In connection with our investing and operating activities, we have entered into certain contractual obligations and commitments. See Notes 8 and 14 to these consolidated financial statements for additional discussion of these obligations and commitments. Our future minimum cash payments, including interest, associated with our contractual obligations pursuant to the Senior Notes, Note purchase agreements, Credit Agreement, Premium Financing Debt Facility, operating leases and purchase commitments at December 31, 2021 were as follows (in millions):

	Payments Due by Period
Contractual Obligations	2022			2023			2024			2025			2026			Thereafter			Total
Senior Notes	$	—		$	—		$	—		$	—		$	—		$	1,600.0		$	1,600.0
Note purchase agreements		200.0			250.0			475.0			200.0			640.0			2,683.0			4,448.0
Credit Agreement		45.0			—			—			—			—			—			45.0
Premium Financing Debt Facility		228.4			—			—			—			—			—			228.4
Interest on debt		236.5			229.0			212.3			197.7			178.8			1,568.5			2,622.8
Total debt obligations		709.9			479.0			687.3			397.7			818.8			5,851.5			8,944.2
Operating lease obligations		101.6			94.5			67.9			51.4			39.0			77.3			431.7
Less sublease arrangements		(0.8	)		(0.6	)		(0.3	)		(0.3	)		(0.2	)		(0.3	)		(2.5	)
Outstanding purchase obligations		71.5			60.7			38.1			30.4			11.2			26.2			238.1
Total contractual obligations	$	882.2		$	633.6		$	793.0		$	479.2		$	868.8		$	5,954.7		$	9,611.5

The amounts presented in the table above may not necessarily reflect our actual future cash funding requirements, because the actual timing of the future payments made may vary from the stated contractual obligation.

Senior Notes, Note Purchase Agreements, Credit Agreement and Premium Financing Debt Facility - See Note 8 to these consolidated financial statements for a summary the amounts outstanding under the Senior Notes, Note purchase agreements, the Credit Agreement and Premium Financing Debt Facility.

Operating Lease Obligations - Our corporate segment’s executive offices and certain subsidiary and branch facilities of our brokerage and risk management segments are located in a building we own at 2850 Golf Road, Rolling Meadows, Illinois, where we have approximately 360,000 square feet of space and will accommodate approximately 2,000 employees at peak pre-pandemic capacity. Relating to the development of our corporate headquarters, we expect to receive property tax related credits under a tax-increment financing note from Rolling Meadows and an Illinois state Economic Development for a Growing Economy (which we refer to as EDGE) tax credit. Incentives from these two programs could total between $60.0 million and $90.0 million over a fifteen-year period. We have earned approximately $32.6 million of EDGE credits from inception in 2017 through December 31, 2021.

We generally operate in leased premises at our other locations. Certain of these leases have options permitting renewals for additional periods. In addition to minimum fixed rentals, a number of leases contain annual escalation clauses which are generally related to increases in an inflation index.

Total rent expense, including rent relating to cancelable leases and leases with initial terms of less than one year, amounted to $153.4 million in 2021, $154.0 million in 2020 and $148.1 million in 2019.

We have leased certain office space to several non-affiliated tenants under operating sublease arrangements. In the normal course of business, we expect that certain of these leases will not be renewed or replaced. We adjust charges for real estate taxes and common area maintenance annually based on actual expenses, and we recognize the related revenues in the year in which the expenses are incurred. These amounts are not included in the minimum future rentals to be received in the contractual obligations table above.

Outstanding Purchase Obligations - We typically do not have a material amount of outstanding purchase obligations at any point in time. The amount disclosed in the contractual obligations table above represents the aggregate amount of unrecorded purchase obligations that we had outstanding at December 31, 2021. These obligations represent agreements to purchase goods or services that were executed in the normal course of business.

