🎙️ Episode 108: Red Sox Digest LIVE! - Special Guest: Tony Massarotti from 98.5 The Sports Hub

🎙️ Episode 108: Red Sox Digest LIVE! - Special Guest: Tony Massarotti from 98.5 The Sports Hub

From Red Sox Digest Podcast by Red Sox Digest

July 2, 2026 · 1h 19m · Season 2 · Episode 108

About this episode

The episode features Tony Massarotti discussing the Red Sox's struggles and potential trade decisions.

Watch the full episode below 👇Episode SummaryThis episode of Red Sox Digest LIVE featured special guest Tony Massarotti from 98.5 The Sports Hub, and the panel went deep on the state of the Red Sox after another ugly series loss, this time to the Nationals. The show opened with the Willson Contreras debate: whether his right-handed power is too valuable to move or whether the tirades, ejections, and daily chaos make him a deadline trade candidate. From there, Mazz and the crew tore into the bigger organizational mess — Craig Breslow’s future, whether ownership is really letting him run the deadline, the Red Sox’ inability to build a complete lineup, the failed player development pipeline, the mishandling of Rafael Devers, and whether this franchise has completely lost its identity. The conversation also hit Fenway becoming more museum than home-field advantage, the obsession with analytics, the failures of top prospects, and the long list of turning points that helped drag the Red Sox into their current baseball swamp.Takeaways* Tony Massarotti still leans toward keeping Willson Contreras because the Red Sox desperately need right-handed power, but he admitted the headaches are…

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