Here’s a Look at the Best Investments to Hold in a TFSA – and Why
Image via Deposit Photos
We recently had a question from a member of Pat McKeough’s Inner Circle that asked:
“Pat, I hold Intel in a non-registered account with a capital loss showing and am thinking of transferring it to my TFSA “in kind” with no tax penalty. Is Intel a suitable stock to hold in a TFSA?”
We’re not tax experts, so you might want to consider talking to an expert, especially if there are large funds involved.
However, transferring shares in kind into a TFSA does trigger a capital gain or loss for income tax purposes.
If the investment is in a capital gains position, you will have to declare it as a capital gain on your income tax return. But if there is a capital loss, you will not be able to declare the loss for tax purposes. This is because the government still sees you as the beneficial owner of the security.
Note that if you sell the shares in a non-registered account, you can deduct your loss against capital gains. For example, if he were to sell his Intel shares in 2023, he’d get to deduct the loss against his 2023 capital gains.
If you still have capital losses left over, you can carry them back up to three years (2022, 2021 and 2020), or forward indefinitely to offset future capital gains.
Hold Lower-Risk Investments in a TFSA
We think it is best to hold lower-risk investments (such as blue-chip stocks we see as buys like Intel) in your TFSA. That’s because you don’t want to suffer big losses in these accounts. If you do, you can’t use those losses to offset capital gains, as is the case with taxable (non-registered) accounts. You’ll also lose the main advantage of a TFSA: sheltering gains from tax. You won’t have gains to shelter if the value of your investments falls. Continue Reading…
John Tavares of the Toronto Maple Leafs is in a dispute with the Canada Revenue Agency that could impact pro athletes and high-income earners in general.
Financial advisor Darren Coleman, a cross-border expert, discussed the Tavares case in a recent episode of the podcast: Two Way Traffic. His guests were tax lawyer Shlomi Levy and tax accountant Kevyn Nightingale of Levy Salis LLP. The firm, which has NHL players as clients, is dedicated to U.S. and Canadian tax and estate planning for individuals, corporations, and those with cross-border interests.
In 2018 Tavares, then a US resident, left the New York Islanders to sign a seven-year, $77-million (US) contract with the Maple Leafs. For the first year of that contract his base salary was $650,000 (taxed in Canada at 53%) with $15.3 million a signing bonus (taxed in Canada at 15%). But now the CRA says that was all salary and wants back taxes. With penalties that comes to about $8 million US.
“The CRA says it was all employment income,” said Nightingale and his colleague Levy explained what a CRA win might mean. “It would make it harder for Canadian NHL teams to compete with American teams in lower-tax jurisdictions. But it goes beyond that.”
Today I’m joined by my good friends, Kevin Nightingale and Shlomi Levy of Levy Salis LLP. Kevin is one of the top cross-border tax accountants and Shlomi one of the top cross-border tax attorneys in North America.
We’re going to talk about the John Tavares case and his tax issues with CRA. It’s getting a lot of press and attention. Tavares of the Toronto Maple Leafs is a hometown boy and it was a big deal in July 2018 when he went into free agency and signed with the Maple Leafs a seven-year contract that would have paid him $77 million [US] and $15 million of that was an upfront signing bonus.
Six years later, CRA wants millions of dollars of unpaid taxes because of the way the deal was structured. This can have an impact on how NHL teams recruit and could apply to every sports team, but also in the corporate world when trying to bring talent to Canada. I know you guys have players as clients but do not represent Mr. Tavares.
Kevyn Nightingale
The main issue is it’s expensive to get athletes to come to Canada. The tax difference between Canada and the U.S. is wide and has been widening over years, especially since 2015 when the then new Liberal government decided to raise tax rates, particularly on high earners, and they were thinking of your home-grown high earners. But in a world where talent is mobile, particularly in things like sport, if you raise tax rates you lower their effective income and what they care about is the after-tax income.
Compare coming to play for the Toronto Maple Leafs, where tax rates are 53.5% on the vast majority of their income, and going to Florida where the tax rate is 37%. That makes a big difference. Now there are other states where there are significant taxes. California is getting close and New York City is getting close, but there are ways of dealing with that in the US that still make the tax rate effectively lower for many players.
Darren Coleman
So the structuring of the Tavares contract was trying to give him some tax benefit by structuring a signing bonus vs. a salary. Shlomi, can you dig into why that mattered?
Shlomi Levy
Shlomi Levy
Tax paid in the state of New York isn’t credited against the Canadian side, but is based on the Canada-US tax treaty and the potential tax savings were probably $1.3 million. But now, if CRA gets its way between penalties and interest six years down the road, it would be probably three or four times that amount in payment.
