The Back 9 - Midlife, Best Life.

Old friends become increasingly valuable as we get older. But keeping those friendships alive takes a little more intention than it used to.

For our Season 14 finale we return to the 19th Hole to talk about the friendships that have carried us through different chapters of life, why reconnecting matters, and how those relationships change as we do.

We also look back at a season of fascinating guests who reminded us that career reinvention doesn't always require a new beginning. Sometimes it's about rediscovering what we love about the work we already do, and letting go of what no longer serves us.

Plus, Sober October, and a (dry) toast to 14 seasons of figuring things out together on the Back 9

Have you ever taken the time to think about who introduced you to something you love, and to appreciate what that person gave you? Fresh off a golf trip to England, Dennis shares a toast he made to the people who first put golf clubs in our hands. It's a fitting introduction to this week's guest on The Back 9, longtime golf writer and editor Evan Rothman. Evan still plays with his 93-year-old father, who introduced him to the game, while watching his own son compete at the collegiate level. Three generations, and some hard-earned lessons about parenting, ambition, and knowing when to step back. After decades profiling some of the biggest names in entertainment and sports, Evan also reflects on why prestigious bylines matter less than they once did, and why the stops on our careers shouldn't define who we are. It's a conversation about the people who shape us, the ambitions that drive us, and how our perspective changes as we make our way through the Back 9.

Are young people really less motivated than previous generations, or are they set on building a future in a world that looks nothing like the one their parents grew up in?

This week, we welcome Ariel Feldman, the 25-year-old creative force behind much of The Back 9's social media. Ariel shares the hilarious story of how she essentially stalked Dennis into hiring her, then offers a Gen Z perspective on careers, financial pressures, social media, AI and the expectations older generations place on younger ones. Dennis and Josh push back, and a lively debate follows about ambition, work ethic and what generations can learn from each other.

Ariel is also moving on to an exciting opportunity with HeadCount, a voter registration organization that works with major musicians. Her next assignment? Touring with Olivia Rodrigo. Apparently, working with two aging sportscasters wasn't glamorous enough.

It's a conversation about mentorship, taking chances and learning to listen across generations...on The Back 9.

After decades in Hollywood, Paul Adelstein still isn't sure he's made it. And maybe that's part of what's kept him going.

This week on **The Back 9**, the star of *Private Practice*, *Prison Break*, *Girlfriends' Guide to Divorce* and *The Audacity* joins us to talk about his unlikely start in Chicago theater, his big break with John Cusack, and the experience of growing older in an industry where the roles change right along with you. And how did his high school class manage to produce four successful Hollywood actors, including one who became a major star?

Along the way, Paul shares stories of old friends, famous collaborators, divorce, fatherhood and what it means to keep challenging yourself creatively.

For Paul, success isn't necessarily a role, a paycheck or a particular milestone. It's doing meaningful work with people he respects and staying excited about what might come next. Not a bad way to approach the Back 9.

Divorce has a nasty habit of turning bad decisions into permanent ones.

This week on The Back 9, mother-and-son appellate attorneys Amy Shield and Roger Levine, authors of Divorce SOS, share the legal mistakes people often don't recognize until it's too late — from financial records and settlement agreements to choosing the wrong attorney.

But some of their best advice happens outside the courtroom. When an ex knows exactly how to push your buttons, that angry text or email can feel pretty satisfying, until it gets used against you.

Amy and Roger join us to talk about lowering the temperature, protecting your kids and finances, and making decisions today that you can still live with tomorrow...and all the way through your Back 9.

Being engaged with the world doesn't mean we have to let all of it into our heads. This week on The Back 9, it's just Dennis and Josh, talking about everything from the crime against humanity that is mixing 12-year Scotch with Coke to movies, anxiety, meditation, social media and the things we allow to occupy way too much space in our lives. Dennis shares what happened when he dramatically cut back on social media. Josh talks about recognizing his own anxiety around conflict. And together, we wrestle with a bigger question: how do we stay curious, informed and connected without getting consumed by all the noise? Maybe the answer isn't disengaging from the world. Maybe it's becoming more intentional about how we engage with it — and what actually deserves our attention.

Sometimes we get to a point in life and realize that we are spending so much time focused on the future for our family, that we've lost sight of the life we're living right now. This week on The Back 9, entrepreneur Philip Crutchfield talks about becoming a father young, building successful businesses, and confronting his own role in the end of his second marriage. Philip spent years working long hours and traveling to give his family a life he never had, only to realize -- a little too late -- that they already had a pretty good life. Now 50, with four children, he reflects on ambition, fatherhood, divorce and the years we can't get back. Sometimes figuring out what happened isn't about assigning blame. It's about recognizing what we want to do differently with the years ahead. It's an opportunity to change the game -- on the Back 9.

Divorce can feel like the worst thing that's ever happened to you. For Kurt Heide, it once did. When his first marriage ended, Kurt suddenly found himself raising three young children as a single father while trying to hold together his career and his life. This week on The Back 9, he shares what he learned about putting his kids first, keeping anger from driving important decisions, and eventually building the relationship he's now been in for 18 years. Kurt also talks about his work with the National Association for Divorce Professionals and why the right legal, financial and emotional support can matter when you're least equipped to make clear decisions. Because the choices we make during the worst moments of our lives long after it's over, and that's a lesson worth heeding on the Back 9.

This week on **The Back 9**, ESPN 1000 Chicago's **Marc Silverman** joins us to talk football, fatherhood and the non-Hodgkin's lymphoma diagnosis that changed the way he thinks about his time.

Now six years in remission, Silvy shares how therapy, mentorship and even acupuncture helped him through treatment—and why he no longer puts off the trips, experiences and time with his wife and sons that once could have waited.

Dennis also opens up about his own experience with prostate cancer, including why he chose to handle parts of it very differently.

Two dads. Two cancer journeys. And a conversation about health, family and why some things are too important to save for later...on the Back 9.

Three years ago, The Back 9 was born over late-night hot dogs and cheese fries at Chicago's legendary Wiener's Circle. This week, we sit down with one of the guys who owns it. Investor and restaurant owner Ari Levy talks about preserving—and reinventing—a Chicago institution famous for its irreverence, and how the Wiener's Circle became part of the conversation around the Bears last season with viral stunts involving Ben Johnson, Caleb Williams and more. Then we make the turn. After two divorces, Ari opens up about therapy, fatherhood, taking better care of himself, and finding an unexpected relationship with one of his closest friends from college. It's a conversation about what experience teaches us to value in a partner—and why friendship, shared values and simply enjoying each other's company may matter a whole lot more the next time around.