The best and worst of Boston jerseys   

Updated: February 24, 2009, 3:22 AM ET

  • Comment
  • Email
  • Print
  • Share

We've covered Pittsburgh and L.A., and now, after going through the cyber-mountain of e-mails sent by New England-based listeners of the podcast, it's time to focus on arguably the most perpetually compelling sports town in America.

Before we begin, remember: This is not simply a ranking of Boston's greatest legends, although the player's on-field deeds figure prominently into the calculation. Other considerations include the aesthetic quality of the uniform's color scheme and individual number choice; the era the jersey evokes for local fans; and -- maybe most importantly -- how that player's style, attitude and success personify the history of Boston sports. In other words, decisions were dictated as much by the heart and gut as the brain.

Bill Simmons and Kevin Hench join Dave to discuss the Best and Worst Jerseys for a Boston Fan to wear.

Boston's teams have an unrivaled Dickensian quality. Yeah, Hub fans have been treated to a bounty of glorious moments (especially since Y2K), but their teams also seem paradoxically star-crossed. You might have heard before that the Red Sox traded a guy named Ruth, which ushered in a cursed century at the Fens. The Celtics of the '80s were one of the best NBA teams ever, but ultimately were overshadowed by Magic's Lakers (at least in terms of rings), and the deaths of two players who might otherwise have extended the dynasty into the '90s. The Patriots have won three Super Bowls in the 21st century, but they came up short (against a New York team, no less) in their bid to go undefeated. And let's not forget about that golf pro in Hawaii who helped stir up some trouble with his video camera.

Then there are the Boston Bruins, who won a couple of Stanley Cups in the early '70s, but left the locals wondering what might have been. Why? Because along with Phil Esposito, Johnny Bucyk, Ken Hodge and Gerry Cheevers, the Bs featured the man who holds the top spot on our list …

The Best Jersey For A Boston Sports Fan To Wear

1. Bobby Orr's Black Bruins No. 4
Of all the legendary names to have played in the Hub, no one better personifies the aforementioned yin and yang of the local sports scene. Orr is among a handful of the very best to ever lace up the skates, and is certainly the greatest defenseman in NHL history. Think about that: Can you name the all-time best NBA center, NFL QB, or major league pitcher without its leading to a debate? As exceptional as his stats were, though, Orr transcended numbers. It's one thing to say a player revolutionized his position in a sport; Orr's end-to-end rushes and highlight-reel goals were so singularly spectacular that no defenseman has ever remotely replicated them. Even though he played before the days of "SportsCenter," you can find some video montages on the Internet that tell the tale better than I could.

With all that said, there could have been so much more. Orr's 1971 team was the best in puck, but it was upset in the playoffs by the hated Bleu, Blanc et Rouge de Montreal. Even more damaging were those knees that slowed and ultimately ended his career, but not before he ditched Boston for Chicago in a move still shrouded in controversy.

Bottom line, if you're looking to represent both the highs and lows of being a Boston sports fan, Orr's black jersey (chosen because it's the one he was wearing when his overtime goal against the Blues in the '70 finals clinched the Bruins' first Cup in three decades) is the one you want. Especially if you can figure out how to suspend your body horizontally.

2. Larry Bird's green Celtics warmup jersey
Tough to choose which Celtic jersey should come first; dynasties, Hall of Famers, and legendary moments abound. It comes down, though, to Bill Russell and Bird, and Larry Legend wins the coin flip. Sure, that No. 33 on the simple, classic Celtics uni is a gem, but we're going with the warmup. Has there ever been a cooler, more intimidating move than when Bird didn't even take off his warmup jersey in the '88 Three-Point Shootout? Actually, yeah, there was, at the same event, as a matter of fact. When Bird walked off the court with his index finger extended to the sky before the money ball had even swished through to give him the win.

He also had one of the all-time "Formerly Great Lines That Would Now Be Considered Offensive in the Politically Correct 21st Century" when he said, "The one thing that always bothered me when I played in the NBA was I really got irritated when they put a white guy on me. I still don't understand why. A white guy would come out and I would always ask him: 'What, do you have a problem with your coach? Did your coach do this to you?'"

Another interesting Celtics candidate is Tommy Heinsohn, for reasons laid out by listener Jon Stark: "He's been a part of the organization for all 17 Celtics championships in one way or another, and in true Boston fashion, may be the single most biased announcer, if not human being, in television history. He really is a cult hero."

