Wills vs. Trusts: The Estate Planning World Series

Many of our nights and weekends over the past few months have been spent at the baseball field. My son has taken a love for the game and is constantly asking me how fast I think his fastball is, or if he might get to pitch in his upcoming game. Although I don’t always know the answers to his questions, it did cause me to think of an analogy in the world of estate planning.

My clients will often ask, “What is better, a Will or a Trust? So today, I will outline the fundamentals using baseball analogies. My sincere apologies if you don’t know much about baseball, but I think you will get the point.

First Inning: Game Time

Will

The Will doesn’t even step onto the field until the final inning—after you’re gone. Then it lumbers into probate court, where the judge acts as umpire and everything gets reviewed, debated, and—yes—delayed.

Trust

The Trust? It’s a starter. It’s playing from day one. Whether you’re healthy, injured, or off the field entirely, it keeps the game moving without court interference. It handles your lineup, signals the plays, and avoids the probate dugout.

Score: Trust leads 1–0

Second Inning: Home Field Advantage

Will

When the Will hits the field, the stadium lights go on. Everything’s public—assets, debts, beneficiaries. The fans (and curious in-laws) get a full play-by-play.

Trust

The Trust plays a private game. It’s like a spring training match—no press, no grandstands, no leaks. It protects your family’s privacy and avoids extra innings in court.

Score: Trust up 2–0

Third Inning: Handling Injuries

Will

If you’re incapacitated, the Will’s still in the locker room. It only comes out after death. Until then, it’s no help with managing bills, assets, or decisions.

Trust

The Trust? It’s a utility player. If you’re sidelined, it seamlessly steps up to bat, handling your finances without calling in a judge or fanfare.

Score: Trust pulls ahead 3–0

Fourth Inning: Setup and Salary Cap

Will

Wills are easy to draft, quick to sign, and budget-friendly. Think of it as a rookie contract. But probate fees and delays later can rack up costs fast.

Trust

Trusts require more effort and upfront investment—you have to title assets correctly, update accounts, and keep it maintained. But in the long run? Lower fees, less hassle, and smoother gameplay.

Score: Will sneaks in a run. 3–1

Fifth Inning: Managing the Roster

Will

Wills work like a single-season manager: they outline who gets what, but don’t control how or when. If your 19-year-old inherits a fortune, they get it all at once—Ferrari, anyone?

Trust

Trusts let you set the rules of the game. You can distribute in stages, protect assets from creditors, or provide for special needs—think of it as a strategic playbook for generations.

Score: Trust steals another base. 4–1

Final Inning: The Tie-Up

Wills and Trusts are both valuable teammates in your estate planning lineup. Wills are great for simple estates, naming guardians, and basic transfers. But Trusts offer privacy, flexibility, and long-term control—especially for more complex family or financial situations.

Final Score: Trust Wins 5–1

But here’s the twist: smart estate planning uses both. The Will handles anything left off the field (called a “pour-over” Will), while the Trust makes the major plays.

So, whether you’re coaching a small team or a dynasty, the best game plan is one that’s personalized, strategic, and keeps your loved ones from getting caught in a legal rundown.

Matt Bushman, JD