Off-Balance Sheet Commitments - Our total unrecorded commitments associated with outstanding letters of credit, financial guarantees and funding commitments at December 31, 2021 were as follows (in millions):

													Total
	Amount of Commitment Expiration by Period												Amounts
Off-Balance Sheet Commitments	2022		2023		2024		2025		2026		Thereafter		Committed
Letters of credit	$	—	$	—	$	—	$	—	$	—	$	17.0	$	17.0
Financial guarantees		1.3		1.4		2.0		0.2		0.1		0.1		5.1
Funding commitments		0.5		—		—		—		—		—		0.5
Total commitments	$	1.8	$	1.4	$	2.0	$	0.2	$	0.1	$	17.1	$	22.6

Since commitments may expire unused, the amounts presented in the table above do not necessarily reflect our actual future cash funding requirements. See Note 14 to these consolidated financial statements for a discussion of our funding commitments related to our corporate segment and the Off-Balance Sheet Debt section below for a discussion of other letters of credit. All of the letters of credit represent multiple year commitments that have annual, automatic renewing provisions and are classified by the latest commitment date.

Substantially all of the purchase agreements related to these acquisitions we do contain provisions for potential earnout obligations. For all of our acquisitions made in the period from 2017 to 2021 that contain potential earnout obligations, such obligations are measured at fair value as of the acquisition date and are included on that basis in the recorded purchase price consideration for the respective acquisition. The amounts recorded as earnout payables are primarily based upon estimated future potential operating results of the acquired entities over a two- to three-year period subsequent to the acquisition date. The aggregate amount of the maximum earnout obligations related to these acquisitions was $1,873.9 million, of which $988.5 million was recorded in our consolidated balance sheet as of December 31, 2021 based on the estimated fair value of the expected future payments to be made, of which approximately $670.3 million can be settled in cash or stock at our option and $318.2 million must be settled in cash.

Off-Balance Sheet Debt - Our unconsolidated investment portfolio includes investments in enterprises where our ownership interest is between 1% and 50%, in which management has determined that our level of influence and economic interest is not sufficient to require consolidation. As a result, these investments are accounted for under the equity method. None of these unconsolidated investments had any outstanding debt at December 31, 2021 and 2020 that was recourse to us.

At December 31, 2021, we had posted two letters of credit totaling $9.4 million in the aggregate, related to our self-insurance deductibles, for which we had a recorded liability of $18.3 million. We have an equity investment in a rent-a-captive facility, which we use as a placement facility for certain of our insurance brokerage operations. At December 31, 2021, we had posted eight letters of credit totaling $6.1 million to allow certain of our captive operations to meet minimum statutory surplus requirements plus additional collateral related to premium and claim funds held in a fiduciary capacity, one letter of credit totaling $0.9 million for collateral related to claim funds held in a fiduciary capacity by a recent acquisition, and two letter of credit totaling $0.6 million as security deposits for leases from acquisitions. These letters of credit have never been drawn upon.

Our commitments associated with outstanding letters of credit, financial guarantees and funding commitments at December 31, 2021 were as follows (all dollar amounts in table are in millions):

Description, Purpose and Trigger

Collateral

Compensation

to Us

Maximum

Exposure

Liability

Recorded

Other investments

Funding commitment to an equity investment -

to be funded in 2022

None

0.5

—

Trigger - Agreed conditions met

Other

Credit support under letters of credit (LOC) for

deductibles due by us on our own insurance

coverages - expires after 2026

None

9.4

18.3

Trigger - We do not reimburse the insurance

companies for deductibles the insurance companies

advance on our behalf

Credit enhancement under letters of credit for our

captive insurance operations to meet minimum

statutory capital requirements - expires after 2026

None

Reimbursement of LOC fees

6.1

—

Trigger - Dissolution or catastrophic financial

results of the operation

Collateral related to claims funds held in a fiduciary

capacity by a recent acquisition - expires 2022

None

0.9

—

Trigger - Claim payments are not made

Credit support under letters of credit in lieu of security

deposits for two leases from acquisitions - expires after

2023 and 2026

None

0.6

—

Trigger - Lease payments do not get made

Financial guarantees of loans to 5 Canadian-based

employees - expires when loan balances are reduced

to zero through May 2029 - Principal and interest

are paid quarterly

(1)

None

1.0

—

Trigger - Default on loan payments

Financial guarantee of external loan to subsidiary in

Chile - expires when loan balance is reduced to

zero through July 2024 - Principal and interest are

paid quarterly

None

4.1

—

Trigger - Default on loan payments

22.6

18.3

Since commitments may expire unused, the amounts presented in the table above do not necessarily reflect our actual future cash funding requirements.

