Steal My Tax Season Playbook

👋 Welcome back to Sponcon Sports, a weekly newsletter dedicated to sponsored content strategy in the sports industry! 

Mac McClung isn’t defending his dunk contest crown, and a shoe insert brand broke the news.

That’s not an accident.

Team VKTRY and Mac McClung have been partnered since 2023, and it’s been a natural fit from day one. VKTRY sells carbon-fiber insoles designed to increase bounce and explosiveness. McClung? A three-time defending NBA Dunk Contest champion. Product benefit meets cultural proof.

They’ve leaned into that connection before (h/t Jason Bergman), activating around All-Star Weekend and the dunk contest in past years. But this year, they went bigger.

Instead of waiting for the contest, VKTRY used a creator partnership with Cheyne Gitsham to deliver the biggest scoop of All-Star Weekend: McClung won’t go for a fourth-straight win in 2026. The video reveal racked up 4.2M across channels, instantly positioning VKTRY at the center of the dunk contest conversation, without needing official league access.

And they didn’t stop at breaking the news.

VKTRY is using that moment to pull fans back to their own channel. On February 14 at 10pm, immediately after the dunk contest, McClung will exclusively reveal the dunks he had prepared on VKTRY’s Instagram. The timing is intentional. It capitalizes on peak attention and invites the inevitable debate: Would he have won again?

When timing, talent, and distribution align, a brand can shape the conversation instead of reacting to it. Breaking news is powerful. Owning the follow-up is what turns attention into a lasting brand win.

In Today’s Edition:

• Tax Season Sponcon Upgrades 📂

• Winter Wins In Foxborough ❄️

• 433’s Goldin Opportunity 🪙

🏊️ DEEP DIVE
The Smart Way To Sponsor Tax Season

Every year, tax season triggers one of the biggest advertising blitzes in sports.

From New Year’s through Tax Day, brands like TurboTax and H&R Block flood the market with media spend—heavy on logo slaps, heavier on reminders, all designed to win the moment when consumers finally sit down to file.

But awareness alone doesn’t build preference.

This week, I was inspired by two TaxAct reads on The Bill Simmons Podcast, “We Kept The Receipts” and “Great Returns.” They worked because each made a clean, memorable connection between the content and the job the brand helps you do.

That’s the unlock for this category.

Tax brands don’t just need more impressions, they need mental availability when the purchase decision happens. And they don’t need to disappear after April 15th either. With the right framing, taxes, numbers, transactions, and adjustments are already baked into sports year-round.

So below is my playbook: ideas I’d pitch to consumer financial services brands that want to build equity during tax season, and stay relevant long after it ends.

Content Platforms & Storytelling Series

We Kept The Receipts

NFL teams love posting graphics after a win showing every pundit who picked against them. From a league and media perspective, you can revisit past moments between players, like this example from House Of Highlights.

This is a perfect sponsorship fit. Pair those high-performing posts with a “We Kept The Receipts presented by Brand” lockup for maximum impact. The challenge is you never know how many of these can be done during the season, so it can be used as added value to get a deal over the line.

Extension: Ask players for preseason predictions, then revisit them at season’s end. Formula 1 runs this format with drivers on YouTube and generated nearly 900K views. Add a “We Kept The Receipts” brand lockup on the cards players read from to make the integration feel native and repeatable.

Why it works: Receipts are a core mental cue for filing taxes. This reinforces brand relevance through sports storytelling, not interruption.

Great Returns

Ahead of drafts, playoffs, or major matchups, look back at decisions that paid off.

This can include:

• Draft picks that exceeded expectations

• Smart in-game decisions broken down by players, coaches, or analysts

• In tennis, simple highlight packages featuring literal “great returns”

Brand everything as “Great Returns, presented by Brand.”

Why it works:
“Returns” directly maps to tax refunds while also celebrating smart decision-making, positioning the brand as a partner in outcomes, not paperwork.

Know Your Numbers

Filing taxes is all about knowing your numbers, so turn that insight into content.

Create a short-form series quizzing players, coaches, or alumni on:

• Their own career stats

• Iconic team numbers

• Fan-favorite trivia moments

For fans, add surprise-and-delight prizing for diehards who ace the quiz. Compile the episodes into a longer YouTube video at season’s end, similar to how the NBA packages social content into long-form.

Why it works: It makes numbers entertaining while reinforcing the idea that being informed, and prepared, pays off.

