Kennedy’s failure to lay out a rationale for taking on Markey was symptomatic of a campaign that was too confident for too long — didn’t think the usual rules applied or that Markey had enough fight in him to fend off one of the party’s bright young stars. https://politi.co/2Z0PdLw 
Kennedy’s candidacy was designed around the idea that a vote for Kennedy was an investment in his seemingly limitless political future, while Markey was already on his way out the door.
https://www.politico.com/news/2020/09/02/joe-kennedy-senate-campaign-failed-408033
Kennedy advisers concede that the campaign should have gone negative earlier & defined the incumbent while his polling numbers were low. But the campaign also blamed the press & the left wing of the party for giving Markey a free pass to reinvent himself. https://www.politico.com/news/2020/09/02/joe-kennedy-senate-campaign-failed-408033
A couple of tough quotes:

"The Markey campaign did a masterful job convincing voters Ed is someone he is not," one Dem strategist said.

"This goes to show you that the left doesn't do their homework and they're easily won over by bright shiny objects," said a Kennedy ally.
The campaign was also caught flat-footed by Markey’s late attempts to do the unthinkable: Weaponize Kennedy's last name.
https://www.politico.com/news/2020/09/02/joe-kennedy-senate-campaign-failed-408033
Markey's risky attack proved effective at rallying his progressive base. Even Speaker DeLeo was photographed holding up a T-shirt that read "Tell Ya Fatha." The speaker apologized privately, saying he didn’t know what the shirt meant, per 5 sources. https://www.politico.com/news/2020/09/02/joe-kennedy-senate-campaign-failed-408033
Kennedy unleashed his famous family in full in the final weeks, but sources close to the campaign say it came too late. Kennedy's internal polls showed him losing traction weeks before the election.
https://www.politico.com/news/2020/09/02/joe-kennedy-senate-campaign-failed-408033
Kennedy had already lost his cash advantage over Markey months earlier after spending $2.4 million in television ads in the spring that failed to move the dial — many saw that as a critical mistake. https://www.politico.com/news/2020/09/02/joe-kennedy-senate-campaign-failed-408033
The symbolic blow came in East Boston, where the Kennedy family has its roots & the congressman launched his campaign.

He made an end-of-campaign speech there and sought to dismiss the idea that his motivation for running mattered at all.

Days later, he lost every precinct.
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