While David Ortiz continues to struggle at the plate, I’ll continue to say that I’d rather stand behind him and be wrong than abandon him and be right. Papi broke us out of bondage and led us to the Promised Land. If he’s going to wander in the wilderness a little bit, I for one am not going to be asking the boys in metal shop to make us a golden Matt Holliday. Papi’s done too much for us to lose faith now. Having said that, there’s no denying the last two months have been agonizing to watch. As Uncle Buck and I were saying the other day, Papi’s struggles have ranked right up there with some of the most painful episodes in Boston sports history. We’re not talking about quick moments of agony like Aaron Boone’s homer that go away quick like the pain from ripping off a BandAid. This is a list of the day-in-day-out sagas of pure misery where time stands still and you don’t think they’re ever going to end, like Ortiz’ power outage. Ranking the others:

10. Dead Williams

The 1999 All Star Game at Fenway was one of the purely great sports moments of our lifetimes. Ted Williams was the Lion in Winter. A heroic, iconic, beloved figure, embraced by old timers and current players alike. There was only one, minor, nagging, sour note: That ridiculous hitter.net hat his son John Henry Williams had him wear. What we didn’t know at the time was that the stupid hat was a harbinger of the grotesque things to come. John Henry did everything to exploit Ted short of organ harvesting and grandpa porn. And after his death, it got worse. John Henry had his dad turned into a Tedsicle in hopes of raking in some of that ultra-valuable 23rd century money. The stories of severed heads in cryofreeze were so macabre, the kid not only got ripped by Dom Dimaggio at Ted’s memorial service, but when John Henry himself died a short time later he was mourned by no one.
Watching it was as painful as… staring at the sun.

9. Jim Plunkett Thrown to the Wolves

Plunkett was the savior of the Patriots franchise when they were at their most desperate need of savior-ing. He was the Heisman winner out of Stanford when the Pats drafted him with the No. 1 overall pick in ‘71. Unfortunately, the Pats put Plunkett behind an offensive line with all the blocking of a parking lot speed bump and he became synonymous with everything that was wrong with the Patriots. Eventually they traded him to San Francisco in a deal that laid the foundation for the great Pats teams of the late 70s. But Plunkett was a good guy who deserved better as proven years later when he won two Super Bowls and in the process did the impossible: made people around here glad the Raiders won.
Watching it was as painful as… open eyes in a sandstorm.

8. Johnny Most Running Out the Clock

Johnny was 89 when he retired. Which is remarkable given that he died 3 years later at the age of 69. He only seemed 20 years older due to a debilitating nicotine habit. Toward the end he was almost unlistenable, given to massive, uncontrollable coughing fits where it sounded like his major organs were going to be raining down into the stands “from high above courtside.” It got so bad that for the first time ever they made him work with a sidekick who could jump in to do play-by-play during one of Most’s death spasms. The fact that the guy measuring Most for a coffin was a young, skinny kid named Glen Ordway didn’t make it any easier to listen to.
Watching Listening to it was as painful as… two pieces of styrofoam rubbing together

7. The Joe Kerrigan Era

Short lived though is was, the Major League managerial career of Joe Kerrigan was a complete, total and utter failure in all respects. Not everyone loved Jimy Williams, but a lot of people did. But exactly no one loved Dan Duquette, or his puppet Kerrigan. During the first workout after 9/11, when the whole country was still in a state of shock, Carl Everett marked the occasion by tailing Kerrigan from his office to the field screaming in his face that he was a racist. One of the most unlikeable Sox teams of all time (Where have you gone, Mike Lansing?) openly quit on him. And the memory of Kerrigan sending an obviously hurt Pedro Martinez out to pitch with 87 MPH stuff because management questioned whether he was really hurt is enough to make this list all by itself.
Watching it was as painful as… the Capt. Acevedo oral rape scene from Season 3 of “The Shield”

6. The Last Days of Pete Carroll

Everyone liked Pete Carroll as a guy. You heard it all the time. “Pete is a good guy…” followed by the sound of a knife plunging into his rib cage and turning. But most of the regicide was coming from within the Patriots organization. In 1999 the team started out 6-2. In the 2nd half of the season, they were 2-6. And there was no question about who was taking the brunt of the criticism. Terry Glenn went into open revolt. The team quit on him. Bobby Grier told everyone with a microphone that he’d given Carroll plenty of talent to win with and it was all Pete’s fault. Predictably that lifeboat gun battle sank both guys, but things have worked out slightly better for Carroll and the Pats than they have for Grier.
Watching it was as painful as… the Gene Hackman-Barbra Hersey kissing scene from “Hoosiers”

5. 1992-2008 Roger Clemens


In the 7 seasons prior to ‘92, Clemens won 17+ games every year and 3 Cy Young Awards. In his final four years with the Sox he went 40-39. Then he left the Sox, found unimaginable riches, Human Growth Hormone, 4 more Cys and that 10 MPH that was missing off his fastball. Only his post-career humiliation has taken the sting off the previous 16 years of watching him get his balls washed by the baseball world
Watching it was as painful as… your ex-girlfriend getting into shape after she dumps you.

4. The Border War When the Patriots Were Losing

It wasn’t enough that Bill Parcells extinguished the burning kindling of the Patriots dynasty before the fire could get going by leaving for the Jets. Or that he took the coaching staff, including a few named Belichick, Crennel and Weis with him. After a couple of years he put a poison pill in a free agent contract offer to Curtis Martin, forcing the Pats to say goodbye to the best Running Back in team history and one of the all time class guys ever in the NFL. The compensatory draft picks that became the ill-fated Robert Edwards and the forgotten Chris Floyd couldn’t ease the pain of watching Martin rack up yards while banging Toni Braxton.
Watching it was as painful as… Phish at Fenway

3. Post-heart Attack Reggie Lewis

Seeing Reggie Lewis’ career end at the age of 27 due to heart problems was sad. But at least you could hang your hat on the fact that he was alive and had his health and his whole life ahead of him. Until his wife went through the “Physicians” section of the Yellow Pages calling every doctor from Dr. A. Aaron to Dr. Z. Zyzzyx until she could get one to sign off on allowing Reggie to play ball again. To the surprise of no one save Donna Lewis and the quack she found, Reggie dropped dead on the court during practice that summer.
Watching it was as painful as… Clorox in the eyes

2. Larry Bird’s Back

A while ago I met a guy who works as a trainer for the Pacers who said he’s been working for Bird since his back started to act up… in the mid 80s. That means Bird played the last 8 years of his career at least with a back problem that got degeneratively worse with each game. By the end, when he wasn’t on the court, he had to lay on his stomach on the hardwood. The fact that he’d come in an be occasionally brilliant, like that same 1st round playoff game against the Hornets where Lewis first collapsed, made it more painful for what might have been.
Watching it was as painful as… the Kathy Bates nude scene in “About Schmidt.”

1. Bobby Orr, Blackhawk

Arguably the most beloved figure in the history of Boston sports, Orr should have died in a Bruins uniform at the age of 100. Only the worst betrayal since Judas kept that from happening. Orr’s agent Alan Eagleson made a lot more than 30 pieces of silver, which led to jail time, his expulsion from the Hockey Hall of Fame, and presumably a spot in the Inner Circle of Hell next to Judas. And for Bruins fans, the pictures of Orr in a ‘Hawks uniform might as well be a crucifix.
Watching it was as painful as… the scourging scene from “Passion of the Christ”