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The Best Bets in Boston Sports History

The Best Bets in Boston Sports History article feature image

Doug Pensinger/Getty Images. Pictured: The Red Sox celebrate winning the 2004 American League Championship Series.

‘Tis officially the season of “Best ______ in ______ History” content and you’d better believe I’m not letting it pass me by.

And since I don’t know anything about anything except — and perhaps including, as you might conclude from reading this — Boston sports and betting, here we are.

The best bets in Boston sports history.

First, a few rules.

The bet had to be “common enough” in the market (as decided by me), which means live betting presents a bit of a gray area. A live bet of the Red Sox down 5-0 in the bottom of the ninth against the Orioles on Mother’s Day, for example, is too obscure. A live bet in the middle of the Super Bowl, however … well you can scroll down a bit to find the ruling on that.

It also had to bet in favor of the Boston side. I’ll leave the list of most embarrassing Patriots losses in the past 20 years to someone else.

I also ruled out any bets on individual awards. I just didn’t feel like leading the list with Rick Porcello winning the Cy Young Award at 200-1. If you took that in the 2016 preseason consider this your shoutout.

And lastly, it had to be a bet for which I could track down the odds, or, at the very least, make a decent estimate using related odds. That may skew some recency into this list, I know (I’ll also hesitantly admit I’m 24. I was six when Tom Brady took over for Drew Bledsoe), so I’ll gladly accept late nominations for some 20th-century longshot wagers that I will undoubtedly miss.

If you’d prefer to just eviscerate me on Twitter, that works too.

But please, keep reading. I mean look, if you scroll past the first two bets you’ll find one from 1993!

10. 2017: Boston College vs. No. 1 Duke (CBB)

  • Spread: +15
  • Moneyline: 10-1

I really wanted to make a case for the first spot on this list to go to the 1994 upset of No. 1 North Carolina in the NCAA Tournament. But unfortunately, though the moment was bigger, the bet wasn’t. The Eagles were just 8-point underdogs in that game, implying a moneyline price more like 4-1.

In their 2017 upset of Duke (featuring Grayson Allen, Marvin Bagley III and Wendell Carter Jr.), however, they rewarded their moneyline backers with a payout of 10-1.

Top-ranked Duke had gone unscathed through its first 10 games, knocking off both No. 2 Michigan State and No. 7 Florida in the process. A noon start at Conte Forum seemed like an easy enough way to open ACC play and keep its perfect record intact, and oddsmakers agreed, giving Duke a 15-point edge in the betting market.

BC hung around early, though, and each time Duke opened up a multi-possession lead (18-12, 20-15, 26-22) the Eagles immediately closed it. They even ended the half on an 8-2 run to take a 48-41 lead into the break.

Duke, as was expected, came back in the second, and with less than three minutes to play, was up 79-75. A valiant effort looked to be all we’d get from BC.

But once again, the Eagles didn’t let a small lead grow, and with a 7-0 run were up three, and were able to close out a shocking 89-85 win.

9. 2017: Patriots to Come Back in Super Bowl 51

  • Live odds (multiple times): 16-1

You might’ve been expecting to see this one ranked a bit higher than ninth. But to be honest, even the No. 9 spot seems too generous to me, as will be made clear.

As I’m sure was the case — or at least a similar one — for many of you, I stepped out of my Super Bowl party at halftime to regroup and put on a different shirt before returning for the second half. I hadn’t thrown in the towel just yet, but I’d be lying if I said a live bet on a comeback ever realistically came close to crossing my mind.

Of course, as I’m sure was also the case for many of you, I was almost immediately (read: at noon the next day) looking up what sort of odds I’d have gotten had I done so.

16-1? At its peak? I mean, come on.

Ezra Shaw/Getty Images. Pictured: Julian Edelman

If you want to tell me that the Patriots didn’t actually have a 0.3% chance to win the game — as was calculated by ESPN Stats & Info — I’ll believe that. But even at, say, a 2% chance, fair odds would’ve been up near 50-1 (not that I’d expect that to be listed either — I doubt bettors were clamoring for live Falcons action at minus-a-house).

