“Champion of the Underdog”
When pessimism is just a disguise for heart-deep belief
Friday, July 11 — 89 days to go.
This morning’s email hit me differently. It wasn’t about pain or policy or how to survive another day. It was about something bigger: the kind of man Matt is when nobody’s watching. The kind who, even in a system built to strip men down, keeps trying to build others up. The kind who reminds people who’ve been told they’re nothing… that they’re still good.
It’s an email about belief — not just in himself, but in people who’ve forgotten how to believe at all.
Matt shares that as guys around him prepare to leave, many forget they’re still good people. The system doesn’t remind them — it erodes them. So, Matt has started saying it aloud: “You’re a good man.” It might not change everything, but it might spark something.
He knows what it’s like to carry the weight of judgment. And he knows it’s worth fighting that weight — not with bitterness, but with relentless faith in who you really are. Not what happened to you.
It’s not optimism he claims to have — he even jokes that “super optimism” is something the BOP sees as suspicious. But the truth is, he’s always believed in us. In this life we’re building. In the quiet miracle of making it through with our heads and hearts intact. And if that’s criminal thinking — he says — then so be it.
Matts letter
It's been an interesting day. My "artistic" skills, such as they are, have once again been called upon to help liven up the exercise studio. Since I'm doing yoga in there anyway, they asked me to re-work the board with some other information because the guy who runs that area is going to start offering classes for compound staff. I don't think this requires a ton of creativity - he basically told me what he wanted, so I may mosey over there tonight and work on that, instead of getting too into a class just yet. Kind of want to see where this other stuff physically goes first before I go down that path. One good development there, though, is that he cleared out even more space in there, so if our numbers ever really did go up significantly, we could accommodate them. Like my class, he knows he may end up with anywhere from 2 to 15 people, so you gotta have space.
And speaking of space, I officially signed my paperwork to leave the compound every day for the community service work, so I no longer will be needed to try to edumacate anyone on space travel, writing, GED math, or why Empire is the best Star Wars movie (or any movie for that matter) of all time. I let the staff there know, and they were very kind as I wrap things up. I made sure to express how much I appreciated the opportunity to spend some time here doing something worthwhile, but that it's also time to move on and let a new crop of convicted felons show their fellow convicted felons how to figure out a square root. I also ran into the associate warden, who still wants me to come by and discuss the way BOP calculates our time, which I think it's possible that they really do not know. In all, they were mini interactions with staff today that had a much different feel than anything previous. Maybe it's just getting to the end, or maybe the relief of having my date made those interactions seem less strained to me - and possibly to them. I'm happy to go over there sometime next week and walk him through the analysis (it's not really that complicated) and also look forward to starting the new assignment. I think it'll make the final 2 months fly by.
One guy who left today tried everything he could to mess things up. He almost did, and even after he was gone there was some speculation that he might be sent back. He helped land one of the newbies in hot water, and that was potentially ugly. Seeing it all go down reminded me of why the head-down-grind-it-out approach has been so vital. It's what they want to see, and nothing we could do here would be worth jeopardizing their trust in us to get us home. Guys get denied discretionary time a lot, and they always complain about it being someone else's fault. It isn't. But one of the challenges is that the evaluation process the staff here uses is never fully explained to these guys. They're looking for what they see as "criminal thinking" and all kinds of things lead them to determine whether a guest will likely go home and be good, or whether they're coming back. From the simplest things, like guys complaining about what they do and do not "get" (that falls into the category of entitlement and victimhood that staff considers) in terms anything from of time off their sentence, to perks and meals, this is the most common thing people here howl about, and all that anyone would ever have to tell them up front is that they don't "get" anything, but they can ask how they can earn all sorts of things. Just a different mindset than the typical criminal thinking. But no one ever does.
