Pilgrim Mortgage Celebrates Twenty Years
It Started with Belief
Twenty years ago, Pilgrim Mortgage opened its doors with a handful of people, a lot of belief, and absolutely no guarantees. There was no playbook for what the Pilgrim brothers were building. No safety net. Just a shared conviction that they could do this differently, do it better, and build something that would last.
That origin story, modest in resources, but enormous in ambition, is worth revisiting as we mark our 20th anniversary. Because understanding where we started is the only way to truly appreciate where we are.
The Road to Twenty wasn't Straight
No company survives two decades without weathering storms. For Pilgrim Mortgage, those tests came early and often.
The 2008 financial crisis shook the entire mortgage industry to its core. While many lenders collapsed or retreated, Pilgrim stayed the course; a testament to the steady, client-first culture the founders had built from the beginning. It would have been easy to scale back, to play it safe, to wait it out quietly. Pilgrim chose to keep showing up.
Then came 2020. The COVID-19 pandemic brought a kind of uncertainty the industry had never experienced before. Closings went virtual. Teams went remote. The market swung wildly between paralysis and a pandemic-fueled buying frenzy that put extraordinary pressure on every process and every person. Through all of it, Pilgrim remained not just operational but resilient, emerging from the chaos with momentum intact and a team that had proven it could handle anything.
This milestone isn't just about time. It is about every single first closing, every tough market navigated, every big win celebrated. Our shared story is one of resilience and hard work, and it didn't happen by accident.
Growth through Unity: the Next Phase of Pilgrim Mortgage
One of the most defining chapters of Pilgrim's story didn't come from enduring hardship, it came from choosing connection. In 2022, Pilgrim Mortgage was purchased by Wes Kleckley, one of San Antonio’s largest loan officers, effectively combining Pilgrim Mortgage with the Kleckley Mortgage Team. This brought together two complementary cultures, client bases, and visions together under one roof. The result was a single, stronger company with renewed energy and expanded capability.
With a new roadmap in hand, Pilgrim Mortgage began on an unprecedented trajectory. Growth boomed and expansion pressed onward. And in 2025, record production months were posted. The next chapter was officially well under way.
This Milestone Belongs to Everyone
Twenty years isn't just a number. It's the sum of every client who trusted us with the biggest financial decision of their lives. Every loan officer who made one more call, worked one more late night, found one more creative solution. Every referral partner who sent someone our way. Every team member, past and present, who showed up and gave their best, even when the market made it hard.
Whether an employee has been with us since the beginning, or walked through the door last month, they are now part of this story. However they’ve contributed, they are part of the next chapter. And that's not a small thing, it’s everything.
Pilgrim Fridays: Wearing Our Story in 2026
To honor this milestone all year long, Pilgrim Mortgage is launching "Pilgrim Fridays" — a simple but meaningful tradition where the entire company wears their Pilgrim shirts every Friday throughout 2026. Pilgrim Fridays are a weekly, visible reminder of where we came from, what we've built together, and the team we're committed to being going forward.
In an industry that can feel transactional, these kinds of rituals matter. They say: we are not just colleagues moving files from one desk to another. We are a team with a history, a culture, and a shared sense of pride in what the name Pilgrim Mortgage represents. Every Friday, we wear that pride.
The Next Twenty Years
The past few years have been supercharged. We've grown. We've evolved. We've proven, again and again, that Pilgrim Mortgage is built to last. And while this anniversary is a moment to look back with deep gratitude, it is equally a launching pad for everything that lies ahead.
The next twenty years will bring new markets, new technology, new regulatory landscapes, new challenges, and extraordinary new opportunities to serve clients at the highest level. There will be moments that test us, just as 2008 and 2020 did, and when those moments come, we will face them the same way we've faced everything since 2006: together, with belief, and with the kind of hard work that has always defined this company.
Here's to the next chapter, and to every person who will be a part of writing it.
Wes Kleckley
President/CEO, Pilgrim Mortgage
wes.kleckley@pilgrimmtg.com