Something around 30-1 for the Patriots, though, and you’d find this bet in the top five. Remember, I’m doing my best to rank bets, not moments.

Now, someone (who sounds like a very smart man and terrific boss) once said that “the right side is the winning side.” In other words, I should basically shut my trap about how outrageous those odds were because the Patriots did win, and the sportsbooks did have to pay out all the New England believers.

All I’ll say is this: the next time your team is down 28-9 with two minutes left in the third and your opponent has the ball at your 41-yard line, find me if you want to make a live bet at 16-1.

8. 1993: Boston College vs. No. 1 Notre Dame (CFB)

  • Spread: +15 to +18
  • Estimated moneyline: 10-1

1993 was shaping up to be Notre Dame’s year.

The Irish moved into the No. 2 spot into the country in Week 8, and held the position behind Florida State until the two met in Week 12, where Notre Dame prevailed, 31-24, and took over the No. 1 ranking at 10-0 … with just one game to go.

You probably can sense where I’m going if you aren’t already familiar.

Mitchell Layton/Getty Images. Pictured: Tom Coughlin

At No. 17 in the country, Boston College — led by Tom Coughlin — was by no means a laughingstock, but as an underdog reportedly of 15 to 18 points, the Eagles weren’t given much of a chance. There was just no way Notre Dame would give up its title-game spot on the last day of the regular season, one week after taking out the nation’s top team.

For most of the game, though, BC was in control. The Eagles scored the first 10 points of the game and led 24-10 at halftime. They opened the second half with another touchdown, and gave up just a field goal in the third quarter to take a 31-17 lead into the fourth quarter. Then they added another seven to go up 38-17.

But the Fighting Irish stayed true to their name, and scored 22 unanswered points in the final 11 minutes to go up 39-38. The title run was back on, and a magical chapter seemed to have been added.

But, since you’re reading about the best bets in Boston history, that’s obviously not going to be the case.

BC quarterback Glenn Foley marched from the Eagles 25- to the Irish 24-yard line in a matter of a minute, setting up a 41-yard field goal attempt with five seconds to play. Kicker David Gordon hit it, and what would have gone down as one of the great comebacks in college football history — especially should Notre Dame have gone on to a national championship — was crushed.

7. 2017: Celtics vs. Cavaliers, Eastern Conference Finals Game 3

  • Spread: +15.5
  • Moneyline: 17-1

Not only were the Celtics outscored 247-190 in two consecutive games on their home floor to open this series, they also lost Isaiah Thomas in Game 2 to a hip injury — one from which he would not return, neither to the series nor the Celtics.

Let me refresh your memory as to the starting five the Celtics were working with from that point forth:

  • Avery Bradley
  • Marcus Smart
  • Jae Crowder
  • Al Horford
  • Amir Johnson


  • Kyrie Irving
  • J.R. Smith
  • LeBron James
  • Kevin Love
  • Tristan Thompson

Accounting for the injury, the back-to-back blowout losses and the switch to Cleveland’s home court, the Celtics entered Game 3 as 15.5-point underdogs. Only twice since 2005 (and perhaps further) has there been a bigger spread underdog in an NBA playoff game, both coming by way of the Grizzlies in a 2016 first-round series with the Spurs.

Memphis also lost both matchups handedly, failing to cover either spread.

This game looked to be heading that direction as well, with Boston going into halftime down 66-50. A 32-21 third quarter, however, brought the Celtics within five, and turned the final 12 minutes into a dogfight.

Nathaniel S. Butler/NBAE via Getty Images. Pictured: Avery Bradley

With seven minutes to go, the Celtics got to within one, and from that point on neither team saw a lead of greater than three points.

And after the Celtics allowed a Kyrie Irving layup to knot the game at 108 with 10 seconds to go, overtime was in the cards barring a score on their final possession — a score they’d get via an Avery Bradley three that hit the rim five times before dropping with a tenth of a tick to go.

