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I wouldn't start a paragraph with "He played..."; name the subject in a new paragraph
"Financial success gave him independence" this is ambiguous as written; without the second half of the sentence, it sounds like he's independent from his parents. Any way to clarify what "independence" was in this case without straying into OR?
AFAIK "Politico" is colloquial; how about the more usual "early political career" as a section title?
Can you clarify what Meehan means by "dead heads"? The best known use of the term is for these poeple...
"Meehan and Crossan reconciled," perhaps "Meehan and Crossan later reconciled,", for flow?
"bolting the party"; "bolting" is odd, here, to me. I'd suggest simply "leaving".
" leader of the 35th ward": "leader" is ambiguous; do you mean councilman?
"he tried for the": I'd prefer "ran" over "tried", given that this is an election.
"noting that" is too heavy a use of Wikipedia's voice, as it implies it was a fact. If we're providing inline attribution, I'd recommend "stated" or "said" or "wrote".
"allegations of insider corruption began to attach to Meehan's name" seems rather contorted. "Allegations of insider corruption were made about Meehan" or equivalent would be better.
Last sentence of "Sheriff" has two changes of direction; "nonetheless", then "but". Would flow better if broken up.
Resuming, "mounted another anti-corruption campaign" implies that it was a campaign against corruption, rather than an election campaign in which corruption was the major theme.
"100,000 vote majorities" implies multiple elections; which ones are you referring to?
"blasted" is verging on journalese.
Do we know why Meehan didn't run for a third term?
"Meehan backed the primary victors..." maybe clarify with "in the general election"?
"Harold Stassen, was selected..." in this case, the reverse; clarify that this is a primary.
"honored statewide by being named" why not simply "named"?
Spotchecked Madonna and McLarnon; I'm not seeing stuff about the 1951 election on page 62
That source also has a considerable amount of detail that it wouldn't hurt to add to the article. At 1300 words I think it meets my own arbitrary minimum for a GA, so I'm not going to fail it if you don't, but it's all there in a single place so it shouldn't be hard.
Some of the paraphrasing is a little too close for comfort. " quickly degenerated into a name-calling contest" in the source, "quickly degenerated into a name-calling contest" in the article. I'd suggest double-checking anything that isn't plain statement of fact. I can't check very many more sources; most require a subscription.
@Coemgenus: To be honest, I don't like "political boss" much, either; what does the term even mean? I think any meaning in it is entirely redundant to the final lead sentence. In the interests of getting this through quickly, I have simply trimmed that fragment, so that I can pass this. If you disagree, we can continue to discuss it, but I really think that based on what you have in the body, "influential member" and "unofficial head of the Republican party" is as far as you can go. Vanamonde (Talk)16:23, 19 September 2019 (UTC)Reply