With help from Kelly Garrity

PROGRESSIVE PROGRESS — Michelle Wu swept into the mayor’s office with big, progressive ideas for Boston and a mandate from voters to implement them. Eighteen months later, she’s running into roadblocks on several of her signature proposals.

But Wu isn’t pumping the brakes.

Wu’s effort to reinstitute and modernize rent control is facing resistance from real-estate leaders and state lawmakers. Her proposal to overhaul the city’s planning and development processes (by diluting the Boston Planning & Development Agency) faces a similarly uncertain future on Beacon Hill amid pushback from developers and a shaky economy.

She’s facing a(nother) lawsuit over her changes to outdoor dining in the North End. Two public safety unions are moving toward arbitration over contract negotiations they say have reached an impasse. And business leaders are “freaking out” that they no longer have a direct line to the mayor’s office.

But some political observers see the mounting pushback as Wu making progress on her goals, according to a weekend read from The New York Times’ Jenna Russell. And others tell Playbook that resistance is, frankly, normal.

“This is not college, where the person with the best grades gets [into the honor society] Phi Beta Kappa,” former Boston city councilor Larry DiCara said. “This is politics. And sometimes people with really good ideas don’t get them through.”

Boston mayors have historically struggled to push their agendas up Beacon Hill. Even Marty Walsh, a former state representative, couldn’t get his old colleagues on board with proposals like imposing a fee on high-dollar real-estate transactions.

But Wu is giving that one another go, at a time when the Boston Globe reports real-estate transfer taxes are seeing new life at the state level as Massachusetts’ housing woes deepen. Bids are also due next month for the first round of her program offering up 150 vacant lots to developers willing to build affordable housing on them.

And she appears to be making progress on another goal: reopening services on Long Island for people who are homeless and struggling with substance abuse.

Boston is “rounding the bend … on the last set of permits” to rebuild the bridge to Long Island and “reactivate” transportation there, Wu said on WCVB’s “On The Record” over the weekend. Wu was vague on details. And a spokesperson for Quincy Mayor Thomas Koch, who has for years battled Boston in court over reconstructing the bridge that touches both cities, said he “respectfully” disagrees with Wu’s view of the permitting progress.

But the two sides are willing to talk about another option for accessing Long Island: ferries — an idea Walsh and former Boston acting Mayor Kim Janey both studied but never advanced.

Wu has characterized Long Island as a longer-term solution to the drug and homelessness issues the city is dealing with at Massachusetts Avenue and Melnea Cass Boulevard. She cautioned on OTR that either a bridge or ferry service would be costly — prior estimates for transportation and a new recovery campus have been in the range of hundreds of millions of dollars. And she said either could take “multiple years” to build or implement “no matter how accelerated a timeline is.”

Still, her administration’s incremental progress on the bridge stands as one example of how Wu is quietly making inroads on both her initiatives and issues that she inherited — like the twin crises at Mass and Cass — even as some of her flashier proposals stall.

GOOD MONDAY MORNING, MASSACHUSETTS. FWIW, Gov. Maura Healey is supportive of restoring Long Island as part of a broader push to expand access to long-term treatment and recovery, an administration spokesperson said.

TODAY — Healey has no public events. Wu attends a coffee hour at Brighton Commons at 9:30 a.m., is on WBUR’s “Radio Boston” at 11 a.m. and hosts a press conference on street safety at 12:30 p.m. in Mattapan. Rep. Richard Neal and Sen. Ed Markey attend a Berkshire Family YMCA ribbon-cutting ceremony at 11 a.m.

Tips? Scoops? Screamed yourself hoarse at Taylor Swift (or Blink-182, or Janet Jackson, or at the Celtics)? Email me: [email protected].

— ROLLINS RESIGNS: “The rise and fall of Rachael Rollins,” by Mike Damiano, Milton J. Valencia and Matt Stout, Boston Globe: “On Friday, months into her tenure as US attorney, [U.S. Attorney for Massachusetts Rachael] Rollins resigned, after two bombshell federal reports documented a multitude of ‘egregious’ and ‘blatant’ ethics violations. In the days since the reports were released, critics and supporters alike have pored over Rollins’s record, highlighting her successes and missteps, and reexamining warning signs that might have foretold her spectacular fall.