3. Fred Lynn/Gabe Kapler/Josh Beckett's home Red Sox No. 19
One of the best things about a sports town like Boston is that the diehard loyalty of the fans is passed down through the generations, and in the Red Sox clubhouse, so are the jersey numbers. Especially in these troubled economic times, it's nice when a fan can find a two-for-one deal. Fortunately, the Red Sox haven't tampered (much) with their handsome home white jerseys, right down to keeping the names off the backs, allowing the thrifty Fens fan to salute multiple eras with a single jersey.

As for specifics … you could go with No. 24 and represent Dewey Evans and Manny, but after the latter's shameful departure last season, do you really want to?

Then there's No. 31. As listener Mike Klein mentions, "With just that one jersey, you'd be honoring Jon Lester, who beat cancer, won a clinching World Series game, and threw a no-hitter all before age 25 and Dave Roberts, who stole second base in Game 4 of the 2004 ALCS." Fine points, Mike, but some might been sent into twitchy convulsions at the sight of the number also worn by this guy.

No. 47 is a good one, too, considering it's shown up on the back of would-be '86 Series hero Bruce Hurst, Jason Varitek (before he switched to No. 33), and the man at the helm when the Curse was broken in '04, Terry Francona. Trouble is, the number itself lacks a certain panache, no?

No argument if you opt for No. 25, with Tony C, Don Baylor and Mike Lowell all having taken turns in that number. Same goes for No. 40. It was worn by Hawk Harrelson during the '67 "Impossible Dream"; Carlton Fisk during his '69 call-up; then by Dewey Evans for a couple seasons; and Hendu had it on when he went deep in Game 5 of the '86 ALCS.

We settled on No. 19 because of Freddy Lynn's dynamic stretch in Boston, including his '75 two-fer of AL MVP and Rookie of the Year (although definitely in the classic jersey over the buttonless v-neck of the mid-to-late '70s); Gabe Kapler's wild popularity with Sox fans and cougars alike; and Josh Beckett's dominance in the '07 postseason. What really put No. 19 ahead of the other candidates, though, was the fact that, even before arriving in Boston, the then-Marlin Beckett single-armedly kept the Yankees from winning the '03 Series. Now that's loyalty.

4. Tom Brady's Red Patriots No. 12
Some will suggest that we go with Bill Belichick's inexplicable cutoff hoodie, but I'm a man of style. And while the Back Bay's swooning 14-year-old girls are busy fighting it out for the fashion mag cover-boy QB's dark blue No. 12, we've chosen the marvelous red jersey of the Pat Patriot Era. Why'd they ever get rid of those glorious getups? And for what, this two-toned mess?

Feh. Alright, so they've since tweaked 'em from that to this, but Pat Patriot still needs to drop the gloves with the Flying Elvis and do what Milan Lucic did to Mike Komisarek earlier this season.

As for the selection of Brady as our highest-ranked Pats jersey, is there really even a debate? Lots of sentiment for Andre Tippett, Steve Grogan, Stanley Morgan, Tedy Bruschi and others, but c'mon … I know Brady is a little too obvious, but he's somehow been able to stay universally likable through the Tuck Rule, the videotape scandal and the casting off of women that most of us would kill for (but that's coming from a guy who's partial to Moynihan over Bunchen). Question is, will that knee have Pats fans wondering what might have been? Guess we'll find out in about six months.

5. Mark Henderson's Red One-Piece Snowsuit
When the snowflakes start falling in Gillette Stadium, no true Patriots fan should be without a red snowsuit like the one worn back in December of '82 by Henderson, who, on work release from the pokey, steered his plow over a piece of snow-covered turf to clear space for a John Smith field goal in the 3-0 Pats win over a cranky Don Shula and his Dolphins.

6. Doug Flutie's White B.C. Eagles No. 22
Take it away, Brent Musburger … "Flutie flushed. Throws it down. Caught by Boston College! I don't believe it! It's a touchdown! The Eagles win it!"

7. Derek Sanderson's White Bruins No. 16
Sanderson's the guy who passed to Orr to make "the shot." Derek gets props for notoriously saying his pregame meal is "a steak and a blonde," and a few more props for being the analyst on NESN who would have Keys To The Game like "score goals." And if you want to go the extra mile, go 'head and grow the Fu Manchu.

Bonus: For the Southie Tough Guy Fan:
Danny Ainge's No. 44 for taking on and getting bitten by 7-foot-1 Tree Rollins; and Pedro Martinez's No. 45 for successfully dodging a hard-charging geriatric bull named Zim: Irving Fryar's No. 80 for punching out his own teammate, Hart Lee Dykes, in a bar fight.)

