Dana Olson

Head Coach Milford Boys Basketball / Assistant Coach Milford Football

[Dana Olson @Coacholson2]

Keep grinding 🏈🦅❤️

[Dana Olson @Coacholson2]

Keep grinding 🏈🦅❤️

[Dana Olson @Coacholson2]

🦅🏈

[Kyle Grabowski @kylegrbwsk]

‘Anything can happen on draft week’ for Milford’s Brady Olson after a record-setting season at Central Connecticut and diligent preparation https://t.co/XTw7J5SSvS

[Dana Olson @Coacholson2]

Patriots' Efton Chism III Works Out With Local QB Prospect https://t.co/CeFhVFF9l8

[Dana Olson @Coacholson2]

https://t.co/OrIuSIpvu7

[Dana Olson @Coacholson2]

Keep grinding 🏈

[Dana Olson @Coacholson2]

🏀🦅

[Matheus.Dasilvva @MatheusDasilvva]

Junior szn highlights @Coacholson2 ⁦@CoachERiley⁩ https://t.co/TojzKFFRkH

[Dana Olson @Coacholson2]

🦅🏈 https://t.co/H1ti1dHZab

[Dana Olson @Coacholson2]

https://t.co/2WF06MxfvM

[Dana Olson @Coacholson2]

🦅❤️

[Mike Rittelmann @MRittCGS]

🏈 2026 @CGSAllStar Player Profile

QB @Brady_Olson_241
📍 @CCSUfootball

📏 Measurements
• Height: 6’3 3/8”
• Weight: 210 lbs
• Hand: 9 5/8”
• Arm: 31 1/2”
• Wingspan: 77”

📊 2025 Season Stats
• 3,132 passing yards | 25 TDs
• 140 rushing yards | 3 TDs

🏆 Honors & Highlights
✅ 1st Team All-@NECFootball
✅ School record: 423 passing yards in a single game

#AllStarSeasonStartsWithCGS

[Dana Olson @Coacholson2]

🦅🏈

[Adam Lechtenberg @CoachLecht]

✌️time champions & 3 highly decorated ⁦@ccsu_fb⁩ players earning opportunities to compete at the next level. ⁦@TheDreamBowl⁩ ⁦@CGSAllStar⁩ Best of luck to our guys this weekend! @IsaiahD4074⁩ ⁦@Brady_Olson_241⁩ ⁦@e_izzy03⁩ ⁦⁦⁦⁦

[Dana Olson @Coacholson2]

Go vote 🦅🏀 Matt had a special night 🏀🦅

[Kyle Grabowski @kylegrbwsk]

Vote for our 1st winter @MetroWestSports boys athlete of the week https://t.co/1SYk6KwkA7 @BVTBeavers @HillerAthletics @Warriors978 @HMhockeyteam @NatickAthletics @KTBroncoball @medwaypuck @HHSHawksAD @Gonksports @WaylandWrestlin

[Dana Olson @Coacholson2]

Good Win and a monster night for our junior guard 🦅🏀

[Ryan Lanigan @R_Lanigan]

Final: Milford 97, Burncoat 81. Junior Matt DaSilva drops a career-high 51 points (‼️) 5 reb 3 ast 3 stl, junior Manny Vilbrun career-high 26 pts, Ryan Burns 11 reb 5 pts 4 ast, Jason Stokes 14 reb 9 ast 3 stl. Jaiden Johnston 33 pts for Burncoat. #hockomock

[Dana Olson @Coacholson2]

👍

[Greg Berge @GregBerge]

Why Coaching Is Harder Than People Think (A Holiday Reminder)…

Because coaching isn’t just about plays, drills, or game nights.

It’s about people.

It’s about walking into practice every day and managing emotions you didn’t create but are responsible for.

Your own.
Your players.
Your assistants.
Parents.
Administrators.
Fans.

It’s about teaching kids who are all at different stages.

Different maturity levels.
Different confidence levels.
Different home situations.

And somehow holding them to the same standards while still meeting them where they are.

It’s about decisions that look simple from the stands but feel heavy from the sideline.

Who plays.
When.
Why.
How you communicate it.

And how that decision might land on a 16-year-old who ties their identity to minutes.

It’s about losing sleep over kids who won’t buy in.

Over conversations you need to have.

Over mistakes you replay in your head long after everyone else moved on.

It’s about being judged by people who see the outcome, not the process.

The scoreboard, not the hours.

The result, not the relationships.

And yet, you show up again.

You plan. You teach. You model. You care.

As the season slows and the holidays arrive, this is the reminder:

What you do matters.

Even when it goes unseen.
Even when it feels heavy.
Even when it’s hard.

Coaching is about influence. And influence lasts longer than any season.

That’s why coaching is harder than people think. And also why it matters so much.

As the year winds down, I hope you find a little rest, a little perspective, and a lot of pride in the work you’re doing.

🎄Happy Holidays, Coach.

[Dana Olson @Coacholson2]

Truth 🙏

[Greg Berge @GregBerge]

The 10 Truths Parents Rarely See

1. Coaches lose sleep.
2. Decisions aren’t personal.
3. Playing time is complex.
4. Culture matters more than stats.
5. Accountability is care.
6. Coaches invest emotionally.
7. Development isn’t instant.
8. Hard feedback is intentional.
9. Wins don’t tell the whole story.
10. Coaches remember kids forever.

Perspective matters.

[Dana Olson @Coacholson2]

❤️🏈

[Caleb Gelsomino @Coach_Gel]

Impossible to capture everything @Brady_Olson_241 has meant to this team over the last two years. Thank you for all you invested into @ccsu_fb , congratulations on a record breaking season. Looking forward to watching what comes next 👀!!🐐🐐🐐

[Dana Olson @Coacholson2]

Congrats nephew 🏈

[NEC @NECsports]

🏈🥇 The 2025 All-NEC Football First Team (Offense)

#NECFB x #NECelite

[Dana Olson @Coacholson2]

Brady Olson Interview https://t.co/shADai9hZJ via @YouTube

🏈🦅

[Dana Olson @Coacholson2]

@Brady_Olson_241 threw all the struggles you kept your head down and just kept grinding. We are all so
Proud of you congrats champ 🏈

[Rob @RobGNBH]

Your 2025 NEC football champions. #NECFB

[Dana Olson @Coacholson2]

@BostonHeraldHS Met Bruce back when I was 14 playing AAU basketball. We went to Vegas for Nationals . Bruce was one of the fiercest competitors I played with and against . RIP