Taking on Markey might be Kennedy’s best option to ascend to the Senate

Joe Kennedy III. Jessica Rinaldi/Globe Staff/Globe Staff

It’s 2019, and one hard-and-fast rule of Massachusetts politics has officially been done away with: Incumbents can’t be challenged.

In the past, ambitious Democrats were supposed to wait for someone to resign or retire before they ran for their seat. But then Ayanna Pressley defeated 20-year incumbent Michael E. Capuano in the Seventh District, based in Boston, and now all bets are off. Nearly every member of Congress in Massachusetts is on track to face a primary next year — although some challengers are more serious than others.

No doubt Representative Joe Kennedy III would have benefited from the old status quo. An open seat would come up, the party would clear the field for Kennedy, and he would never be challenged again by another member of his party. But times have changed, and Kennedy appears to be rethinking his plans by flirting with his own primary challenge to Senator Edward J. Markey.

For Kennedy, it's a simple cost-vs.-benefit analysis of now vs. later — and taking on Markey might be his best option to ascend to the upper chamber in the near future. Markey is liked among Democrats, but polls show no proof that he’s deeply loved. The senator’s $4 million campaign bank account looks impressive, but Kennedy already has slightly more on hand. Markey is also a known quantity for Kennedy, who can make an argument for generational change.

The future, however, has a lot more question marks for Kennedy. If he passes on a Markey challenge, there are two ways he could run for the Senate in the coming years:

First, if Elizabeth Warren is elected president, there would be a special election in 2021. Kennedy would probably be the favorite, but there’s more risk for him in that scenario than in a 2020 challenge to Markey.

He has no idea who would also run in the Democratic primary. The last two special elections for the Senate brought out a number of candidates in the primary, thanks in part to the fact that candidates don’t have to give up their current seats to run.

Pressley, who will have served just a single full term, could go for it without giving up her current seat. (And would Katherine Clark, who is ascendant in House leadership, opt to do the same?)

But for the sake of argument, let’s hand Kennedy the nomination and consider instead how high-profile and delicious the general election would be for Republicans around the country.

It would be the first high-profile election under President Warren, and it would be in her home state of Massachusetts and featuring a Kennedy. The Republican candidate would have seemingly endless financial resources available to try to embarrass Warren and tarnish the Kennedy image, something that could linger even if Kennedy ultimately won.

But what if Warren is not elected president? Kennedy would need to wait five years and hope Warren doesn’t seek reelection in 2024. If she follows the path of most failed presidential candidates and stays in the Senate, then Kennedy would need to wait until Markey is up again in 2026 and hope he doesn’t run for reelection.

Consider what the Massachusetts political world could look like in 2024 or 2026. Has Attorney General Maura Healy been elected the state’s first woman governor? Or maybe Boston Mayor Martin J. Walsh is governor, and he’s looking for a Senate seat.

Also in 2024, Pressley will no longer be a House freshman, but a third-term incumbent. And she’s already proven she doesn’t shy away from primaries.

So, as shocked as many in Massachusetts political circles were this past weekend about the idea of Kennedy challenging Markey, maybe they should be more upset that they never thought of it before.