For the fan who tips his cap to tradition: Ted Williams' home Red Sox No. 9
I know, I know … not many people reading this even saw him play. Why not go with Yaz, Jim Rice, Manny Ramirez or even Mike Greenwell, all of whom played more recently in front of the Green Monster? Because the guy who first made "Boston Red Sox leftfielder" one of the most iconic positions in sports was Teddy Ballgame (underrated nickname, by the way). As with Orr, though, you can't think about Williams' career without wondering what might have been. His numbers rank among the best in history, but would've been even better had it not been for those two military stints. Then again, piloting combat missions in a war is pretty good for your street cred, too. This man was employed in two of the three coolest jobs in the world: big league ballplayer and combat pilot (the third being international spy). This was a man's man … "a real-life John Wayne," as Bob Costas called him. So cowboy up and tip your hat to the Greatest Hitter Who Ever Lived by throwing that No. 9 on your back. But please, no spitting.

For the XXX-Large Fan: Rich "El Guapo" Garces home Red Sox No. 34
Terry Forster became a celebrity after Letterman called him "a fat tub of goo," but I'm partial to the more ironic nickname "El Guapo" (translation: "The Handsome One"). As an added benefit, those nameless home white unis allow others to think you're showing support for another plus-sized No. 34 Sawk, Big Papi.

For the Dustin Pedroia-sized fan: Tony Franklin's Red Patriots No. 1
This is what an NFL player looks like? At least back in the mid-'80s in Foxborough, the answer was "yes." Whatever happened to barefoot kicking, by the way? Who decided this absurdity was a good idea, especially for a guy like Franklin who was booting it in the cold New England air? People will say it's "because it gives the kicker a better feel." Great. The reason we human beings wear shoes and socks when it's frigid outside is so that we don't have to feel it … and nobody's asking us to go kick a frozen ball. Whatever. Here's to you, your potbelly, that receding hairline and those frostbitten toes, Tony Franklin.

The Sports Guy's Vote: Sam "Bam" Cunningham Red Patriots No. 39
Maybe a bit far out for my tastes, but I'll defer to a fan who grew up watching him. Cunningham's a good choice if only because as a USC freshman he played a key role in integrating Southern college football by running all over Bear Bryant's Tide. And as you'll hear on the attached podcast, you Simmons sycophants get a good tip on what to get your pal when Christmas rolls around.

Near-Miss: Raymond Bourque's White Bruins No. 77
He pulled off one of the most endearing Boston sports moments when he pulled off his No. 7 Bruins sweater and gave it to the retired Bs No. 7, Phil Esposito.

Unfortunately, though, he has to be left off the "Best" list for bringing the Stanley Cup he won with Colorado back to Boston. His intentions might have been good, but it was essentially rubbing loyal Bruins fans' noses in it. Sorry if you disagree, Bourque supporters, but you'll thank me down the line for preserving your dignity.

Best of the Rest

Any member of the 2004 Red Sox (except Byung-Hyun Kim)
Any member of the 1970-72 Bruins
Any member of '60s or '80s Celtics (except Greg Kite)
Any member of the 2001 Patriots
Pierce's No. 34 /Garnett's No. 5/Allen's No. 20
Reggie Lewis' No. 35
Gerard Phelan's No. 20
Steve Grogan's No. 14
Andre Tippett's No. 56
John Hannah's No. 73
Stanley Morgan's No. 86
Cam Neely's No. 8
Willie O'Ree's No. 22
Bernie Carbo's No. 1
Bill Lee's No. 37
Jim Lonborg/Sam Malone's No. 16

There's your yin. Now let's yang. There's a potential joke in there somewhere -- "everybody Wang (Eugene) Chung tonight"? -- but we've got too much work right now to figure it out.

The Worst Jerseys for a Boston Sports Fan to Wear

1. Johnny Damon's Pink Red Sox No. 18
There is no greater sin in the fan rulebook than this: If you didn't suffer through the lean years, then you don't get to celebrate the good times … especially in a place like Boston. In spite of the current halcyon days of the early 21st century, most Hub fans still have the emotional calluses from the "junior, junior sky hook," Bucky Dent and Grady Little (not to mention the real-life tragedies of Conigliaro, Bias, Lewis, Stingley and Travis Roy).

Here in 2009, after enduring 100 years' worth of pain and torment, true Red Sox fans are now fighting for tickets with those previously apathetic Bostonians who've decided it's fun to root for a winner. Universally, such people are called "band-wagoners" and "front-runners." In Fenway, they're known as the "Pink Hat Crowd." We've gone here with Johnny Damon's jersey for the obvious reason that he bailed on the Sox to go to the Yanks. I know, Cashman & Co. overpaid to get him, but Damon's cavalier attitude that jumping ship to the archrival is something only fans care about is unacceptable. Spare me the "it's a business" talk. Tell that to Jackie Robinson, who retired instead of playing for the hated Giants.