So you have to question the strategy. One of the things I like to discuss with clients and athletes is what’s the risk and what is the reward vs. the risk? You want to make sure people take those calculated risks. God knows how long this may take to settle and it might just not be worth it. I represent north of 50 NHL players come training camp and these guys can’t be bothered with legal discussions or tax discussions. They’re focused on playing hockey. This is going to be a huge distraction for John and his family if it doesn’t get settled quickly.
Kevyn Nightingale
He only had to pay Canadian tax of 15% on the signing bonus portion that he received prior to coming to Canada.
Darren Coleman
So I think his assumption was he was not a resident of Canada. I think that’s what CRA is challenging.
Kevyn Nightingale
He was by all accounts a non-resident of Canada because he was living in New York and playing for the Islanders, and had not yet come to Canada when he got this portion of the signing bonus. Now he ultimately did move to Canada, but that was after the fact. So we’re only talking about the part that he received prior to coming to Canada. The deal is if you have a signing bonus and it’s properly authorized as a signing bonus, and you’re a non-resident of Canada and it’s paid by a Canadian team, your Canadian tax goes down from 53.5% to 15% so that is a sizeable savings. As a resident of the US he has to pay US tax on his worldwide income. And he’s paying US tax, and he’s paying New York state tax because he lives in New York state. Now he will get a credit for the Canadian 15% but he’s still paying effectively US and New York rates that may go as high as 45% or even more. So Shlomi is right. The savings are about a million dollars.
Darren Coleman
The difference between the tax rate and what the Canadian tax rate would have been?
Kevyn Nightingale
Yes, he would have been ahead of the game, but not by a huge amount. It’s not like someone who’s living in Texas or Florida, which many athletes do. But CRA says we don’t care what the US aspect is. We lost the difference between 53.5 and 15. That’s what we care about.
Darren Coleman
You mentioned earlier it’s the characterization of a signing bonus. Is that also part of what CRA is saying? That it wasn’t a signing bonus? You received it as income?
Kevyn Nightingale
CRA is arguing that it’s really employment income but you call it a signing bonus. We’re still going to call it employment income. One of the factors that goes into it is whether the employee, in this case, the athlete, has to repay any of it if he doesn’t actually show up to work. So, injured, retired, not feeling like working that kind of stuff. Well, apparently that is not at issue here because if Tavares did not show, he would not get the signing bonus. So that argument is a loser for CRA because they just don’t have the facts on their side.
Shlomi Levy
The nature of the NHL contract is you signed a contract that’s guaranteed and you’re owed the money.
Darren Coleman
Where do you think CRA has ground to stand on this one?
Kevyn Nightingale
CRA is saying it’s just so big compared to everything else. The signing bonus in total is $70 million, almost $71 million and that cannot not be employment income. 71 million of the 77 million has to be employment income and that’s it.
Darren Coleman
How does this affect how you negotiate or how you talk to players about this?
Shlomi Levy
Until there’s a judgment on this, it definitely puts people on their back feet. I want to say only the first 15 million of the signing bonus is being contested here because the following bonuses were paid to him as a Canadian citizen and tax resident. So it’s not really contested. The bulk of the work I’ve done is mostly with Canadian athletes who are resident here. So we haven’t had any of these issues. We do deal with a lot of Canadian athletes who married American girls, so the complexity is still there, but I would say that a lot of free agents, especially when it comes to baseball, and even the CFL in Toronto, are going to be looking at this carefully.
Darren Coleman
Because as a group they have more Americans moving to Canada than hockey players, right?
Shlomi Levy
Correct. Look at Toronto. You’ve got Austin Matthews, who’s an American citizen and he’ll probably straddle that line. He’s never considered a Canadian tax resident. You’ve got some Europeans with Nylander in Toronto as well. Big contract, big signing bonuses. So a lot of people are going to be watching this, and the strategy for Canadian teams might change significantly depending on what this judgment produces.
Darren Coleman
I think fans are watching this because the tax thing can really affect the fortunes of how teams are going to be able to produce. Because if they can’t, if they’ve got such a huge tax hurdle, how are we ever going to recruit top talent if this is an issue?
Kevyn Nightingale
It is an impediment to hiring people, to doing business anywhere if you don’t know what the answer is going to be.
Shlomi Levy
In the US your individual tax rates at the federal level are low, and if you’re lucky enough to play in a state like Florida or Texas where there is no state tax, your maximum tax exposure is 37%. Now assume these guys are all making over a million bucks, so 37% versus 53.5%. There was an issue a few years ago in a Canadian team where a player was negotiating as an unrestricted free agent and ended up signing the same numerical deal, but one season less, with Dallas vs. the Canadian team, and everybody went up in uproars.
