Jack K. O’Leary

1945 ∼ 2020

Jeff Boss of Woburn, MA wrote:

Jack was one of kind. He was a generous man with constant cheshire grin that made him endearing and a lot of fun to be around. My heart goes out to Eileen, Maureen, Tim, Janice and the entire family. God Bless

Jen Sousa of Taunton, MA wrote:

You’ve touched my heart, and I have no doubt you have touched thousands. This world will miss you Jack ❤️

Chris Turcotte of Brockton wrote:

I will miss Jack, and his sense of humor and generosity. He was always willing to lend an encouraging word, or to impart his knowledge and teach. I'm thankful for the times spent both at the office and in his home. My best to the family in this difficult time.

Brian & Kathy Murphy of Easton, MA wrote:

Be assured of our prayers for Jack & the extended O’Leary family.

Michael Wilson of Buffalo, NY wrote:

You will be missed.

Harris Sandler of Rahway, NJ wrote:


BRIAN OREILLY of Boston wrote:

Rest In Peace Jack. My thoughts and prayers are with your family and friends.

Michelle Fermin of Boxford, Ma wrote:

May you rest in peace Jack. Always in our hearts

Laura Dietz of North Hollywood California wrote:

Sending Love and many prayers to all of you in this loss. I remember Jack with many happy memories. He was a great man with a kind and loving heart. So Sorry

Michael Krein of Henderson NV wrote:

For My Best Friend – Jack O’Leary Today is an incredibly sad day for all of us. For myself especially as last night I lost my best friend. Not only my best friend, but the best friend I have ever had in my entire life. Jack O’Leary and I first met over 25 years ago at what else? But an REO Conference of course. Jack was one of those truly rare people in this world that always gave better then he got. And yes – those of you who knew Jack well – also know what I mean by that - in that it went both ways. Jack was always there for me and always had my back no matter what the situation was, no matter what the problem was – Jack was always there. But it was not just for me – Jack was there for all of us over the years. I do not think there is anyone ever in this or any other family that has ever done more for so many than Jack. Jack gave of himself and his time without reservation and more importantly - without judgment. Over the past two decades Jack helped more members than anyone. He was the first person you called when you had a problem and he was always the first one there to help. I cannot even begin to count the number of lives he has impacted and the businesses and even careers that Jack has saved. Jack was always the one you called when you got yourself into a jam, and there was no one better at helping you get out of it. That was Jack’s God-given talent. He had a way about him and as many of our members can attest, he would not only take the time to listen to your problems and give advice- but damnit – he gave the best advice! Somehow, he had a way of putting it all into perspective and then coming up with the realistic solution. I could not even begin to count how many of our members still have their business and their careers because of Jack. I cannot even begin to count the number of members whose life Jack helped change for the better. His support and guidance have given many a lifestyle that they never would have had on their own. More importantly - not all his help and advice were always business related. Over the years I watched Jack help many others through their own family tragedies and personal crises as well. No matter what the problem – Jack would always be there, and he would always be able to help. – That was Jack! My favorite aspect of Jack was obviously Jack himself. He was truly one of a kind and one of the smartest and wisest men I have ever known. But what made Jack totally unique and truly special was his ability wrap that wisdom in humor. Whatever the problem – even if it was of your own making, Jack found a way to educate, inspire, and sometimes even chastise you, all while keeping you laughing. No matter what the problem or issue was – after five minutes talking with Jack – things just got better. Jack’s humor and wit were legendary not just in our group but through the entire industry. As Jack was battling this round of cancer, I had been speaking with him almost every day. Even with everything that he was going through, radiation, surgery, chemo – he was still more worried about all of you – his “NRBA Family” than he was about himself. He actually felt bad that he was not in a position to contribute and keep helping everyone the way he once had. Go figure – but this was Jack, and that was how he felt. Jack wanted me to let everyone know that all of you were like family to him and that he loved each and everyone one of the NRBA members and that being a part of this group and loved by so many really made him feel that his life had meaning. Even though it was always Jack helping everyone else in our group – It was Jack that felt grateful. Again – this was Jack! Jack was also probably the funniest human being that I have ever known. I cannot even begin to count the times that we had to stop a meeting or even a conversation because we were all laughing so hard that we were unable to continue. Yes, he could use humor to tear someone apart in an instant. But he also had the ability lift that person up at the same time. It was a rare gift. Jack kept his sense of humor all through this and just recently after apologizing for not being able to be on the NRBA webinar. – Yes - I know – Jack is battling terminal cancer and he is apologizing for missing a webinar… this is how dedicated he was to all of you! He gave the reason that he did not want anybody to be freaked out by having to watch the (in his words): “the world’s ugliest Make-A-Wish kid” give a speech…. Again – this was Jack. All of you are exceptionally good about letting me think that I am somehow the leader of this group – But the hard reality of it is that Jack O’Leary was the true “Heart and Soul” of the NRBA. Jack was truly “one of a kind” and absolutely irreplaceable. Jack, you will be missed!

J Sarcia of East Freetown wrote:

Jack would give you his last sip of water stranded in a desert. He was so giving to me and my family during the lowest hardest times we had. I will miss him.

Pat Owen of Brea, CA wrote:

Jack was always willing to share his expertise, past experiences and humor with me... or anyone in his circle for that matter. I enjoyed every minute of conversation that I ever had with him and would look forward to seeing him at any event that I attended. I'm so sad that I haven't seen him since last year thanks to this damn Covid. Rest well, my friend... you are deeply missed.

Maureen Hunte, NRBA of Boston, MA wrote:

My deepest sympathies Eileen. Jack was so special to me and my Mom. (May she also rest in peace) My mom trusted Jack to watch over me during our NRBA travels which meant she found him to be as special and unique as I. He is missed and forever held deeply in my heart. Thank you for sharing him with me and the NRBA family! I will always be there for you, whatever you need, so please don't forget that! xoxoxo

David Supinger of Farmington, UT wrote:

After the end of an NRBA conference I was sitting alone having dinner. Im not super outgoing. Jack came up, asked how I was doing and sat down and just talked with me. Then when Mike Krein and the NRBA leaders came in he invited me to go sit with them. I got to know some of them because of Jack. Later at all the future conferences Jack would say hi and then we'd just talk about life and family; not real estate. My favorite was when Jack talked about his tow truck days and his experiences working with the police. Jack was tough as nails but had a soft heart. The kind of man I aspire to be.

sally koss of Millis wrote:

Jack was a strategic thinker with a generous heart. Told great stories and kept everybody laughing. Never too busy for YOU . . . always had time to chat. Jack was unique and one of a kind.. . Truly a caring, loving and genuine person. He was a gift to all who knew him and will be deeply missed.

Kathleen Festino of Toms River, NJ wrote:

Jack was an amazing man, we came to know each other through business 11 years ago. Through the years I always admired all the wealth of information he shared with his NRBA family, and he made us all laugh and remember the guidance he was giving. He will be greatly missed by so many. My deepest sympathy and thoughts are with all the family and friends that adored this man we his NRBA family did!