My First Million

Recreate GQ Sports’ My First Million with an added financial twist.

Have players share:

• Contract length and earnings that got them to their first million

• A graphic breakdown showing how much went to taxes

• What they learned about money early in their career

Why it works: It’s aspirational, educational, and honest—three things financial brands struggle to balance. This format builds trust without preaching.

Transactions, Rules & How It Works Content

Transactions Platform (Always-On)

Instead of one-off sponsorships, attach the brand to all transaction announcements: signings, extensions, trades, and waivers.

This becomes a year-round platform, not a seasonal buy. Click here to get my How To Sell Team Transactions playbook.

Why it works: It keeps the brand relevant 12 months a year, even when taxes aren’t top of mind.

Extension: At the league or media level, let the brand sponsor reaction content when transactions happen. Think what Bobby Marks does for ESPN and its NBA coverage.

Each clip includes:

• Salary cap or luxury tax implications

• Roster impact

• A recurring “Compliance Check” segment covering rules, cap space, and constraints

Why it works: Fans already care about transactions, this makes the brand the guide to understanding the fine print.

Can You Run A Sports Team? (Interactive Quiz)

Over the summer, the Financial Times launched a Premier League management game where fans act as CEO, balancing financial and operational decisions.

Bring the brand into the experience with logo placement throughout the game and in-question integration. For example: “You’re speaking with your TurboTax luxury tax expert—what’s your next move?”

Why it works: Fans get hands-on with financial decision-making, making the brand an active partner in strategy and planning. It’s a fun, memorable way to connect taxes and numbers to the sports experience, and the interactive format drives engagement that lasts well beyond tax season.

Cap & Taxes 101

For fans who love the details, launch an email drip course explaining salary caps and luxury taxes. You could even have the current, or former GM contribute to it.

The brand presents the series, with integrated ad space and a clickable logo. End the “course” with a virtual meet-and-greet featuring a GM or commissioner.

Why it works: Education builds credibility, and credibility matters when consumers are choosing who to trust with their money.

Financial Expert AMA

Give fans access to the team’s ultimate financial decision-maker: the GM.

Host a Reddit AMA where fans ask about:

• Trades

• Cap strategy

• What it’s like managing a franchise’s finances

Film the session for YouTube or let a brand expert interview the GM for the brand’s owned channels.

Why it works: It humanizes financial expertise and positions the brand alongside trusted leadership.

Graphics, Stats & In-Game Moments

Crunch The Numbers

A clean, flexible name for stat graphics before, during, or after games.

Why it works: Simple, repeatable, and brand-safe, perfect for consistent exposure.

File It Away

Use for pregame stat graphics showing historical advantages or matchup dominance.

Also works for head-to-head “tale of the tape” visuals.

Why it works: Filing is reframed as preparation, not paperwork.

Filed Under W

Postgame highlight reels or photo albums from wins stamped “Filed Under W.”

Why it works: Celebrates wins while reinforcing filing language in a positive context.

Pregame Audit

Another take on matchup graphics: “Tale of the Tape, Audited by Brand.”

Why it works: “Audit” sounds official and credible, exactly how tax brands want to feel.

Postgame Box Score, Itemized

Sponsor postgame box scores posted after wins but Instead of “presented by,” brand the graphic with “Itemized by Brand.”

Why it works: Turns a standard asset into a clever brand moment fans won’t gloss over.

Halftime Adjustments

Sponsor a halftime segment focused on in-game adjustments or retrospective (pregame) breakdowns of moments that changed outcomes.

Why it works: Direct parallel between tax adjustments and strategic decision-making.

Runs / Goals / Points Withheld

Sponsor defensive highlights that prevented scoring.

Why it works: “Withheld” is a subtle tax cue that feels organic in sports.

Hockey Penalty Integration

Sponsor opponent penalty boxes with signage reading “Avoid Costly Penalties” or brand penalty kills as “Penalty Kills, supported by Brand.”

Why it works: Clear behavioral parallel without forcing tax language.

Tax Break (In-Game Feature)

During timeouts, run a “Tax Break” segment: trivia, mini-games, or quick savings tips on the video board.

Why it works: Short, fun, and interactive, with a clever tie back to filing taxes.

Ticketing, Promos, & Fan Value

Receipts Sweepstakes

Add a QR code to all concession receipts for a sweepstakes entry.

