25. Mike Greenwell
Man, I wanted Greenwell to continue that unbroken Sox left field MVP lineage of Willams, Yaz and Rice. If Canseco didn’t have a monster 1988, it’s probable that Greenwell would have been number four.
But he did (with better living through chemicals), Greenie fell short and ended up as the American League MVP bridesmaid. For ten seasons Greenwell wasn’t a perennial MVP candidate but he was really good. He hit for average, more than a little power and was a fun player to root for.
He wasn’t fast nor could he field the easiest position in the Majors (left field at Fenway) but you could do a lot worse with Greenwell hitting third in the lineup.
He played in Game Six (struck out on three straight pitches), often destroyed centerfield teammate Ellis Burks because he was a disaster in left and got his ass handed to him when he tried to big time Mo Vaughn in the batting cages when the Hit Dog was a rookie. However he was never boring. I like dudes with personality on the Sox.
Fun fact, I personally saw him hit an inside-the-park grand slam against the Yankees. How about that?
Speaking of better living through chemistry.
Am I a Roger Clemens fan today? No. I can’t say that I am. Do I hate him as much as I did 20 years ago? Also no. But 35+ years ago he was, without a doubt, my absolute favorite player in the world.
These caveats all count for something in the rankings.
We don’t have to go through Clemens’ career high/low lights: MVP and a billion Cy Young awards, two 20K games, a couple of World Series titles, HGH, an extramarital relationship with an underage girl, playing for the Yankees, inability to beat Dave Stewart or Pedro Martinez when it matters, his unique ability to completely psyche himself out on the mound on front of 40,000 people.
It’s all part of the Clemens stew that made Roger, Roger. I don’t know. Aside from 1986 when he came on like a rocket (pun intended), I can’t say that I enjoyed the Roger Clemens experience. I remember making more excuses for him during his Sox career than actually enjoying him pitch.
I guess that’s what you do when you’re young and have sports idols, isn’t it? The ump was obviously squeezing him, his Teenage Mutant Ninja Turtle shoelaces were too tight, the manager removed him from the game against his will, he was just too pumped up for this important game. It was always something.
Rooting for Roger Clemens was never easy as he mixed transcendent dominance with abject frustration and by the time he left I think everyone was just plain exhausted of the rocket ride. If he finished the twilight of his career in Toronto and Houston, I think we all would’ve been okay.
But he didn’t.
Add that to the pile of complexity that is Roger Clemens.
23. Nate Eovaldi
Can a journeyman who pitched one awesome game and lost be a favorite? He can if he’s Nate Eovaldi.
It was one of the most tense games I’ve ever fallen asleep to. I know that sounds crazy but it started at 8:00 pm and ended after 3:00 am.
Eovaldi was the loser in this game as he gave up a walk-off homer to LA third baseman Max Muncy but he saved the Sox pitching staff that night as he gutted through six (mostly shutout) innings.
The Red Sox went on to take the next two games and won the Series that year. Much like Tim Wakefield taking the bullet for the staff in Game Three of the 2004 ALCS, I don’t think the Sox beat LA without Eovaldi pitching his arm off in this game.
When we think of how we’d be as pro athletes, I think a lot of us would say “I'm a team player” and “I don’t care about my health as long as the team wins” but it’s bullshit. Most people don’t put team first because it’s hard to do that. And a lot of times if you do do that and you get hurt, you’re screwed.
So it’s nice when a player does that. And that’s what Nate Eovaldi did on that October 2018 night. For that he’ll always be one of my favorite players and I wish he was still with the club.
22. Andrew Benintendi
The outfield for the Red Sox in the late teens (Benintendi, Jackie Bradley Jr. and Mookie Betts) is my favorite outfield ever.
That’s what I like most about sports, but baseball in general. One of the reasons why you watch the seemingly endless parade of games is because it connects you to something in your past.
Whether it’s at Fenway Park or on the diamond at the Town Park in Amesbury, at its best, baseball is about the relationships you make with your teammates.
The three Bs had that strong bond, or at least it seemed like they did.
Benintendi came up last and had the most hype. He was a high draft pick from the University of Arkansas and he was the kid that might be the best. Mookie had the MVP, Jackie had the highlight reel of unbelievable catches, but Benintendi was going to be the one who outdid both of them.
Fun fact: I saw Benintendi’s first pro homer when he was a member of the Lowell Spinners. He turned on a fastball and launched it out of LeLacheur Park. It was crushed and I thought, this kid’s the real deal.
Unfortunately Benintendi was good (he made the All-Star team after the Sox traded him the Kansas City) and he had his moments (his defense in the 2018 postseason is iconic) but he never quite lived up to the hype.
He’s bounced around the league but by the end of his career there will be nothing to be ashamed of, but that potential of youth. That’s what I’ll remember most.
Again another connection for us all.
21. Don Baylor
One of these firsts were the first time a player who wasn’t homegrown had a great year for the Sox. That player was Baylor. I was used to players like Jim Rice, Dwight Evans, Wade Boggs, Roger Clemens, Rich Gedman, Bruce Hurst and Oil Can Boyd being good for the Sox. They came up through their system and (theoretically) you watched their careers unfold. Since this was my first year of following baseball, I knew that these guys were good because of course they’re good; that's how baseball works. .
But it wasn’t until this year that I fully understood that team actually acquire good players too. When I looked on the back of Baylor’s baseball card (he was pictured as a Yankee!) and saw his numbers, the amount of teams and that he was the 1979 MVP, I was shocked.
“Why wouldn’t you keep a guy like that forever? Why did the Orioles and A’s and Angels and Yankees let him go? He’s good!”
But at the same time, I thought it was awesome that he was good for the Sox. How did we get so lucky? Not only was he good on the field but supposedly he was a good guy in the clubhouse. The papers say he runs the team’s Kangaroo Court.
What the fuck is a Kangaroo Court? Why do they need this? Why don’t we have one of these on my Little League team? It sounded so cool.
Between the bombs, the frozen ropes he hit for doubles and being a Kangaroo Court judge—a role he played on a bunch of other clubs—Don Baylor was built like a brick shithouse and seemed exotic to me because of his well traveled resume. Plus he got hit by the pitch a lot. And it never looked like it hurt him. New guy, awesome guy, tough guy. So cool.
Like I said he produced too. In ALCS Game Five against his old team, it was Baylor who got the ninth inning started with a home run off Mike Witt in the top of the ninth.
Without that dinger, Dave Henderson is just another guy who made a mistake that lost Boston a big game. Baylor was a catalyst in more ways than one and made a lot of things happen in 1986–including a dropped foul pop up in Clemens’ 20K game. If he catches that, Clemens finishes with 19.
Every team should have a Don Baylor type. That's just smart baseball.
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