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Caldwell & Co. Established

Caldwell Trust Company already had its roots when Roland Caldwell formalized his consulting services by establishing Caldwell & Co., an advisory firm specializing in investment guidance for the trust industry. 

Late 1980s

Roland Caldwell begins the Investment Newsletter

Roland Caldwell had become known as the author of a respected investment newsletter and was also a trust consultant for a major bank in Venice, Florida. 


Kelly and Roland Caldwell_1988_Original Office in Venice_201 Center RoadKelly Caldwell Joins Caldwell & Co.

Kelly Caldwell, a recent high-honors engineering graduate of Georgia Institute of Technology, found Caldwell & Co. so interesting that he abandoned plans for law school and joined Roland at Caldwell & Co.


wwbCaldwell Trust Company was Founded and Mission Statement Written

Roland and Kelly called on respected associates to help prepare the charter application for what would become one of the few independent trust companies in Florida. Roland then wrote "What We Believe" and the charter process began.


Charter_CTCNov. 2, 1993: Caldwell Trust Company Receives Charter








Nov. 3, 1993: Caldwell Trust Company serviced its first client. We're proud to say that many of our original clients, and their families, are still with Caldwell Trust Company today.


Roland Caldwell_Around 1993_Original Office in Venice on_201 Center RoadJan. 3, 1994: Caldwell Trust Company moves into its offices in Venice on 201 Center Road 

original boardMar. 1, 1994: Caldwell Trust Company's original Board is formed 


newspaperApr. 22, 1996: Sarasota Herald-Tribune features Caldwell Trust Company in Business Weekly, The House Roland Built



l-gabbert-jamesOct. 1, 2001: James S. Gabbert joins the Caldwell Trust Company Board of Directors 

l-kraut-maryDec. 1, 2001: MaryAnn C. Caldwell-Kraut joins the Caldwell Trust Company Board of Directors


l-thacker-leeApr. 1, 2006: H. Lee Thacker, who started as a client in 1996, joins the Caldwell Trust Company Board of Directors

JimWoodsnocropweb-2Apr. 15, 2006: James R. Woods joins the Caldwell Trust Company Board of Directors  


                                    Nov. 3, 2009: Caldwell Trust Company Celebrates 15 Years Anniversary  CTC Anniversary_15


l-caldwell-kellyApr. 1, 2009: Kelly Caldwell Named to Leadership Florida Class of XXVIII


KathleenToalenocropweb (1)Apr. 15, 2009: Kathleen Toale Joins Caldwell Trust Company Board of Directors

Sarasota Office_1561 Main Street_InteriorJune 1, 2009: Caldwell Trust Company opens office in downtown Sarasota in June of 2009, 1561 Main Street 

Nov. 1, 2009: Caldwell Trust Company named first-place winner as "Best Investment Company" by Venice Herald-Tribune 


Dec. 1, 2009: John S. Booth, III joins the Caldwell Trust Company Board of Directors  

MargaretMaistonocropweb-2 May 1, 2010: Margaret Maisto Joins Board of Directors


ChristopherN.GraywebOct. 1, 2010: Christopher N. Gray Joins Board of Directors



lee hackerDec. 1, 2010: Boys & Girls Club Honor H. Lee Thacker as Maytag Man




SKY AcademyFeb. 1, 2012: Caldwell Trust Company Pledges $10,000 to SKY Academy for New Computers for Students


Florida Center_Corp Partner of The Year Award 2012Sept. 4, 2012: The Florida Center Selects Caldwell Trust Company as Corporate Partner of the Year. 


IMG_2309-1-887670-edited Sept. 1, 2013: Halfacre Construction Company Partners With Caldwell Trust Company and Breaks Ground for New Headquarters in Venice 

Mavella-0041Sept. 1, 2013: Greater Sarasota Chamber of Commerce recognizes Caldwell Trust Company with Investing in the Future and Attaining Milestone Anniversary (20th Anniversary). 




markOct. 1, 2013: Mack Reid Joins Caldwell Trust Company Board of Directors


Edrise L  Sievers-1-026824-editedNov. 1, 2013: Edrise Seivers Celebrates 20 Years at Caldwell Trust Company


dannyNov. 5, 2013: Danny Williams Celebrates 20 Years with Caldwell Trust Company


Nov. 5, 2013: Caldwell Trust Company Recognized by Sarasota County Commissioners for 20 Years of Professional Services, Community Giving and Employment Opportunities and Continues to Grow



ctc 20


Nov. 20, 2013: Caldwell Trust Company Celebrates 20th Year Anniversary


Dec. 1, 2013: Since the year 2000, Caldwell Trust Company has increased community contributions by 500%


l-gabbert-jamesJan. 1, 2014: Jim Gabbert appointed to Chair of Review Board

Gov. Rick Scott appoints Jim Gabbert, Chair to the Sarasota County Charter Review Board.

All Winner Group_Outside 2014July 1, 2014: Caldwell Trust Company Named Large Business of the Year

Venice Area Chamber of Commerce names Caldwell Trust Company as 2014 Large Business of the Year.


Timeline_Blog-090862-editedSept. 1, 2014: Caldwell's financial advisers present up-to-the-minute information with new blog www.blog.ctrust.com

corporate headquartersDec. 1, 2014:  New Corporate Headquarters In Venice Are Completed!



ThomasStuhleynocropwebNov. 1, 2015:  Tom Stuhley joins Caldwell Trust Company Board of Directors



ctcDec. 1, 2015: Tramm Hudson joins Caldwell Trust Company Board of Directors




l-thacker-leeJan. 1, 2017: H. Lee Thacker celebrates 20 years


SBA-2017WINNERSmallBiz_duoJune 1, 2017: Caldwell Trust Company Wins Small Business of the Year Award from Greater Sarasota Chamber of Commerce


SBA-2017WINNERProfessional_duoJune 1, 2017: Caldwell Trust Company Wins Professional Services of the Year Award from Greater Sarasota Chamber of Commerce



suzanne thackerJan. 1, 2018: Suzanne Thacker Celebrates 20 Years





Jan. 1, 2018: Caldwell Trust Company Celebrates 25th Year Anniversary 


IMG_3447 (1)March 1, 2018: Sheryl Vieira and Caldwell Trust Win ADDY for Excellence in Advertising
Capture2May 1, 2018: Florida Trend recognizes Caldwell Trust Company as Top Trust Banking Firm for 2018






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