2. Roger Clemens' Road Red Sox No. 21
We all know what a fine human being he's been since leaving Boston (see: throwing a bat/spear at Mike Piazza; his ongoing steroid denials; announcing that he'd like to be inducted into the Hall of Fame as a Yankee), but even with the Sox, he had some magical moments. Like when he responded to Hank Aaron's comment that pitchers shouldn't win the MVP by saying, "I wish he were still playing. I'd probably crack his head open to show him how valuable I was." The Rocket = Class act.

If, by chance, you have a soft spot for Roger, maybe the fact that the No. 21 was also worn Mike Torrez, who gave up the three-run shot to Bucky Dent in the '78 playoffs, will prevent your putting on this jersey.

But let's get back to those '86 Sox. How 'bout …

3. Bob Stanley's Road Red Sox No. 46
Most in-the-know Sox fans understand that Bill Buckner has unfairly been tabbed as the goat for what went down in the bottom of the 10th. There's plenty of blame to go around, from John McNamara to Rich (it was a passed ball, not a wild pitch) Gedman, but on Mookie's grounder, it was Stanley the Steamer who never got over to cover first, which would have pulled Buckner from the play/gaffe entirely.

4. Rick Pitino's Suit
The Pitino Sandwich: two tasty slices of college-bred ("bread?") success with a foul green mess in between. If Larry Bird, the Chief or McHale did walk through that door, one thing's for sure: He wouldn't be caught dead wearing this suit.

5. Tony Eason's Red Patriots No. 11
An overwhelming number of letters from Boston fans demanded that "Champaign Tony" be included here … and it certainly seems deserved. In broad terms, he's known as one of the three signal-callers selected in the first round of the '83 draft who didn't wind up in the Hall of Fame (along with Todd Blackledge and Ken O'Brien; the other three, Elway, Marino and Jim Kelly, all did). The damning moment, though, came in Super Bowl XX when he became the only starting QB in the game's history to not complete a single pass. Sure, there was a drop or maybe even two that weren't his fault, but the circumstances around his departure from that game are what locals still remember. Some say he was pulled after John Hannah insisted Ray Berry make the move; others believe Eason asked out after feeling the heat from the 46 D. Either way, it was shameful. We've gone with the red jersey since it's the one he wore while wilting under the pressure before standing on the sidelines of the Superdome that January day.

Dishonorable mention goes to all the other pre-Pioli first-round busts like Kenneth Sims, Reggie "One-Yard" Dupard, Hart Lee Dykes, Eugene Chung, et al.

6. Eric Mangini's Patriots Jacket
Take it away, Bobby DeNiro as Jimmy Conway in "Goodfellas:" "Never rat on your friends and always keep your mouth shut."

7. Gold Alternate Bruins, Any Number
Parachute pants, acid-washed jeans, mock turtlenecks … all laughable fashion statements these days, but at least they had their day in the sun. Even if the sun burns for another for another billion years, this third sweater will never look good. For the record, we almost went with Joe Thornton's No. 19, if only because he switched away from his original number (the much-cooler-for-a-centerman No. 6) but his trade to the Sharks back in '05 actually seems to be paying dividends for the current Bs.

Page 2 editor (and Boston native) Mike Philbrick's vote: Dino Radja's Road Celtics No. 40
"The Celtics and ML Carr centered their offense around a guy whose only achievement was leading the league in unfiltered cigarettes for three straight years (sorry, Vlade, but he beat you fair and square)."

This brings up an interesting point: The Celts have retired 21 jersey numbers worn by their legends, but they might want to consider retiring some bad ones to avoid putting a pox on future players. I know they're running out of available numbers, but the putrid stench left on some jerseys might just be too tough to wash away.

Besides Radja, No. 40 was defiled by Travis Knight and Joe Forte; and No. 55 was shamed by Acie Earl, Dwayne Schintzius and Wally Szczerbiak; but it's No. 42 that takes the (rancid) cake, having had its luster forever stripped by Kedrick Brown, Joe Wolf and the man whose pre-practice ritual was rumored to include a couple of belts, Vin Baker.

Instead of raising those numbers to the rafters, it might make better sense to have a bonfire ceremony.

