Could Retrocession to Maryland Solve D.C.'s Problem?

D.C. representative Oye Owolewa and Executive Director for Puerto Rico 51st George Laws Garcia join Chuck Todd for a deep dive into one of America’s most overlooked democratic debates — the fight for statehood for Washington, D.C. and Puerto Rico. With over 3 million Americans lacking full representation in Congress, Chuck explores the political, constitutional, and cultural hurdles standing in the way. From Puerto Rico’s 58% support for statehood to the District’s struggle under federal oversight, the episode unpacks how history, partisanship, and outdated systems continue to stall progress.

The conversation dives into whether D.C. and Puerto Rico would need to enter as a political “duo”, why half measures like expanded autonomy wouldn’t hold up, and how the economic and tax inequalities faced by both territories have real-world consequences. With bipartisan murmurs of support and the next generation of lawmakers pushing the issue, Chuck asks: is America finally ready to welcome its 51st — and maybe 52nd — states?

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Timeline:

(Timestamps may vary based on advertisements)

00:00 Rep. Oye Owolewa and George Laws Garcia join the Chuck ToddCast

02:00 Over 3 million Americans don’t have representation

04:15 The status of Puerto Rico’s fight for statehood

06:30 Public split in Puerto Rico over its status

08:45 DC can pass local laws governing DC and Puerto Rico

09:30 Puerto Rico’s residents have 58% support for statehood

11:45 Should DC be holding more referendums on this issue?

12:45 The importance of lobbying people in other states

14:15 Muriel Bowser has been boxed in by the administration

15:30 DC and neighboring states don’t want to integrate

16:30 Should Virgin Islands join the fight for statehood?

19:30 DC would be solidly Democratic, Puerto Rico is more up in the air

20:15 Would DC & Puerto Rico have to both get statehood at the same time?

22:00 A new constitutional amendment may need to be passed

23:00 States are only added as duos due to political considerations

24:00 The GOP won’t add DC as a state without a Republican counterpart

26:15 Puerto Rico’s politics would be a huge question mark if admitted

27:45 How would the four congressional seats in PR split politically?

29:15 Is there a middle ground that would grant rights without statehood?

31:30 Why half measures wouldn’t work, Congress could claw things back

33:00 Statehood admission much easier to pass than an amendment

35:30 There is some bipartisan support for statehood

38:00 Could the PR statehood push get a boost from NY and FL?

39:00 DC lost out on huge amounts of Covid money by not being a state

41:30 Puerto Rico receives massively unequal funding relative to states

44:15 Puerto Rico pays more in federal taxes than at least 3 states

46:15 Tax base in DC would be stronger with statehood

47:00 Business are hesitant to operate in DC without statehood status

49:00 Puerto Rico had a huge manufacturing base that has diminished

51:00 Statehood wouldn’t harm people living in other states

53:00 States were added in 19th century where English wasn’t primary language

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