My Favorite Red Sox Players 5-1

 

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.

I know that these entries are supposed to be about the joy that these ballplayers bring me. And Markus Lyn Betts brought me nothing but joy in his six seasons in town. But the way it ended here, it’s going to get rough talking about that again. Bear with me.

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.

My Favorite Red Sox Players 10-6

 

10. Mo Vaughn

In the early 90s, the Red Sox had a problem. The perception around the league, which was more Black than it is now, was that the Red Sox didn’t want Black players. It was hard to argue as Ellis Burks was the only African American on the roster for a year or two.

Black players were straight up telling reporters that there was no way that they’d play for the Sox because the organization and the city made them uncomfortable. As a fan of the Sox and Boston (Massachusetts has been my home forever), that really bummed me out. I’m not Black, so I can never fully understand what they were saying but it made me angry.

Not angry at Black players of course, but angry at the situation as a whole. The Sox had to be aware of the perception of the city, why the fuck weren’t they being more open to Black players? Every time the press asked about it, they’d get blown off. Why didn’t they care?

Then Mo was promoted. Unlike the more shy Burks, Vaughn came up and immediately began asking the tough questions. “Why weren’t there more Black players in the clubhouse?” “How come Black fans don’t feel comfortable in Fenway?” “What is this organization doing about it?”

Finally a person who got it. Predictably older columnists, like Will McDonough, fought back. Some fans told him to essentially “shut up and hit”. But Mo kept talking. Louder and louder. Until someone did something.

The thing is, unless Mo was producing, no one would listen to him. But he was hitting, he hit for average. He hit long bombs. Drove in runs. Pretty much anything offensive that the Sox needed him to do, he did. He won (actually probably stole) the MVP in 1995 from Albert Belle. Reporters hated the notoriously prickly Belle and I’m convinced the votes for Mo were actually votes against Belle. Though TBH John Valentin had a case to beat both of them.

If I was a Cleveland fan, I’d probably still be pissed. But I’m not, so sucks for Belle, I guess.

Mo never delivered the ultimate prize for the Sox, no matter who his running mate was—Jose Canseco, Nomar to name a few—but he kept trying. In 1998 Mo knew he wasn’t going to get the money he felt he deserved in Boston so he went to Anaheim and became an Angel. He had a decent first year there, then got injured, gained weight and bounced to the Mets for his last few seasons.

But Mo Vaughn was a catalyst for change in Boston. He showed the league that Boston can embrace an opinionated Black man. Mo set the stage for players like Pedro, Manny, Ortiz, Betts, players of color who spoke their mind. If he won a few championships maybe he could’ve been our generation’s Bill Russell? But we should still honor what he did both on the field and off.

9. Tim Wakefield

Everyone thinks they’re a good teammate. But that’s probably not true. If you’ve ever been on a team you’ll know that there are anxieties, jealousies, selfishness. For all of the rah-rah, "we're a team!" stuff that gets thrown around any locker room, at the end of the day, sports is kind of a selfish pursuit. This is especially true when things start to go south and the team is floundering. You end up playing for yourself in the hopes you get noticed so you can get off this dumb team.

But every once in a while there’s a person on your team who’s relentlessly positive with out being corny, helpful without being a nag, someone who continually does the right thing and isn’t expecting anything back.

I never made the Major Leagues but I’ve read/heard enough stories to know that every team is filled with ultra Alpha type athletes who have never had a bad thing happen to them on the field. Guys whose outwardly confidence is high into the stratosphere and are used to being the best player in any team they’ve been a part of. They’re so good they’re not expected to be good teammates. That’s a job for shitty players.

Getting to the Majors and learning to be a good teammate and sacrifice for the benefit of the other players, that’s not really a part of most athletes' tool box. But every so often its obvious when a team has a good guy like that truly puts team first.

On the Sox from 1995 until 2011, that guy was Tim Wakefield. His first year in Boston he was picked up off the scrap heap—Pittsburgh dumped him in Buffalo and the Red Sox were desperately in need of starters so they grabbed him. Wakefield pitched a game in Anaheim limiting the Angels to a few hits then shut out the A’s TWO days later in Oakland. And he was off. I’ve seen Clemens, Pedro, Schilling, Beckett, Lester, Sale and others pitch but Wakefield going 14-1 for a stretch in that season for the Sox was truly unbelievable.