Not Even For The Nudist Fan: Zeke Mowatt/Robert Parryman/Michael Timpson's Birthday Suits
As apocalyptically bad as the 1-15 Patriots were on the field, these three players exposed the franchise to even greater humiliation with their collectively asinine harassment of journalist Lisa Olson in the locker room. Instead of condemning his highly paid trio of overly aggressive nudists, then-owner Victor Kiam inexplicably placed the blame on Olson. No doubt Pats fans would like to throw a towel, a robe or maybe even one of those ugly gold Bruins jersey over this ugly incident.

Near-Miss: Glenn Wesley's White Bruins No. 26
Among Garden regulars, he's remembered for creating one of the biggest "what-ifs" ever, as in: "What if Wesley hadn't shot the puck over the wide-open goal in the first overtime of Game 1 of the 1990 Stanley Cup Finals against the Oilers?" Mighty Edmonton ended up winning the series in five games, but had Wesley finished off the rally that night (the Bruins were down 2-0 at one point), who knows? That said, Wesley was very solid during his time with the Bs, and after he won a Cup with the Hurricanes, at least he didn't come back to show it off to thousands of Bostonians like another aforementioned defenseman.

Worst of the Rest:
Any member of the (1-15) 1990 Patriots
Carl Everett's No. 2
Grady Little's No. 3
Will Cordero's No. 12
Wade Boggs' No. 26
Eric Gagne's No. 83
Scott "Missin'" Sisson's No. 9
"One-Yard" Reggie Dupard's No. 21
Leonard Russell's No. 32
Andy Katzenmoyer's No. 59
Kenneth Sims' No. 77
Hart Lee Dykes' No. 88
Dominique Wilkins/Ricky Davis' No. 12
Michael Olowokandi's No. 41
Eric Montross' No. 0

And there you have it. No doubt you've taken issue with one, two or 78 of the above selections and/or omissions, so drop me a line and let me know the error of my ways. People in Pittsburgh and L.A. already have. As far as that goes, some Angelenos were especially upset about the lack of either Kobe or Shaq-Fu on the "Best Jerseys" list.

I think this note from "Edwin" sums it up the best:

"Are you kidding? No Kobe??? The man is arguably one of the top 5 players EVER! He is arguably the best pure scorer EVER (has absolutely zero weaknesses in his offensive game, everyone else has at least one) ! He OWNS LA right now. They chanted MVP for him in Boston and MSG. You didn't even give him an honorable mention in the 'Best of the Rest' section! Magic is No. 1 (deservedly so), but come on!!! Kobe's Sunday white No. 24 (the one that he scored 81 points in) should be mentioned somewhere (if not top 7 at least in 'best of the rest').

"On that note, Shaq's No. 34 should be mentioned to a lesser extent. 3 time finals MVP, is part of 'the greatest big man/little man combo ever' [his quote], arguably the most dominant player ever (after Wilt).

"The sad part is that you get paid for this.


Not to be a contrarian, Edwin, but I happen to really like that part about getting paid. Now, as for the issue you and so many others have raised, lemme explain my logic.

I wrote the LA jersey column before Kobe and Shaq declared themselves best of chums after winning co-MVP honors at the All-Star Game. If you'll remember, they were at each other's throats for the better part of this century, including just last summer when Shaq inquired about whether Kobe's palate enjoyed the flavor of his posterior. Lakers fans took sides on this rivalry a long time ago; therefore, if I had selected either guy, it would have upset half of those fans. Don't you see, Edwin? It's like "Alien vs. Predator": Whoever wins, we lose.

As time goes by, it seems probable that Shaq's departure from LA was his own doing, and over the past few years he has taken some shots at his former team. Seems, then, that Kobe should get the nod … except that he made a change for the worse by swapping the great No. 8 for No. 24. Which of those is the right choice: The one he was wearing when he won three titles, or the lame one he's been wearing on the way to zero titles?

But as the late, great Jerry Orbach said to Patrick Swayze at the end of "Dirty Dancing," "When I'm wrong, I say I'm wrong." Some acknowledgement of those three-peat Lakers is certainly due, so …

Upon Further Review
… let's set aside the divisive rivals and honor the jersey of a player all Lakers fans can embrace: Robert Horry's No. 5. "Big Shot Rob" earned that nickname by knocking down 3-pointers to win four playoff games in the waning seconds during the Lakers' title run. We've gone with the home gold because it's the one he wore for his most famous winner, the 3-ball to beat the Kings in Game 4 of the '02 Western Conference finals.

Happy, Edwin?

Dave Dameshek is the host of the "Dameshek on Demand" daily podcast, available on Page 2, L.A.'s and Pittsburgh's You can e-mail him at


You must be signed in to post a comment

Already have an account?