Hart: The real ‘what-ifs’ in Boston sports history

Andy Hart
June 05, 2020 - 6:25 am

Thursday afternoon, the Dale & Keefe show on WEEI radio put together top-five lists of the greatest “what-ifs” in Boston sports history.

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As sports fans we are all aware of some of the greatest and most unfortunate moments from 100-plus years of New England sports successes, failures and legends. But what if a trade, free agent signing, injury or single play had gone differently? With the butterfly effect, what could have been?

In this current sports-free world that’s still controlled by the coronavirus pandemic, and prompted by the upcoming anniversary of Celtics No. 2 overall pick Len Bias’ death shortly after the draft from a cocaine overdose, the “what-if” list topic offered up on Dale & Keefe was both an intriguing and potentially overwhelming endeavor.

With all due respect to Rich Keefe and former Patriots tight end-turned-co-host Jermaine Wiggins, the lists that aired by the two talk radio mavens – which for their purposes didn’t include Bias -- were a bit too modern, too myopic.

While some of Keefe and Wiggins’ selections were pretty on point, others seemingly fell victim to relative recency bias from the last 20 years or just flat out were greatly overrated.

Given Boston’s rich history of success and star players, including the last two decades of consistent winning in all four major sports, we tend to forget that heartache was more commonplace in the not-so-distant past.

With that in mind, here’s another man’s swing at the idea of the top-five biggest “what-ifs” in Boston sports history. Love it. Hate it. Debate it.

What if…

1 – …Drew Bledsoe never got knocked out of action by Mo Lewis in 2001? – The simple answer? The greatest dynasty in NFL history would likely never have gotten off the ground. Bill Belichick, who was about to fall to 0-2 coming off a 5-11 season may have been on his way to being fired. Tom Brady remains a backup to the $100 million Bledsoe. Two Hall of Famers would have ended up as football history footnotes rather than GOATs. It’s crazy to think, but it is what it is.

2 – …Babe Ruth was never sold to the Yankees by money-needy Red Sox owner Harry Frazee in 1919? – The Sultan of Swat would never have built his house in New York while changing the game of baseball with his powerful swings. The Red Sox may not have gone 86 years between World Series titles. The Yankees probably wouldn’t have been the century-long dynasty that they ended up becoming. So many New England fans would have potentially had many fewer miserable summahs!

3 – …Len Bias didn’t die shortly after being taken No. 2 overall by the Celtics in the 1986 NBA Draft? – Though there is always a possibility that Bias wouldn’t have lived up to the hype, most likely the Maryland star would have taken the torch from Larry Bird leading the best team in basketball and kept the Celtics dynasty rolling through the late 80s and early 90s. Things may very well have turned out very differently for the Pistons and Bulls in the Eastern Conference and there probably wouldn’t have been quite as long a wait to add another banner to the Garden rafters.

4 – … Robert Kraft didn’t buy the Patriots, keeping them from moving to St. Louis to become the Stallions? – While the Bledsoe injury kick started the dynasty, if Kraft hadn’t kept the Patriots in New England the region might not have even had a football team. Or we’d be dealing with a replacement expansion team like they have for years in Houston and Cleveland. The Patriots rejuvenated Boston sports and the city’s championship run. They set a new bar in New England. Had they left town, there’s no telling how many – or few – titles we would have seen in Boston over the last couple decades. After staying put in Foxborough, the Patriots’ rising tide seemed to lift all of Boston’s pro sports championships.

5 – …The Red Sox had signed Jackie Robinson when they had him in Boston for a tryout in 1945? – Certainly adding a player of Robinson’s talent – to a team that already had Ted Williams – could have changed the course of the Red Sox fate on the field. But bringing a black player to Boston more than a decade before breaking the Sox color barrier with Pumpsie Green could have changed the organization’s and city’s reputation in race relations with ramifications that might be felt today. On and off the field Robinson could have changed so much for so many people, if only his tryout weren’t considered to have been little more than a “sham.”

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