He was a mainstay of the pitching staff for the rest of his career. He worked out of the pen as a mop-up guy, a closer, a seventh inning bridge. He was a member of the starting rotation. He was a spot starter. Whatever he had to do, he did. Sometimes he was really good, sometimes he was really bad. Sometimes I couldn’t wait for his next start, other times I wondered why the Sox were employing a knuckleballer. But I never doubted that he gave everything to the team.

When the Sox needed innings in Game 3 of 2004 ALCS, Wakefield gave it to them. Without his sacrifice and a rested bullpen, the Sox don’t win four straight over the Yanks. He was left off the 2007 World Series roster, Wakefield didn’t raise a stink. He just cheered on his teammates from the bench.

The lowest part of his career had to be giving up the walkoff homer to Aaron Boone in the 2003 ALCS. Apparently he was weeping in his locker wondering if he’d be his generation’s Bull Buckner. Like Buckner, Wakefield didn’t deserve those goat horns and luckily it never came to that for him. Tim Wakefield was beloved by New England. In his last year he made the All-Star team and then left the mound for good. He worked for NESN almost immediately after his retirement so it seemed like he never left us.

On the last day of a miserable 2023 season, Tim Wakefield passed away. The sadness that enveloped Red Sox nation was immense and heartfelt. Wakefield may have been from Florida, but he was like one of us (hell, we named a town after the guy!) and whether it was because of his countless hours of charity or the way that Wakefield was so brave going to he mound armed with nothing a knuckleball and a dump truck full of resilience, he seemed like the type of guy you wish you could be.

Wakefield was a rock.

8. Dwight Evans

If you have a brother you might share a bunch of stuff: a room, toys, clothes. But the one thing you don’t share are your heroes. You can both like the same player, my brother and I both worshipped Bo Jackson and Rickey Henderson, but inevitably one person likes the player a little more and he becomes “yours”.

When my brother Jay and I were younger, I thought Jim Rice was the best and he really liked Dwight Evans. I’m not sure why he did but he talked a lot about Dwight Evans. I liked Dewey too but eventually Jay moved on to Don Mattingly (he’d kill me if he knew I was putting this out into the universe) and then others, but Evans was his first.

While I told you about voraciously defend Jim Rice from 6-4-3 jokes, I was also watching Dewey and getting a real strong impression for him. Truthfully he did a lot of stuff Rice didn’t do, he hit for a higher average, he seemed a little faster, defensively he was amazing and he had a cannon for an arm. Rice had a little more power (though Evans wasn’t a slouch) and he also had a few years where he put everything together and had a few monster seasons. Rice had higher highs but lower lows than Evans and that’s probably why he’s in Cooperstown.

But Evans deserves to be there too. I hate comparing two worthy HoF players but Evans played longer than Rice, was more consistent, his drop off wasn’t as sharp. And like I said, his defense was unparalleled. No one ran on Dwight Evans. And the catch he made in Game Six of the 1975 World Series? Amazing. Carlton Fisk doesn’t become CARLTON FISK without that catch. If that didn’t happen then what does Robin Williams talk about to Matt Damon in “Goodwill Hunting”? Not only does Fisk owe Dewey something but Ben Affleck and Damon do as well.

In any event it wasn’t just Evans’ production that everyone loved. He had a long road from prospect to All-Star. He got beaned in the head which resulted in a massive concussion and eventually messed with his confidence at the plate. He had his entire swing remastered by Walt Hriniak mid-career, which no one liked, especially Ted Williams. When the greatest hitter of all time calls you out, it must be tough.