The story that emerges is one of an ambitious reformer intent on righting the wrongs of a justice system she saw as unjust, but also of a hard-charging political star who seemed to believe the rules of the system she sought to change did not — or should not — apply to her.”

— STEPPING UP: Joshua Levy, the first assistant U.S. attorney under Rollins, is now acting U.S. attorney for the district.

— FALLOUT CONTINUES: “Boston City Councilor Arroyo denies working with Rollins to tip election outcome,” by Gayla Cawley, Boston Herald: “Boston City Councilor Ricardo Arroyo denied colluding with former U.S. Attorney Rachael Rollins to influence the outcome of last year’s election for Suffolk DA. Arroyo told reporters Friday that he had no knowledge that Rollins was leaking sensitive information on his behalf, and denied pressuring the state’s top prosecutor to investigate his primary opponent.”

— CONTROVERSIAL CONGRESSMAN: Rep. Jim Jordan (R-Ohio) drew denunciations from Democrats and protesters on Cape Cod as he lined his campaign coffers with Massachusetts money in a series of weekend fundraisers across the state.

The chair of the powerful House Judiciary Committee and an ally of former President Donald Trump who supported his challenges to the 2020 election, Jordan barnstormed the Bay State to raise money for his eponymous Freedom Fund. He was at former MassGOP Chair Jim Lyons’ Andover barn for a fundraiser on Saturday. Tickets ran as much as $5,000 a head for a Sunday evening event hosted by auto-parts magnate and Lyons ally Rick Green at a restaurant in Boston’s North End. And they topped out at $16,600 for a brunch hosted by Michael King of the conservative nonprofit Massachusetts Family Institute and others on Saturday morning in Lincoln, per invitations reviewed by Playbook.

Demonstrators protested Jordan outside his rally at Cape Gun Works with former GOP attorney general nominee Jay McMahon on Sunday, per WBZ NewsRadio’s Tim Dunn. Democratic Cape Cod state Sen. Julian Cyr also condemned Jordan’s visit to the peninsula, saying in a statement that by “inviting a national figure who has made his name peddling in election denialism, homophobia, and bigotry, local Republicans are legitimizing dangerous and undemocratic propaganda.”

— “New hope for bill to ban size discrimination in Massachusetts, after three decades of trying,” by Jeremy C. Fox, Boston Globe: “Massachusetts residents … could demand better treatment in medical settings, the workplace, and recreational areas under a bill before the state Legislature that would ban discrimination based on weight or height — a proposal that may have fresh momentum after a similar measure passed the New York City Council this month.”

— “‘Don’t mess with pitch’; bills seek gambling exception for small-stakes games at senior centers,” by Jonah Snowden, Springfield Republican: “State Reps. Angelo Puppolo and Brian M. Ashe have filed separate bills that would allow legal — and limited — gambling in senior centers. Puppolo’s bill, H. 1724, would allow for legal gambling through card games, including poker, pinochle, bridge, rummy, canasta, hearts, dominos, cribbage and any recreational bingo in the commonwealth.”

— “‘Taylor Swift bill’ aims to make ticket prices transparent in Massachusetts,” by Maya Yang, The Guardian.

— “Boston City Council remains at odds over redistricting as deadline approaches,” by Gayla Cawley, Boston Herald: “Four different redistricting maps were brought forward for discussion Friday, but Ruthzee Louijeune, chair of the Council’s civil rights committee, opted to dismiss proposals from Mayor Michelle Wu and two other councilors, in favor of using her own map as a ‘starting point.’ … The decision, however, was met by some grumbling by her colleagues, particularly from Councilor Kendra Lara, who said the map she put forward was less disruptive than Louijeune’s proposal.”

— “Boston Common rally protests GOP efforts to force US to default on debt,” by Danny McDonald, Boston Globe: “‘You shouldn’t have to demand that the GOP stop extorting American families and yet here we are, less than two weeks from unprecedented catastrophe,’ said Representative Katherine Clark, the House Democratic whip, during a news conference that preceded the rally.”

— “U.S. Rep. Richard Neal says east-west rail ‘is going to happen’ in push for regional equity,” by Jim Kinney, Springfield Republican: “Things have been quiet lately with east-west rail, the Pioneer Valley’s decades-long quest for better and more frequent passenger train service to Boston. But that’s changing, says a leading proponent, U.S. Rep. Richard E. Neal, D-Springfield.”

