Member-only session

Could CRA Be Keeping the Stanley Cup Out of Canada?

Live date December 2025
Live time 12:00 p.m. – 1:30 p.m. ET
Duration 90 minutes

Session starts in:

--
days
--
hours
--
mins
--
secs

This session is included with your CTM membership.

Canadian autumn forest

See what to expect

⏱

Live session + Q&A

105 minutes of teaching plus 15 minutes of live Q&A discussion.

▶

Recording access

The webinar recording will be available shortly following the live event.

☷

Detailed slide deck

Includes tax tables, worked examples, planning notes, technical references, and supporting resource materials.

✓

CPD certificate

A CPD certificate is available after successful quiz completion.

Real-world planning question

When does a signing bonus stop being an inducement to sign?

John Tavares's seven-year, US$77 million contract put roughly 92 per cent of its value into signing bonus — US$15.25 million in the first year against US$650,000 of base salary. CRA argues that amounts which are conditional and repayable if the player does not perform are remuneration for services rather than an inducement to sign, which would mean the treaty cap never engages at all. No authority supplies a positive test for what makes a payment an inducement, so the answer turns on the terms of the agreements and the surrounding circumstances.

What we'll work through

01

The Reassessment and What Is Actually in Dispute

  • Non-resident status when the first-year signing bonus was received
  • What was reported on the Canadian and the United States return
  • Character of the payment under challenge, not disclosure
  • Timeline from the 2018 payment to the August 2026 hearing
02

Two Rules, in Order: Canadian Law Then the Treaty

  • Where a non-resident's Canadian employment-income exposure comes from
  • ITA ss. 2(3)(a), 115(1)(a)(i), and the signing-bonus provision
  • Article XVI(4) in its own words, and its four operative features
  • Why the paragraph 4 cap reaches athletes and nobody else
  • Reciprocity: the same rule with the two countries reversed
03

What Fifteen Per Cent Caps, and What It Does Not

  • A ceiling on one country's taxing right, not a rate of tax
  • Residence-country taxation and the foreign tax credit interaction
  • United States state taxes that may not follow the treaty
  • Why the combined total lands near the higher of the two rates
04

CRA's Two Planks and the Khabibulin Problem

  • Conditionality and repayment as indicators of remuneration
  • Magnitude and tranche structure across the full contract term
  • Khabibulin and Curran on finding a payment's true character
  • A characterization dispute with no allegation of sham
  • The absence of any positive test for "inducement"
05

If the Cap Never Engages

  • Measuring the portion attributable to duties performed in Canada
  • Whether a home-games proxy actually measures Canadian duties
  • CRA's administrative starting point, and its limits as authority
  • Protective claims to keep the United States year open
06

Why the Structure Exists, and What a CRA Win Costs

  • Cash flow, time value, and protection through a work stoppage
  • Repayment clauses that cut in both directions
  • Top combined rates across Canadian and NHL-hosting US markets
  • A chilling effect on the structure before any rule changes
  • Whether Article XVI(4) still has a place in the treaty

The bigger tax questions behind the Tavares case

The facts involve an NHL contract and the Canada–U.S. tax treaty. But the case raises much broader questions about characterization, contractual wording, CRA’s interpretation of the law, and what happens when reasonable positions collide.

Characterization Changes Everything

Tax results can turn on what a payment actually is—not simply what the parties call it. The Tavares case shows how the characterization of the same payment can produce very different tax consequences.

CRA’s Position Is Not the Final Word

CRA’s interpretation matters, but it is not the law. This case shows why understanding the reasoning behind CRA’s position can matter just as much as knowing the position itself.

Cases Build Better Tax Judgment

You may never advise an NHL player. But unusual cases expose principles that routine files can hide—and sharpen the judgment needed when the answer is not obvious.

Learn with Kim and Jay

Kim G C Moody

Tax Authority

Kim G C Moody

LinkedIn

FCPA, FCA, TEP

  • Former Chair, CBA/CPA Joint Committee
  • Former Chair, Canadian Tax Foundation
  • Parliamentary committee witness
Jay Goodis

TAX STRATEGY & OPTIMIZATION

Jay Goodis

LinkedIn

CPA, CA

  • CPA Ontario Emerging Leader
  • Parliamentary committee witness
  • National tax & keynote speaker

Questions before joining?

Yes. CTM memberships can be purchased for a team or firm, with per-user pricing based on the number of members. See Team & Firm pricing.

You'll receive a confirmation email for your registration, along with a link to access the live session.

If you cannot attend live, the recording will be made available in your CTM account shortly after the session ends, so you can watch on demand.

Yes. The detailed slide deck and supporting materials will be posted shortly before the live session. When the recording is available, you'll be notified by email.

You can access this session and its materials through your CTM account for as long as your CTM membership is active.

Yes. A CPD certificate is available after successful quiz completion.

Yes. We will take questions during the live Q&A portion after the teaching session.

No. CTM members don't need to register for live sessions. We'll email you the link to join automatically. If you don't see it, check your spam folder or contact us.

Ready to register

This session is included with your CTM membership, along with the full member library.

Questions about this course?