I remember talking to a guy at Milan who, through an extremely unusual set of circumstances, was required to be resentenced for his white collar fraud. Essentially, he was stealing from his clients as a financial advisor and got whacked pretty hard for it. He admitted to his actions and I think he got 12 years or something like that. But the court lost his transcript, or deleted it by accident or something, so in order to make everything legal, they were forced to do it again. He was gleeful to have another crack at it. He was also one of the lampreys, so I heard about this ad nauseum. His explanation, he claimed, was that it started small, and before he knew it, things had snowballed to the point where he was taking millions from his victims. This, he believed, would sway the judge that he had never intended to get so out of control, and would end up with a sweeter sentence. That didn't happen. The judge dismissed his excuse as soon as he justified the "small" part of the crime, and tried to use it to excuse the rest. This was pure criminal thinking, according to the judge, and he threw the book at him again. In fact, he ended up being lucky, probably, that he hadn't gotten *more* time. The lesson of that episode was to ty to learn to think like people in corrections do, tailor our behavior to whatever that is, and demonstrate that we could be trusted to go home sooner. I'm not saying I've mastered that art, or any art (well, except white board art apparently), but I did my best to see the path to my future through the lens of what these people are looking for, but never tell us. Seeing the newbie struggling with his situation, brought me back to my initial days when everything was new and heavy. It wasn't the disorientation that I remembered from those days as much as the weight of the time ahead of us. Knowing we had many milestones to pass before we could even think about getting home and being whole again. Those were lonely moments - and the only way to conquer them was to do the work, so that's what we did. Now, as the grizzled veteran of the system, we're pointed toward the end. I think we can say that we did it right, and were rewarded for our approach, regardless of how we felt about me having to be here in the first place.
Some guys handle it better than others. On that score, I made two decisions today. The first, is I asked a few of the deer-in-the-headlights guys to be aware of a couple of concepts. First, if you don't see anyone else doing it, you're probably not supposed to be doing it either. Not that all the stuff people do is okay, but if you happen to be the only one outside at any given time, it's a good idea to check and see if there had been a recall or something. If you don't see guys exchanging their items from commissary or anywhere else, you might not want to do it either. Basically, they just need to be more aware of their surroundings, and start to take it all in. I know I had to - and one bad decision early on because they're still in denial about their circumstances. I remember a couple of guys at Milan remarking that I wasn't "there" yet when I first got there. Those guys need to get here - and do it now. The other thing I asked them to do is forget their old sense of fairness or expectations of politeness, etc. Those no longer exist here, and they can get back to that when they get home. They may think a rule is stupid. Out in the world, that's a good reason to flaunt it and let everyone know where you stand. Here, it just means trouble, and no one cares what we think of the rules. Time to put those things away. I don't even remember how I handled the first few days and weeks. We just committed to getting through it, and that's what we did. it actually sucks to be one of the guys who knows his way around these parts a little bit better. It just means we've been in here longer, away from our families for a while, and out of touch with what goes on in the rest of the world. The only good thing is that we're coming near the end. For as long as I've been in this population, guys have been "short to the door." Not sure if I'm quite there yet, but today is 89 days away. One by one, they keep falling to the side, behind us forever, never to be found again.
The other decision I made today is to remind every guy I see leaving to remember that they are a good person (if they actually are, I won't say this to everyone) because that idea gets slapped out of a lot of us for various reasons. Just the simple act of accepting responsibility for the things we did wrong can wreck a person's ego. It's where I think all this criminal mindset stuff misses the mark. By the time we're finishing up, there should be an effort to build guys back up. There's no such thing here. Beaten down and demeaned until the day they leave, I think some guys hit the door forgetting that they're a good human being, who may have done something wrong - not the opposite. Believing in themselves can help them reconnect with their families, re-enter their communities, and start building a new career (or rebuilding an old one). Not that a few words from me is going to change the way guys see themselves, but for a lot of them, people stopped reminding them of their goodness a long time ago. When people stop saying it - especially when they want to constantly remind the world what a piece of sh*t they think you are - eventually men stop saying it to ourselves. If we accept what the world wants us to be seen as, we're letting losers win. That should never happen. I thought that having someone say the words might spark something within them to search that out from people who mean more to them, the people whose opinions actually matter. But if they accept the worldview that they are defined by what happened to them in the worst moments of their lives, then they might as well stay here, or be certain that they'll be back.
