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David Kasprisin, Branch Manager

Wintrust Mortgage


Having been involved with the origination of nearly $5 billion in mortgage funding since 1995, David Kasprisin is happy he can still say that every day at work is different. “Rules and policies change constantly, so it’s like working a new crossword puzzle each day,” says Kasprisin, a branch manager for Wintrust Mortgage. “Not only do you have to remember what the new rule is, but you also have to forget the old rule.”

Thankful for the opportunity to work in the industry, the loan process is incredibly meaningful to Kasprisin. He’s earned Wintrust’s highest level of achievement — the President’s Circle Award — each of the eight years he’s been there. Prior to that, Kasprisin had consistently won similar awards at other companies, including in three different categories, as originator, manager and area manager. But he doesn’t like to focus on the honors. “When I get a card from a client that says, ‘You made this possible,’ that is all I really care about,” he says. “I put it in my drawer and go back to work.”

Kasprisin didn’t always work in lending. He earned a master’s degree in education and history and taught at Whitney M. Young Magnet High School. “Being a lender requires you to explain the process in easy-to-understand terms,” he says, noting that teaching gave him the skills to do that. “Just as importantly, my passion has always been to help people develop the skills necessary to make good decisions and reach their potential. That is why I have had leadership roles throughout my career.”

Managing several large production groups through different economic cycles exposed Kasprisin to nearly every possible loan scenario. “It’s rare when I haven’t seen something,” he says. “But it still happens, which makes every day unique for me. Not a lot of people have that in their careers.”

Regardless, it’s his two loving and kind daughters who inspire him the most. They lost their mom — Kasprisin’s wife, Holly — four years ago, when they were entering adolescence. The loss was traumatic, but the girls have blossomed in spite of it, thanks to the love and support of family and friends. “They bring sunshine to the lives of everyone around them,” he says.

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