New England Patriots: Should Bill Belichick regret trading Jimmy Garoppolo to 49ers?

TAMPA, FL - OCTOBER 5: A backview of Quarterbacks Tom Brady #12 and Jimmy Garoppolo #10 of the New England Patriots as they enter the field for pre-game warm-ups before the game against the Tampa Bay Buccaneers at Raymond James Stadium on October 5, 2017 in Tampa, Florida. The Patriots defeated the Buccaneers 19-14. (Photo by Don Juan Moore/Getty Images)
TAMPA, FL - OCTOBER 5: A backview of Quarterbacks Tom Brady #12 and Jimmy Garoppolo #10 of the New England Patriots as they enter the field for pre-game warm-ups before the game against the Tampa Bay Buccaneers at Raymond James Stadium on October 5, 2017 in Tampa, Florida. The Patriots defeated the Buccaneers 19-14. (Photo by Don Juan Moore/Getty Images) /
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When the New England Patriots were unable to retain quarterback Tom Brady in 2020, it was easy to assume head coach Bill Belichick instantly regretted trading Jimmy Garoppolo to the San Francisco 49ers. Should there be regret, though?

Back in 2018, ESPN’s Seth Wickersham suggested the New England Patriots were heading towards a massive breakup.

The premise of that blockbuster report highlighted apparent friction between head coach Bill Belichick, quarterback Tom Brady and team owner Robert Kraft, much of it centered around the quarterback pegged to eventually replace Brady, Jimmy Garoppolo.

Fans know the facts: Belichick elected to trade Jimmy G to the San Francisco 49ers prior to the 2017 trade deadline in exchange for a second-round pick. Garoppolo was in a contract year, and Belichick’s initial explanation was the situation to keep Garoppolo a Patriot was no longer tenable.

Two years later, Brady is now gone, too, joining the Tampa Bay Buccaneers as a free agent paralleling additional talk from Wickersham highlighting the dissolution of the relationship between Brady, Belichick and the Patriots franchise.

And now, Belichick is left with less-than-desirable quarterbacking options on his roster: Jarrett Stidham, Brian Hoyer and Cody Kessler.

So this understandably prompts the question: Does Belichick regret trading Garoppolo?

The true answer is complex and varies somewhere between “perhaps” and “absolutely not.” The lack of an heir apparent to Brady and his legacy is something Belichick will have to absorb this season and perhaps beyond. There’s no getting around that, yet few teams and head coaches are prepared to fill a void left by a bona fide Hall of Famer, let alone the greatest quarterback of all time.

Garoppolo was going to be Belichick’s next and perhaps final stamp on his legacy in New England, putting the franchise into excellent hands following Brady’s inevitable departure, whenever that was to come.

But it ultimately came much later than anyone, including Belichick, could have anticipated. Brady, 42 years old, was supposed to succumb to the regression always associated with Father Time. He was supposed to retire years ago.

Keyword: supposed.

Yet Belichick is the epitome of a head coach who values the end over the means. Few put a priority on winning more than Belichick, right?

And all one needs to do to draw a conclusion here is look at the results after the 2017 trade of Garoppolo. The Patriots narrowly lost the Super Bowl the year Jimmy G was traded, winning it the following year despite Brady and the offense not needing to be the primary factor.

In that sense, Belichick shouldn’t care about the trade. Nor should he have any thoughts of “what could have been.” Winning a Super Bowl in the short-term wake of a blockbuster, franchise-altering trade justifies everything, even if it merely meant the status quo would remain just a little while longer.

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Even if it comes at the cost of an uncertain future with Brady no longer in the picture.