How we managed to stay away from all that for all this time is a miracle - assuming we actually did that. We have no reason to fear the judgement of our family, friends, and neighbors. Anyone who doubts us doesn't know us, and the people who do know us have total faith. That's been both our blessing and our burden at times in our lives, but it's not about what anyone owes us, it's what we've earned. Being a federal prosecutor, or one of the simps who cheers them on, is like playing a tennis match against an opponent with no racquet, having the umpire call all your shots in and all his shots out, and then celebrating like you've accomplished something when you inevitably win. That's what losers do, because they're too afraid to face an evenly-matched opponent, but that's who has the power to put us through things like this. It needs to change, and someday, hopefully, it will. Until then, all we can do is deal with what we have in front of us. And what we have now is the end of a long journey. If we look back at all, it's to congratulate ourselves on having survived it. Otherwise, I try not to. But when I see a familiar look from someone just starting their own journey, or hear some of those same conversations we used to have, it can't help but stoke some of those old feelings, and make me remember the harder times. Things are better now, and everyone warned me that coming near the end means the days will start to seem like they're dragging. Not here at least, and certainly not today.
Yesterday was momentous, and with probation contacting you for a home visit, we're checking all the boxes for what the end looks like. For two years now, I've heard guys talk about that process. Until very recently, I wouldn't even allow myself to wonder what that awesome news felt like. It only happened to other people, after all, it seemed like it may never happen to me. And given everything else we've been through, there was little reason for hope that this process would go the way it was supposed to, even with the maximum effort we put into getting the best result we possibly could. But we finally did it. Tomorrow I'll go find out what they saw on the x-ray, and then we'll take care of that situation. By the end of the month, I'll be out in the community, getting to feel like a semi-normal person again for most of the day, 5 days a week. I'm sure we'll add some more insights, and keep preparing for life once we can get back to us.
I looked at a list of the criminal mindset things that staff looks for. One of them is "super optimism." I chuckled to myself that the term couldn't possibly apply to me. Most people who know me would probably think I'm the opposite - a super pessimist. But in this situation, I've somehow never lost faith, always believing that what was right would eventually happen. It never has, but all sorts of other good stuff has along the way. I think that wouldn't've been possible without us holding on to that faith, and if that's criminal thinking, then so be it. One thing I know we never lost faith in is ourselves, and each other. The only way to fuel that fire and keep it burning through all this was by never wavering from our ability to dream. I'm glad we never lost that.
There will be more interesting days ahead, but maybe not many as big as the ones from this week. As the countdown dwindles, I'll just focus on feeling lucky that we chose the path we're on, and most important, that we found each other.
Will call at 6. Love!!
- Bunny
Kate’s Reflection
If you’ve ever watched Matt watch sports, you know: he is a world-class pessimist when it comes to the scoreboard. Up 20 with 30 seconds left? He’ll still find the one unlikely scenario where it all goes wrong. And yet — when it really matters, when it’s real life, when the odds are long and hope feels foolish — he turns into the most relentless optimist I’ve ever known.
He bets on the underdog every time. And not just as a fan — as a fighter. He throws his full heart, brain, and body into the ring. When we were handed the worst possible version of this story — two years ripped from our lives, a system stacked against us, and no road map — he didn’t give up. He doubled down. On dignity. On belief. On me.
The last three paragraphs of his email are a view from 100 feet above. He’s zoomed out, surveying the road we’ve walked. And instead of bitterness, he’s reaching back to lift others. Reminding them they’re not broken. That they’re more than their worst day.
If there’s a lesson here, it’s this: true optimism doesn’t mean you always feel good. It means you refuse to forget the good that’s still in you — and in others — no matter what.
That’s the kind of optimism Matt lives. And that’s the kind that changes lives.
🧭 Closing Line
If you’ve forgotten you’re the underdog — or that the underdog can still win — let this be your reminder.
🚀 Call to Action
Today, remind someone that they’re still good. Say it out loud. Write it down. Whisper it if you have to. You never know who’s waiting to hear it — or who might rise because you did.