But he worked hard and improved every year at the plate. Getting on base, hitting bombs (remember when he hit a homerun on the first pitch of the 86 season off Jack Morris?), driving in runs. He showed you can improve and excel with age. As the years went by, he became a New England institution. But it wasn't just the production, it was the other things. Like yelling “DEWWWWWWW!” when he was at bat. It was the Selleck-esque mustache. It was imitating his batting style—the toe tap, leaning all the way back before uncoiling—during Wiffle Ball. It was knowing that a right fielder isn’t the shittiest player on the field, with your arm and glove, you can make a difference.

After the Sox let him go he played a year on Baltimore, which was weird to see him in Oriole orange, but the California kid came back to the Bay State.

A few years ago I saw him at Capitol Grille here in Burlington. I was with my wife and another couple and I whispered to them, “holy shit, that’s Dwight fucking Evans” and before they could answer I yelled, “DEWEY!” He turned around, pointed at me, said “Hey!” and asked me what I was eating. I think I said steak and he said, “great choice” then floated away.

I was beside myself. Dwight Evans asked me what i was eating. And I called him Dewey, a name I’ve heard that he absolutely hates. Who gives a shit, we’re best friends now.

I wish I could ask my brother what he thinks of Dewey. Whether he still likes him a lot, whether he cares if he gets into Cooperstown. But that’s impossible because he passed away a few years back. And that’s okay because whenever I think of Evans I think of my brother as a little kid talking about him, mimicking him in the backyard and that’s enough.

It just makes me feel good. Isn’t that what baseball is supposed to do?

7. Jackie Bradley Jr.

Remember the controversy when JBJ made the big league team in 2013? Some people were worried that he wasn’t ready others were afraid that the Sox burnt a year of his eligibility and that he’d be a free agent sooner.

I was all kinda dumb. Turns out he wasn’t ready for prime time and the eligibility thing didn’t even matter. FTR, I was one of those people wailing about the eligibility. Nothing like a little indentured servitude masquerading as “doing what’s best for the team”!

Anyway, Bradley went to Pawtucket after those first couple of weeks and came up for good in 2014. For some reason I was all in on the JBJ experience. I knew he wasn’t the best overall player on the team, but I spent a lot of time wondering how good he could be.

What made him so confounding was that for three weeks, he’d absolutely carry the team offensively. Homers, big hits all over the place. Then you’d start to settle into thinking that Jackie has turned a corner and while he might not hit .600 for the rest of the season, the way he’s swinging he could easily reach half that.

Then he’d go into a six week funk where you wonder if he’s ever seen a baseball before much less hit one. He was the ultimate seesaw player. I think it was part of the lack of consistency that made him so appealing. Because even when he’d suck, you knew he’d eventually snap out of it. You just never knew when. Every day I’d check the box score to see whether yesterday was the day that JBJ was going to get on track. “0-4, not today, I guess. Maybe tomorrow.”

The one thing that never ebbed was his defense. I’ve been watching the Sox for longer than I care to admit and JBJ was the best defensive player I’ve ever watched. When JBJ was in his prime, I was addicted to Twitter. It was a different time and the app didn’t suck nearly half as much as it does now. But back in the day you could really cultivate what you wanted your feed to be and I mostly filled mine with funny people and sports. Baseball Twitter was amazing because the moment something happened, you saw it 40 million times on your feed. Big hit. Big pitch. Big catch. It didn’t matter, watching a game while scrolling Twitter was a lot of fun and I miss it.

The reason why I’m talking about Twitter is because JBJ was on my feed constantly with some sort of gravity defying catch. And like I said, I didn’t see it once but multiple multiple times. From different angles, in slow-mo, set to a song. I saw a lot of Jackie Bradley Jr. and his feats are imprinted in my brain. Does that have something to do with how I see him as the greatest defensive outfielder in my life? Maybe. But also hear me out, he just was.

There's a baseball cliche that says, "defense never takes a holiday" and JBJ was the personification of the argument “do you take a guy out of the lineup if he’s not hitting but he’s saving runs defensively?” In other words, how much does defense means?

Apparently a lot. I didn’t care that he was batting .230, I just wanted to watch Jackie rob homers and make sliding catches and gun people down (he had a very strong arm, which was nice after years of Johnny Damon, Coco Crisp and Jacoby Ellsbury). I just wanted the guy to hit because I was worried to how long a leash the Sox would give him.