— “Guardsman Jack Teixeira, Pentagon leak suspect, to remain jailed as he awaits trial,” by Marco Cartolano, Telegram & Gazette: “A federal magistrate judge in Worcester said Friday a Massachusetts Air National Guard member charged with leaking highly classified military documents will remain behind bars while he awaits trial.”

— “Recall of Easthampton School Committee chief begins,” by Emily Thurlow, Daily Hampshire Gazette: “Vexed by the way the School Committee has handled this spring’s failed superintendent search, city residents this week officially began the formal process to recall Chairperson Cynthia Kwiecinski.”

— “No winner, again, in West Stockbridge Select Board election recount. What’s the next step?” by Clarence Fanto, Berkshire Eagle: “A painstaking, laborious electronic recount on Friday yielded the same vote totals for Select Board Chair Kathleen Keresey and challenger Jon Piasecki: 202-202. … The election process heads back to square one.”

— POMP AND CIRCUMSTANCE: “Dr. Driscoll addresses fellow graduates at SSU,” by Dustin Luca, The Salem News: “It was a commencement address 34 years in the making [for Lt. Gov. Kim Driscoll].”

— “Charlie Baker tells Bentley graduates life is a series of choices and challenges,” by Laura Crimaldi, Boston Globe.

— “‘David Zaslav, pay your writers’: Protests erupt as Warner Bros. executive gives BU commencement address,” by John Hilliard and Samantha J. Gross, Boston Globe.

— “YouTubers film, insult public workers in towns across Mass. for self-declared ‘First Amendment audits’,” by John Hilliard, Boston Globe: “The scuffle in Lexington’s public library last month was short but seen by thousands: a patron grappled with another man as they wrestled over a camera tripod, as the confrontation was livestreamed on YouTube. Two men, Joshua Abrams and Leonard Filipowski, had set up the camera inside the library to conduct a so-called First Amendment audit, a kind of performative protest that tests their free speech rights by confronting government employees in public places, often provoking objections that generate viewership.”

— “While student chronic absenteeism numbers remain high, Boston and Mass. show signs of recovery,” by Christopher Huffaker, Boston Globe.

— “Former Sen. Scott Brown hosts 2024 GOP presidential contenders in NH as he mulls another Senate run in 2026,” by Paul Steinhauser, Fox News.

— MEETING OF THE GOP MINDS: Florida Gov. Ron DeSantis met with New Hampshire Gov. Chris Sununu for an hour on Friday as part of a jam-packed day of glad-handing and baby-kissing (literally) ahead of his expected presidential campaign launch. The two potential rivals discussed how to do well in the first-in-the-nation primary, among other topics, per Sununu’s office.

SPOTTED — Swifties out en masse for Taylor Swift’s three-night extravaganza at Gillette.

Night one: Gov. Maura Healey spokesperson Karissa Hand, Patriots QB Mac Jones.

Night two: POLITICO alum and The Block’s Stephanie Murray, Kunal Botla and the “rainiest rain show that ever rain showed.”

Night three: state Economic Development Secretary Yvonne Hao, Carolyn Chou of the Asian American Resource Workshop, Sharon Select Board member Hanna Switlekowski, Boston B-Side’s Emily Schario and incoming Boston Housing Authority Administrator Kenzie Bok, per tipsters and tweets.

ALSO SPOTTED — at Blink-182’s concert at the TD Garden last night: noted fan of the band, former Gov. Charlie Baker.

AND ALSO SPOTTED — at Janet Jackson’s concert Friday in Mansfield: former Boston City Councilor Annissa Essaibi George.

HAPPY BIRTHDAY — to the DNC’s Kristen Orthman, an Elizabeth Warren alum; former state Rep. Linda Dean Campbell, Noah Feldman, the Boston Globe’s Shira Schoenberg, Casey Pease, Juli Hanscom, Mary Dooe, the Globe’s Christina Prignano Deering, Oren Cass, Peter Weissenstein and former Patriots wide receiver Julian Edelman. Happy belated to Arthur Brooks and Nicole Freedman, who celebrated Sunday.

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