It would be the Celtics’ only win in a series that lasted five games, but at 17-1, that bet alone was enough to profit 13 units for anyone blindly betting the C’s on a nightly basis.

6. 2013: Red Sox to Win World Series

  • Preseason odds: 28-1

Over the four-year span from 2012 to 2015, the Red Sox came in last place three times … and won a World Series.

In a disastrous 2012 season behind Bobby Valentine, they failed to reach the 70-win mark for the first time since 1981, and entered the offseason at 40-1 to win the World Series before making a few acquisitions.

They brought in Shane Victorino, Mike Napoli, Johnny Gomes, Koji Uehara and, of course, ditched Valentine for John Farrell, all of which led to an increase from 69 wins to 97 (the +17.3% increase is tied for the 24th highest in MLB history).

By the time they reached the Fall Classic they were -140 favorites, and ultimately cashed tickets for any bettors willing to gamble on the rebound season.

They never saw a postseason elimination game, winning their three series in four, six and six games, respectively. They did, however, face a near 2-0 deficit in the ALCS to the Tigers before a David Ortiz grand slam tied Game 2 at 5 in the bottom of the eighth.

Ortiz would go a ridiculous 11-for-16 (.688) in the World Series — the second-best mark of all time — en route to winning MVP of the series.

5. 1985-86: Patriots to Win AFC

  • Estimated odds entering playoffs: 30-1 to 40-1

Not a whole lot was expected of the Patriots entering the ’85 season. Having never won a playoff game since the merger (1970), they were given 30-1 odds to win the Super Bowl.

Somewhat impressively, those odds actually became longer (50-1) after the Pats had clinched a playoff spot. Perhaps that’s because they’d be playing in the Wild Card round, and would be road underdogs in each of their three games leading up to the Super Bowl should they make it that far.

As for the results in those three games:

  • at NY Jets (NE +3, estimated +133 moneyline): W, 26-14
  • at LA Raders (NE +6, estimated +216) W, 27-20
  • at Miami (NE +10.5, estimated +511) W, 31-14
Gin Ellis/Getty Images.

A moneyline rollover parlay at those prices would result in a payout around 44-1, but that was also the toughest possible path for New England, meaning a future bet probably would’ve been listed a bit lower, hence the estimate.

4. 2009: Boston College vs. No. 1 North Carolina (CBB)

  • Spread: +23
  • Moneyline: 33-1

There’s no real dramatic backstory to set this one up. No one’s making documentaries to celebrate a January regular season upset (though it probably found its way onto the UNC doc to highlight what little adversity the Heels overcame en route to their national championship three months later).

The 33-1 pregame moneyline price, however, makes this the biggest single-game upset in recent Boston sports history.

Led by six future NBA draftees — this was the Tyler Hansbrough-Ty Lawson-Wayne Ellington-Danny Green year — UNC was given the preseason No. 1 ranking. And behind a 13-0 start, the Heels showed no signs of giving it up, and certainly weren’t expecting to following a home game against a BC team with two losses to its name.

But the Eagles prevailed, 85-78, and were even rewarded with the No. 17 ranking following the game, which lasted until … the next game.

BC would lose to Harvard (by 12) three days later, and then go on to lose another three in a row.

But for anyone who cashed on the upset in Chapel Hill, it probably didn’t make a whole lot of difference.

3. 2001-02: Patriots to Win Super Bowl 36

  • Preseason betting odds: 60-1
  • Week 3 (Brady’s first start) betting odds: 100-1
  • Game moneyline: 7-1

Before we knew anything about being upset in a Super Bowl, we were the upsetters. And whether you had the Patriots as a preseason future bet or on the pregame moneyline, you walked away from Super Bowl 36 with a nice chunk of change in your pocket.

We’ve still yet to see a team with preseason odds of 60-1 or longer go on to win the Super Bowl since the 2001-02 Pats (though the Rams did win Super Bowl 34 at odds of 150-1 just two years prior).