The argument is very simple. He was going to make net the same amount of money playing one year less. Agents and players are a lot more sophisticated. There’s a lot more that goes into negotiations, and not just the numerical value. 100 million in Montreal or Toronto is easily 85 million in the US, and add to that life, weather, taxes and probably paying less for the same amount of net money. At the end of the day, these athletes are phenomenal individuals. They’re well-tuned machines, but they also have an expiration date on their career, and they’re trying to optimize it.
Kevyn Nightingale
This is something many governments have trouble coming to terms with, and that is there are limits to tax. And this is the thin edge of the wedge, where you see at the top end, the talent is mobile. And you can’t just say, well, we’re going to raise their tax rates from 45% to 55% and we’re going to get 10 extra points. No. People respond. People respond to incentives.
And if you tell them you’re going to pay that much more here, they’ll say, I’ll go somewhere else where I can do better on a net basis. And that is not just the NHL and NBA and football and basketball and baseball. It is every sport, but it’s also more importantly in business. Business is more and more global, and employment is more and more global at the top end. Major Canadian corporations are hiring a CEO. They’re not just looking at Canada. They’re looking to the US as well. If you’re a new potential CEO coming up from the States you say, Well, I understand your taxes are that much higher. Pay me that much more if you want me. That makes the Canadian company much less competitive.
Darren Coleman
You run into a problem. One, it’s hard to recruit people in the lower-tax jurisdiction to come to our higher-tax jurisdiction. And then we have the way Canadians are taxed. I want to get into this because a lot of people don’t know this nuance. It’s easier for Canadians to leave our tax system. So we not only have trouble recruiting brainpower, but we also can lose talent and brainpower. It’s surprising to me how many people are surprised by this and it’s the difference between how Americans are taxed, which is on citizenship, and Canadians are taxed on residency.
Shlomi Levy
I want to go back to a statement made a bit earlier that one of the other big concerns we should have as Canadians is the attitude of our current government just grabbing as much as they can get. You look at the way the treaty works, and very often there’s a bit of IOU, you know, Canada to the US and US to Canada. It all works on an IOU system and it worked just fine until this current government came and started piling up all kinds of new catches and new grabs to make it much more difficult.
And the recent legislation they pushed forward about businesses and foreign affiliates doing business and foreign tax credits going up and down and the imposition it wishes to impose on dividends from a foreign affiliate and an extra 22% in Canada, and then one day issue a credit on extractions of dividends from that company. These are cash grabs that are telling a guy sitting in his office thinking about expansion to the US and thinking that he’s going to use corporate money and get that taxed like an individual. Next thing you know he says I’m not going to do it. And it takes away from our ability to expand our business and ideas into the US. Our Canadian government just wants to tax the jitters out of us. Continue Reading…
My latest MoneySense Retired Money column looks at a variety of tax and savings limits changes that are effective early in 2025. Click on the highlighted headline for the full column: What retirees need to know about tax brackets for 2025.
As the column notes, at or near Retirement taxes and inflation are the two big threats to preserving enough wealth to last a lifetime. The tax burden hits home with the annual tax-filing deadline in April, but the time to start thinking about the yearly ordeal is before year-end.
The complexity of this task is compounded by almost-annual changes to tax brackets, the Basic Personal Amount, OAS thresholds, inflation adjustments and much more. For starters, I recommend reading an excellent article by CIBC Wealth’s tax guru, Jamie Golombek, which appeared in the Financial Post here on Nov. 23rd, shortly after the Canada Revenue Agency released its new tax numbers for the year 2025.
Let’s look first at inflation, the second serious scourge retirees face if they live long enough. Here, a useful tool suggested by certified financial planner Morgan Ulmer is Statistics Canada’s Personal Inflation Calculator, which lets you compare your personal inflation rate to the general CPI.
Ulmer, of Toronto-based Caring for Clients, sees the higher tax brackets and inflation adjustments as an “opportunity for retirees to build a savings reserve.” CPP is indexed to inflation yearly while OAS is indexed quarterly. So “if a retiree is able to increase their spending at a rate that is less than CPI, the difference could be saved as an emergency reserve or invested in a TFSA.”
Inflation and Tax Bracket changes
Back to some key data cited by Jamie Golombek. The inflation rate used to index 2025 tax brackets and amounts will be 2.7%: just over half the 4.7% in effect in 2024. The good news is that the Basic Personal Amount (BPA) on which no federal tax is levied rises to $16,129 in 2025: It was $15,000 in 2023.
All five federal income tax brackets are indexed to that 2.7% inflation rate. In 2025, the bottom federal tax bracket of 15% will apply to incomes between zero and $57,375. The second lowest bracket of 20.5% will apply to incomes between $57,375 and $114,750. The 26% bracket applies to income between $114,750 and $177,882, while incomes between $177,882 and $253,414 will attract a 29% federal tax. After that the federal rate will kick in at 33%.
