.
From 1997 through 2004, no one was better. And it’s not like he made his bones pitching in the American League Central, he pitched in the East where he was facing the Yankees four or five times a year in the midst of their last dynasty.
Honestly. Just go look at his numbers on baseball-reference: https://www.baseball-reference.com/players/m/martipe02.shtml
Pedro pitched in an epoch of pitching giants: Randy Johnson, Greg Maddux and Roger Clemens. These are four of the all-time greats. They are the Beatles of pitching. I don’t think there will ever be another run of pitchers like this and I haven’t even gotten into the second tier (the Rolling Stones, if you will) like Glavine and Smoltz and Schilling and Bartolo Colon and the three aces in Oakland and Kevin Brown. All legit, absolute stud hurlers.
But for five years, Pedro was the best of them all. Whether you think the most talented Beatle was Paul, John, George or Ringo; that’s who Pedro was.
He wasn’t just a compiler either, as the games got bigger, Pedro got better. In the 1999 ALCS when he faced off against Clemens with Boston needed a win, who was on the mound raising his arms in victory? I don’t like to prove one person’s greatness by denigrating another, but Clemens left that game by the third inning. The likes of Brian Daubach and Troy O’Leary flummoxed the big Texan while Pedro sat Jeter, Bernie Williams, Paul O’Neil and more on their asses.
Pedro did something that Clemens couldn’t do and that was inspire confidence. When Pedro was on the mound, it was an upset if he didn’t succeed. Even later in his career, the man just knew how to simultaneously slow down the moment and dial up his performance. In comparison, Clemens would psyche himself up so much that he’d lose control.
Pedro never, ever lost control.
You can spend hours talking about Pedro games, like the time he struck out 18 Yankees in a one-hitter (a "lucky" Chili Davis homerun, he admitted is eyes were closed when he connected) at the Stadium. Or when he mowed down Devil Ray after Devil Ray in another one hitter where Gerald Williams tried to fight him (and lost).
The thing was every single Pedro start was appointment television. There definitely was a buzz when he started becausese you never knew what was going to happen. “Pedro’s going tonight in Seattle, looks like it’s a three-Dunks day. Keep ‘em comin.”
If you were lucky to have tickets on the game he pitched, everyone was your best friend. The first date I ever took Aly to was a Pedro start. Both the girl and that night’s starter got me tingling. I ended up marrying one of them.
Dan Duquette traded for Pedro Martinez twice. Once when he was the GM of the Montreal Expos (for Delano DeShields) and obviously once when he had the same position with the Sox (for Brian Rose and Tony Armas Jr.); so he understood how special Pedro was even before most of us.
This skinny dude shows up and he doesn’t look like a Major League pitcher, right Tommy LaSorda? But he has so many pitches, a fastball that belies his body—I guess pitching really is about physics not strength. A breaking ball that makes the “pitching is all about physics” idea a lie. Curves that buckle knees and unbuckles belts. He had it all and he could throw it by a hitter who more than double his weight and was in the midst of a steroid cycle.
I’ve said it before and I’ll say it again, Pedro is a god. There will never, ever, ever be anyone like him again. Especially for the time he showed up and pitched. Baseball was the most important thing in Boston at the time and it wasn’t even close. To have an all-timer taking the hill every five days was an absolute privilege.
It always used to blow my mind that there were media members (WEEI sports screaming bigots Dennis and KKKalahan come to mind) who seemed to despise Pedro and how he pitched, nothing was good enough for these assholes and it makes me happy that Pedro is always going to be remembered and loved while these guys have been forgotten and relegated to trashcan of the past. If you cant appreciate or recognize transcendent greatness, what are you even doing?
There are a few reasons why the 2004 team is one of my favorite teams. The obvious one is that they won the World Series for the first time in 86 years, that’s obvious. The second was that this was a team of guys who had been together for years: Pedro, Varitek, Derek Lowe, Nomar, Manny, Wakefield, Ortiz, Damon and they came so fucking close the year before. You know how it is, teams that get that close, everything needs to break just right and it doesn’t happen two years in a row.
So for Grady Little to kick that away, it was like, logically you had a feeling that that was going to be it. No matter who they added, if they didn’t win in 2003, they’re not going to win it with this bunch. You get one chance.