Litigation, Regulatory and Taxation Matters - We are a defendant in various legal actions incidental to the nature of our business including but not limited to matters related to employment practices, alleged breaches of non-compete or other restrictive covenants, theft of trade secrets, breaches of fiduciary duties and related causes of action. We are also periodically the subject of inquiries, investigations and reviews by regulatory and taxing authorities into various matters related to our business, including our operational, compliance and finance functions. Neither the outcomes of these matters nor their effect upon our business, financial condition or results of operations can be determined at this time.

In July 2019, Midwest Energy Emissions Corp. and MES Inc. (which we refer to together as Midwest Energy) filed a patent infringement lawsuit in the United States District Court for the District of Delaware against us, Chem‑Mod LLC and numerous other related and unrelated parties. The complaint alleges that the named defendants infringe patents held exclusively by Midwest Energy and seeks unspecified damages and injunctive relief. The case is in discovery. We continue to defend this matter vigorously. Litigation is inherently uncertain and it is not possible for us to predict the ultimate outcome of this matter and the financial impact to us. We believe the probability of a material loss is remote.

As previously disclosed, our IRC 831(b) (or “micro-captive”) advisory services businesses has been under audit by the IRS since 2013. Among other matters, the IRS is investigating whether we have been acting as a tax shelter promoter in connection with these operations. Additionally, the IRS is conducting a criminal investigation related to IRC 831(b) micro-captive underwriting enterprises. We have been advised that we are not a target of the criminal investigation. We are fully cooperating with both matters. We are not able to reasonably estimate the ultimate amount of any potential loss in connection with these matters, we do not expect any loss to be material to our consolidated financial statements.

Contingent Liabilities - We purchase insurance to provide protection from errors and omissions (which we refer to as E&O) claims that may arise during the ordinary course of business. Currently we retain the first $15.0 million of every E&O claim up to $15.0 million. In addition, we retain, in aggregate: up to another $2.0 million between $15.0 million and $100.0 million, plus up to another $20.0 million between $100.0 million and $225.0 million, and up to another $10.0 million between $225.0 million and $365.0 million. We have historically maintained self-insurance reserves for the portion of our E&O exposure that is not insured. We periodically determine a range of possible reserve levels using actuarial techniques that rely heavily on projecting historical claim data into the future. Our E&O reserve in the December 31, 2021 consolidated balance sheet is above the lower end of the most recently determined actuarial range by $3.7 million and below the upper end of the actuarial range by $5.8 million. In addition to this E&O reserve, in 2021, we established provisions for potential unusual pandemic related claim defense and other costs. We can make no assurances that the historical claim data used to project the current reserve levels will be indicative of future claim activity. Thus, the E&O reserve level and corresponding actuarial range could change in the future as more information becomes known, which could materially impact the amounts reported and disclosed herein.

Tax-advantaged Investments No Longer Held - Between 1996 and 2007, we developed and then sold portions of our ownership in various energy related investments, many of which qualified for tax credits under IRC Section 29. We recorded tax benefits in connection with our ownership in these investments. At December 31, 2021, we had exposure on $108.0 million of previously earned tax credits. Under the TCJA, a portion of these previously earned tax credits were refunded in 2019 for tax year 2018, according to a specific formula. Under the Coronavirus Act, Relief, and Economic Security Act (the CARES Act), which was passed on March 27, 2020, we accelerated the refund of all remaining credits on April 17, 2020, and the remaining credits were refunded to us in the second quarter of 2020. In 2004, 2007 and 2009, the IRS examined several of these investments and all examinations were closed without any changes being proposed by the IRS. However, any future adverse tax audits, administrative rulings or judicial decisions could disallow previously claimed tax credits.

Due to the contingent nature of this exposure and our related assessment of its likelihood, no reserve has been recorded in our December 31, 2021 consolidated balance sheet related to this exposure.