Below is a table summarizing that information prepared for MoneySense:
MoneySense.ca
Don’t forget there will be additional provincial taxes on top of the federal haul, also indexed to inflation at various provincial rates.
What is relevant for those in the Retirement zone is the higher threshold on Old Age Security: in 2025, according to Canada.ca, OAS begins to get clawed back for taxable income of $90,997. OAS benefits disappear entirely at $148,451 for those aged 65-74 in 2025, and at $154,196 for those 75 or over. Note the OAS clawback is based on individual incomes, not household income.
Deferring CPP and OAS till 70
Matthew Ardrey, portfolio manager and Senior Financial Planner for Toronto-based TriDelta Financial, agrees that tax brackets, whether federal or provincial, “become more of a consideration in retirement.” For many Canadians receiving employment income on a T-4, there is little we can do as retirees to keep income in the lower tax brackets. But there’s plenty to think about when considering tax minimization and decumulation strategies. Referring to Golombek’s article, Ardrey says that using federal brackets only, taxpayers can receive $57,375 of income and pay very low rates of taxation, especially when the $16,129 basic personal amount is considered.”
Retirees under age 70 can defer CPP and OAS until 70 and try to live on withdrawals from their registered plans instead. With no other income, taxpayers could have almost $50,000 of after-tax income, or $100,000 for tax-paying couples. Continue Reading…
Solo entrepreneurs face unique financial challenges, including inconsistent income streams, high operational costs, limited access to capital and the difficulty of separating personal and business finances. Effective financial planning becomes crucial to navigating these hurdles and ensuring sustainable business operations and long-term success.
Creating realistic budgets, building emergency funds and managing expenses allows solo entrepreneurs to stabilize their financial health. Additionally, seeking professional financial advice offers personalized strategies, tax planning and investment guidance, which are essential for securing a stable and prosperous future.
Unique financial hurdles for Solo Entrepreneurs
Variable revenue presents significant challenges for solo entrepreneurs in budgeting and managing expenses. The unpredictable nature of income makes it difficult to plan for consistent cash flow, often leading to financial strain. According to a recent survey, 77% of respondents reported their expenses increased by 6% or more due to inflation, further complicating financial planning.
Solo entrepreneurs also face the challenge of managing overhead costs without the benefit of economies of scale. Unlike larger businesses that can reduce per-unit costs through bulk purchasing, they must find ways to cover operational expenses efficiently. In fact, 37% of small businesses resort to borrowing to meet their operating expenses, which highlights the financial pressure they endure.
Securing loans and investments is another hurdle for solo entrepreneurs. Financial institutions and investors may view them as high-risk due to their lack of a proven track record and limited collateral. This makes it difficult for single proprietors to obtain the necessary funding to grow and sustain their businesses. Continue Reading…
Small businesses play a sizeable role in shaping Canada’s economy, contributing significantly to national employment numbers and our country’s gross domestic product (GDP).
According to Statistics Canada, in 2022 businesses with 1 to 99 employees made up 98 per cent of all employer businesses in this country. But today’s economic environment has triggered new financial challenges for this cohort. Canadian entrepreneurs can help offset the cost of rising inflation, rising cost of inputs, and rising interest rates, and keep more money in their pockets, by adopting some or all of these key tax strategies.
Consider employing your immediate family
Income splitting, whereby the higher-earner transfers part of their income to a lower-earning family member, can reduce the tax owed by your household. Consider paying a reasonable salary to your spouse and/or children for the services they provide for your business to reduce your tax obligations.
Incorporate your business
If your business generates more profit than you need to live on, incorporation is a highly effective tax strategy. It could lead to a significant tax deferral by qualifying for the lower small business tax rate for active income – the longer the profits are left in the company, the larger the tax deferral. If shares of the business are ultimately sold and are eligible for the lifetime capital gains exemption, the tax deferral gained through incorporation can create a permanent tax saving.
Other potential advantages of incorporation include having family members own shares (so as to have access to multiple capital gains exemptions) and possibly paying out dividends to actively participating family members who are taxed at a lower rate.
Maximize tax breaks with registered plans
Consider your RRSP contribution room when setting and reporting remuneration for services provided by yourself and family members who also work in the business. Employment income creates RRSP contribution room for the following year which, for 2024, can represent up to $31,560 of room. RRSP contributions are tax deductible, provide tax deferral and allow for business owners to diversify their future retirement income. Contributing to a tax-free savings account (TFSA) can also work in your favor by allowing you to withdraw funds if needed without penalty. Continue Reading…
Posted By 
Posted By 
Posted By 