So coming into 2004, there was a lot of pressure for this group of guys to win it. To make matters even more difficult was that a lot of players (Pedro primarily) were on the last year of their contracts and many weren’t going to return. The odds were stacked against them and this was really it.
They won the wild card, they were down against the Yanks but they were resilient and awesome and they fucking won. The team that was looking square in the eye of another really talented Sox team (probably the most talented, TBH) that came up a little short. But they won. They fucking won.
And Pedro, already a no doubt Hall of Famer, got his ring. He led Boston to the promised land just like he said he was going to do.
At the end of the day, if you don’t love Pedro, you don’t love baseball. It’s that god damn simple.
1. Manny Ramirez
Before we start, it’s important to remember that I’m not basing these rankings on what kind of humans these people are. To say Manny is complicated is to completely devalue some of the shitty things he did off the field. I get that and recognize what he did and it sucks.
With that preamble out of the way, I’ve never seen a better hitter in my life than Manny. The way Manny hit was like the way Prince played guitar or Michelangelo painted or Plato thought. He was an absolute genius. The way he smashed pitch after pitch with violent control was astounding.
Trying to hit a pitched ball with equal parts balance and power might be the hardest thing to do in sports. Manny may have looked bad once in a while but a majority of those times were done purposefully. Teammates were astounded how Manny would set up opposing pitchers by looking bad at during one at bat only to demolish that same pitch innings, games, months, YEARS later.
Sports isn’t about athletics excellence, it’s about mistakes and exploiting them. There’s a perception that athletes don’t make mistakes on the field, court or ice. They do, just less so than us regular folks. That’s why they’re pros.
But pros make mistakes and the stars are the ones who exploit those mistakes. I’ve never seen a player, in any sport, that could absolutely demolish a mistake like Manny Ramirez. Leave a fat pitch over the plate? It’s on Lansdowne Street. Try to throw a pitch that you thought made Manny look silly two games ago? Dummy, he was setting you up and now the game is tied.
Manny’s home runs were legendary. I don’t recall any cheapies. They were all the Platonic (that’s two references to Plato in one Manny essay!) ideal of a home run. They were high, arcing shots that left the field in .006 seconds. Everyone knew they were gone the minute bat hit ball.
I remember there was a game when I was sitting in the bleachers against the Blue Jays and he hit a bomb that I swear hit the Pike. I was legit worried that there was going to be a 15-car pileup. Turns out it didn’t hit the pike and it was “officially” one foot short of the Sox’ longest recorded homer hit by Ted Williams. The story was Globe nostalgia humper and hater of anything recent, Dan Shaughnessy said that there was no way Manny Ramirez was beating Ted and that the homer was one foot short. I’m not sure if it’s true but it wouldn’t surprise me if it was.
More than David Ortiz or Pedro Martinez, the Boston media couldn’t understand Manny. And that turned into contempt. There were some Manny friendly stories that would leak out, teammates couldn’t believe how hard Manny worked at hitting. Fielding, like Williams, not so much. I think it was easy to talk about how goofy and dopey Manny was, and I’m sure he was, but you don’t make it to the Majors by being a lazy dumbass.
He wasn’t Trot Nixon or Jason Varitek, a Dirt Dog, he was a fun guy who took things seriously but wasn’t wound tighter than the inside of a baseball. Sometimes it’s okay to see an MLB game for what it is, a game. One of 162 (more if you count Spring Training and the Postseason), it’s okay if you, the left fielder, cutoff a throw from your center fielder Johnny Damon. It’s awesome if you make a leaping catch at the wall, slap someone a high five in the bleachers and then whirl around to double an Oriole off of first. It kinda cool to stop a game and take a leak in the Monster.
We remember that stuff because it’s cool and fun and unique. Because it ultimately forces us to remember that these are games and there are no real consequences at stake. It’s just a bunch of millionaires playing for 30 billionaires while less fortunate people watch and recall what it was like to do the exact same thing when they were younger.
We pay a lot of money for nostalgia in this country.
The Manny experience ended the exact way it was supposed to, him shooting his way out of town. You didn’t think he was going to get his number retired, the Sox would give him a Mazda Miata convertible and he’d ride off into the sunset did you?
That’s not Manny being Manny, that would be Manny being someone else. And we never wanted that.
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