In honor of the holiday season, we present this magical tale of underdog grit, triumph over evil, and old men weeping in the streets. Lifelong Red Sox fan Tyler Rotman joins me to tell me the tale of how the curse was broken and the city liberated from its insidious vice — even if Pedro did throw that old man to the ground.

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We're back from vacation and learning all about this iconic Boston neighborhood. Our guest Pat Toomey (not the former senator!) explains old working-class-Irish Southie and new frat-bro-central Southie, and even gets in a few digs at "The Departed."

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Hope you're hungry! We're digging into this regional delicacy with the man behind a 50k-strong community dedicated to discussing North Shore roast beef.  Andy Ferg tells me what makes a great sandwich — freshness matters — and why some of the most famous shops rest on their laurels. Warning: This episode  contains adult language. Lots of it.

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In this episode we're joined by the host of GBH News' "The Big Dig" podcast to talk about the city's most infamous infrastructure boondoggle. Who were the major players? Why did America spend so much of the middle of the 20th century running highways through historic urban cores? And in the end, was The Big Dig worth it?

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This week, I'm learning about the Boston Pops, a  beloved local institution. We're talking Arthur Fielder, we're talking John Williams, we're singing the Superman theme, we're hearing about the largest firework in history (spoiler: it was a dud), and the creation of the field of acoustics. Plus, giant pumpkins floating on the the Charles, Phillies talk, and musings on what it's like to live with the Liberty Bell. 

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We're diving into Boston's comedy boom with Nick Zaino. The Boston Globe writer tells us about the legend of the Ding Ho, swears in the name of Dennis Leary, and awes me with the names of famous comedians that just happen to be from here. Plus, a story about how to make an enemy of host Lee Stabert: It involves being tall and wearing a large hat. 

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This week I'm learning about how, in the 1970s, Boston became the poster child for desegregation strife in the North. Professor Matthew Delmont of Dartmouth University shares his insights on the deep structural issues that led to the busing crisis, the role of the media, and how the city's reputation as the "cradle of liberty" led to a fascination with its racial woes.  Plus, I talk about the Phillies.

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I'm joined by Leila Cohan, TV and movie writer extraordinaire, to talk about running errands in the suburbs, the joys of a bad mall, killing time in Copley Place, and how Legacy Place personifies the new, pricier, more chain-happy Boston metro. 

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If you heard the phrase "Massachusetts Miracle,"  would you also assume it was a famous sports play? Please tell me I'm not alone. In this week's episode, we're joined by Cambridge native and history professor Lily Geismer to talk about Route 128, the associated tech boom, suburban liberals, and famous loser Michael Dukakis. Plus, I've got more to say about Duck Boats.

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This week I'm joined by a transit influencer, which is a thing I just made up. Fellow Boston transplant Jed Paul (@jeddeo1 on TikTok and Instagram) is a lifelong train enthusiast who has made it his mission to explore the MBTA, warts and all. Come for the deadpan, absurdist humor, stay for tales of the mysterious blue line, bulging walls in green line stations, and Mark Wahlberg. 

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