Jack Osteraas

WAUNAKEE/MADISON - Jack Francis Osteraas, founder of Operation Fresh Start, Madison police officer, Picnic Point park ranger, State of Wisconsin budget analyst, and all around good guy, passed away peacefully in his sleep on Monday, April 22, 2019 after a weekend of visits from family and friends. At heart, Jack was a small town guy from Willmar, Minnesota (born 1935 to David Quam Osteraas and Frances Elizabeth Victoria (Nelson) Osteraas), graduating from Willmar High School in 1954, and then off to Wausau, Wisconsin in 1958 with his family: wife Dorothy Lee (Wetherby) Osteraas and children John David, Jana Lee, and Mark Jordan. Jack fell in love with the zaniness of the Mad Town after moving here in 1966. The mid-60s saw Jack in uniform with the Madison Police department, followed by two idyllic years at Picnic Point as the park ranger (does anybody remember the caretaker's cottage?). At the dawn of the 70s Jack was working as a juvenile detention counselor and saw first-hand the need for a program to help at-risk youth find their way in life. Operation Fresh Start (OFS) was born at his home office desk in 1970! Jack nurtured OFS in its early days and it has blossomed and matured in the years since. With his background as a sales guy (shoes, bread, then meat) he had the wonderful gift of conversation and making people feel comfortable, which was perfect for fundraising for a non-profit. OFS was by far his proudest professional legacy. After OFS Jack spent a few years as the administrative officer with the Middleton Police Department, and the rest of his career with the State of Wisconsin as a budget analyst, retiring in 1997.

In 1986 Jack met Jean White Martin, a happy and vibrant school teacher from DeForest who brought joy to Jack's life. With Jeannie's two young boys, Steven and David, a new family emerged with wedding vows in 1988. Together Jack and Jeannie enjoyed the outdoors and camping, in the early years braving the storms in a tent, then graduating to a pop-up trailer and finally going all the way with a monster truck and a camper trailer. After the (not so) rough camping life, travel continued around the United States, Mexico and Europe, often with grandchildren along for the adventure. They retired to a little cabin in the big woods of central Wisconsin until 2010 when the lure of Madison and family brought them back "home".

Jack had a life-long passion for home projects - repairs, remodeling, painting, tinkering, woodworking (toy boxes for grandkids seemed to bring him the most joy), you name it he could do it, on a (self-imposed) slim budget and making it work with what he had. He was a patient teacher of craftsmanship to his sons, step-sons and grandchildren, who carry on the tradition.

And, of course, this story is not complete without mentioning the Packers and the Badgers. Jack was an avid but fair-weather Packer fan - but only after they fired Bart Starr and only if they were winning (comfortably). The same with Badger football, which he enjoyed when they were winning, even holding season tickets until the UW started extorting donations to go along with ticket prices (Jack, after all, was frugal, and he would be happy to know that we are getting the maximum word count for the obituary fee).

Daughter Jana tragically died in a traffic accident in 1976, first-wife Dorothy in 1990, and infant son Michael in 1956. Still around to enjoy many happy years with Jack are wife Jeannie, sons John and Mark, step-sons Steven Martin (Jenny) and David Martin (Katie), twin brother Jerome (Jerry) Osteraas (Carol), sister A. Jean Osteraas, and grandchildren Nick Osteraas (Aline), Sarah Osteraas, Jacob Boyes, Jacob Martin, Katelyn Osteraas, Krista Osteraas, Devin Hunter, Braylon Martin and former wife and good friend Eleanor "Lelu" Tyrrell.

Friends are invited to a celebration of Jack's life at Operation Fresh Start, 2670 Milwaukee St, Madison, WI 53704, on Saturday, May 18, 2019, from 2:00pm to 4:00pm, with an open mic at 3:00pm to share stories of Jack and how he touched their lives. You may also share your best memories of Jack on the Cress Funeral Service website, cressfuneralservice.com. Jack always loved a good joke and a good story, so don't hold back.

In lieu of flowers, memorials may be made to Operation Fresh Start (operationfreshstart.org) or Agrace Hospice.


Winn-Cress Funeral Home
5785 Hwy Q
Waunakee, WI 53597
608-849-4513