We’ve also yet to see a Super Bowl favorite of 14 or more points lose a game (or even a 14-point spread, for that matter) since. The Pats closed at -12.5 in their Super Bowl 42 loss to the Giants.

Jim Davis/The Boston Globe via Getty Images. Pictured: Tom Brady

As for the “better” bet, you could make strong cases for both, though I’d side with the pregame moneyline. The main reason being that preseason bettors weren’t really betting on the true underdog story that came to be.

No one was taking the 60-1 bet with the hopes of Tom Brady taking over the starting job and leading the Patriots to a championship season (for anyone, if there is anyone, who bet took out a Pats future immediately following Bledsoe’s injury, you obviously take the cake here).

Plus, the 60-1 preseason odds imply a 1.64% probability, which is relatively closer to the random chance of one team out of 31 winning (3.23%), than the implied probability of 7-1 odds (12.5%) is to one team at random out of two (50%).

In other words, a 60-1 preseason bet can always be passed off as a “what the hell” gamble. A 7-1 Super Bowl underdog bet — at the time, at least — was more likely met with a, “what the hell are you thinking?”

2. 2004: Red Sox, Down 3-0 in ALCS, to Win World Series

  • Odds entering ALCS Game 4: 120-1

Someone’s going to need to explain to me how the Red Sox’ 120-1 odds to win the World Series when they were down 3-0 in the ALCS came about.

Even if every remaining ALCS game, as well as the series price in the World Series, were a toss-up (+100), the chance of all five outcomes occurring would be 1 in 32 (2^5).

Fair odds, therefore, which are generally better than what’s offered (books are, after all, trying to make money), would be +3100. And that’s not even accounting for the fact that the Red Sox were favored in three of their four ALCS wins, and -145 favorites in the World Series.

I suppose when you factor in that no team had ever come back from down 3-0, that it was one day removed from a 19-8 slaughtering, one year removed from the Aaron Boone home run, the seventh straight year of Yankee dominance in the AL East, 26 years after a home run by someone named Dent in a game that my dad and every other Bostonian born before 1960 claims to have been at, and the rest of an agonizing list that lasts another 86 years …

… you somehow end up at 120-1.

And those odds technically are the best of any bet on this list. But given that the driving force was the ALCS comeback (take a -145 leg out of a 120-1 five-leg parlay and you end up around 70-1), I’m slotting it in the 2-hole.

1. 1967: Red Sox to Win the Pennant

  • Preseason betting odds: 100-1

Did I list The Impossible Dream first just to try to win back some respect from all you — how do I put this — “more experienced” readers who think my previous choices are all too recent? Yes, I did.

But do I also think it’s clearly the deserved holder of the best-bet-in-Boston-sports-history title? Yes, I do.

The Red Sox finished ninth (out of 10) in the American League in 1966. It was their second straight ninth-place finish and third straight season of 90+ losses (including 100 in 1965). They hadn’t seen a winning season since 1958.

Okay, so it’s a last-to-first story … nothing we haven’t heard before (see No. 6). What makes this preseason bet such a ridiculous one, though, is the lack of the modern playoff system that’s now in place.

This wasn’t an “anything can happen if we make the playoffs” bet. It was a “we’re going to have the best record in the American League” bet.

Just an outrageous claim.

But, of course, they did. Behind both a first-time MVP (Carl Yastrzemski) and Cy Young Award winner (Jim Lonborg), they leapfrogged eight teams to take the pennant by one game over both Minnesota and Detroit in a season that included a final-weekend must-sweep two-game series with the Twins, who had previously been holding first place by a game.

A $10,000 payday for any bettors who were told they were burning a hundred bucks prior to the season. And, as Longborg estimates (to incentivize his teammates before the final game) below, that same amount in a salary bonus for each member of the Sox roster.

B Bennett/Getty Images. Pictured: Jim Lonborg

(The bonus actually turned out to be just north of $5K, but what kind of ending is that?)

Unlinked odds taken via Bet Labs and the archives of

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