At the end of the 2020 season the Sox sent him the Milwaukee (it was the very last transaction before the lockout) and for a year, and he was someone else’s worry. They brought him back a season later but he was cooked. Boston released him and he bounced around for a few teams. He played for the Long Island Ducks last year and hasn’t officially retired, but he’s pretty much done.

When looking back at his career, it’s nothing short of a huge success. He was an All-American at the University of South Carolina where he won an NCAA World Series. He was part of the Big Red Sox Machine of 2018, was ALCS MVP that year, won another ring in 2013, was an All-Star in 2016 and made over $55 million.

How can you not look back at that and see a success? Baseball is a tough fucking game full of inconsistencies, JBJ was able to navigate those into a nine-year career.

Not too shabby.

6. Nomar Garciaparra

It’s hard to say that Nomar came at a time when the Red Sox needed a superstar. They already had Mo Vaughn, so I guess what they needed was a new superstar.

Nomar showed up in 1997 took shortstop from incumbent John Valentin and didn’t stop hitting or fidgeting with his batting gloves—a tic that every Little Leaguer in New England immediately copied. That season Nomar crushed everything that came his way: fastballs, curves, sliders, knuckle balls, it didn’t matter. Nomar tattooed the wall like Wade Boggs in his prime.

A new generation of Sox fans loved him for it. He wasn’t Nomar, he was NOMMAHHHHHHHH. He won the Rookie of the Year and played every game with the biggest smile. I remember the last game of his rookie year he stayed around after the game and signed autographs for what seemed like days.

Nomar loved Boston and Boston loved Nomar. It was a match made in baseball heaven.

The next year, Nomar hit more than he did his rookie year. By 2000 he led the league with .372

average which was the highest average by a right handed hitter since Joe DiMaggio. As it often happens with athletes and this town, the love affair between Boston and Nomar was starting to lose some of its shine. The fans still loved him but the press was beginning to turn on him a little bit. And when he showed up shirtless and yoked on the cover of Sports Illustrated, whispers of steroids started to spread.

To make matters worse Nomar’s first name was starting to change to “the oft-injured” Nomar Garciaparra. And with the additions of brand new superstar players like Pedro Martinez, Manny Ramirez, Johnny Damon and David Ortiz; someone was moving down in the pecking order of stars.

It all came to a head in the winter of 2003 when GM Theo Epstein had a deal to send Manny and Jon Lester (a throw in) to the Texas Rangers for Alex Rodriguez. Then the Red Sox were going to ship Nomar to the White Sox for Magglio Ordonez. But the complicated transaction didn’t pan out. To make matters worse teammate Kevin Millar went on SportsCenter and told the whole world that he’d rather ARod at short.

Yipes.

Things were awkward that spring and into summer as Nomar played but there seemed to be a dark cloud over shortstop. At the trading deadline, Epstein finally ripped off the Band-Aid and sent Nomar to the other Chicago team, the Cubs.

As you know, the Sox won the Series that year but Nomar was watching that him with his wife Mia Hamm. No one seemed to miss him.

Obviously, it’s awesome that the Sox won that year. I wouldn’t change any part of that drama for anything but it was a little sad that Nomar wasn’t there. He got a ring, but I’m sure it’s a hollow bauble.

In the late 90s Nomar gave us all something to cheer. It was the Golden Age of shortstops and while ARod was the best overall, Miguel Tejada won the MVPs, Edgar Renteria and Omar Vizquel won Gold Gloves and Derek Jeter had World Series trophies, no one hitter harder than Nomar (and I’m including ARod).

The skinny kid from Georgia Tech was amazing. And he looked like he was having so much fun too. Baseball is a lot like life, it can just wear you down after awhile. The glee and joy you find in your job or everyday life can evaporate in a second, if you’re not careful.

That’s why when you have that happiness you need to hold on to it as long as you can. Really drink it in. When I think of Nomar I choose to think of him as a pup slamming balls all over the park and signing autographs after.

I’m sure that’s the way he’d prefer to be remembered too; young and with a smile.