Winner announced late in the game to encourage fans to stay. This ties receipts to data capture and increased spend.

Why it works: Receipts are reframed as rewards, not chores.

Tax Day Ticket Offers

Price tickets at $4.15 or $41.50 on or near April 15th.

Why it works: Simple, clever, and extremely shareable.

Fee-Free Homestand / Fridays

Eliminate fees for a full homestand or recurring Fee-Free Fridays, with creative that literally crosses fees out.

Add a B2B angle: premium buyers get “withheld fees” rebated as F&B or upgrades.

Why it works: Consumers hate fees. Brands that remove friction win goodwill.

Tax Day Theme Night

Have the brand present an entire game on, or near April 15th. If you work in the NHL or NBA, this could be your Fan Appreciation Day.

Layer in:

• BOGOs

• Credits

• “Refund”-style giveaways

Why it works: Turns a stressful date into a positive fan experience.

Trigger Promotions (Refunds)

If the team wins on Tax Day, fans receive a partial “refund” as team cash for merchandise or concessions.

This mechanic works any time when framed correctly. Sponcon Sports sponsor, Cheers Cash, can power it.

Why it works: Gamifies refunds without touching real money.

Filing Credit

When fans file through the partner platform, offer exclusive ticket deals or merchandise inside the refund flow.

Rates should be unavailable elsewhere and feel like true steals.

Why it works: Connects filing directly to joy and entertainment.

In-Person Tax Filing Support

For one day, turn your venue into a tax filing center with free help from the brand.

Set up desks on the field, in clubs, or suites for a unique visual and community impact.

Why it works: Blends service, trust, and local goodwill, everything tax brands want more of.

🔍️ SPONCONSPIRATION
Steal These Ideas

When the New England Patriots clinched a Super Bowl berth during a nationwide blizzard, Ariens, an outdoor power equipment brand, was ready. The “King of Snow” literally cleared a path for the AFC Champions as they returned to Foxborough from their win in Denver. Perfect timing meets perfect product placement.

433’s Career In Collectibles series is a smart format because it taps into nostalgia, reliving legendary careers through collectibles as the storytelling hook. It’s a perfect fit for sponsor Goldin, where the caliber of athlete aligns directly with their high-end collectibles business.

Want to add extra brand value when filming inside your venue? Use digital signage. The Chicago Bulls did exactly that for State Farm in an episode of Stanchion to Stanchion featuring Derrick Rose. This placement also could’ve been a natural fit for Kia, whose logo already lives on the stanchion pad at the United Center.

During the Barcelona Shakedown, the Mercedes F1 team shared daily debriefs via voice notes, exclusively in their WhatsApp channel. Those notes consistently ranked among the top-performing pieces of content in terms of engagement. WhatsApp even used a comment to DM CTA on Instagram to drive people to the channel.

When a new player or coach joins your team, the auto category should always be in play for sponsored content. The Tennessee Titans nailed this by picking up new head coach Robert Saleh in a Nissan, and tagging the brand directly in the copy.

🚨 ICYMI
What To Watch For

Cricket Meets Creators: Team USA T20 World Cup matches will be available for free on the Jomboy Media’s YouTube channel, where they’ll be leading a creator-led telecast [via Courtney Hirsch].

War Room Wins: Jazmin Griffith shared a step-by-step guide for running a successful Super Bowl war room whether your brand is in the game or watching from the sideline [via What The Data Said newsletter].

OOH That Travels: Jordan Rogers broke down why out-of-home works so well as social content, rounding up his top five sports ads on The Sphere. Big screens, built-in virality, and visuals designed to travel online.

Ad Math, Explained: RO CEO Zach Reitano delivered a sharp breakdown of the economics behind a Super Bowl ad, why the financial risk is often misunderstood, and how RO plans to measure success beyond the spot itself.

Cleats Meet Controllers: adidas is bringing its Predator vs. F50 rivalry to their Twitch channel today (2pm ET) with Team Predator vs. Team F50, a 10v10 EA Sports FC Clubs showdown hosted by gaming creator Morgan Burtwistle (@angryginge13).

Haute In Hoops: Balenciaga’s NBA collaboration has officially entered the digital world via NBA 2K26. Fans can now outfit their MyPlayer with coach jackets, oversized tees, tracksuits, and zip-up hoodies, bringing luxury fashion straight into gameplay.