In connection with our investing and operating activities, we have entered into certain contractual obligations and commitments. See Note 8 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, 2023 were as follows (in millions):


	Payments Due by Period
Contractual Obligations	2023			2024			2025			2026			2027			Thereafter			Total
Senior Notes	$	—		$	—		$	—		$	—		$	—		$	3,550.0		$	3,550.0
Note purchase agreements		425.0			200.0			640.0			478.0			200.0			2,005.0			3,948.0
Credit Agreement		245.0			—			—			—			—			—			245.0
Premium Financing Debt Facility		289.0			—			—			—			—			—			289.0
Interest on debt		311.9			317.9			299.1			280.6			261.3			3,374.8			4,845.6
Total debt obligations		1,270.9			517.9			939.1			758.6			461.3			8,929.8			12,877.6
Operating lease obligations		108.9			100.4			84.0			67.6			50.6			81.8			493.3
Less sublease arrangements		(2.4	)		(1.8	)		(1.7	)		(1.6	)		(1.1	)		(0.8	)		(9.4	)
Outstanding purchase obligations		116.5			59.0			24.9			20.2			15.0			47.1			282.7
Total contractual obligations	$	1,493.9		$	675.5		$	1,046.3		$	844.8		$	525.8		$	9,057.9		$	13,644.2

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 can accommodate approximately 2,000 employees. 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 $50.0 million and $80.0 million over a fifteen‑year period. We have earned approximately $51.3 million of EDGE credits from inception in 2017 through December 31, 2023.

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 $183.5 million in 2023, $176.6 million in 2022 and $153.4 million in 2021.

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, 2023. 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, 2023 were as follows (in millions):


													Total
	Amount of Commitment Expiration by Period												Amounts
Off-Balance Sheet Commitments	2024		2025		2026		2027		2028		Thereafter		Committed
Letters of credit	$	—	$	—	$	—	$	—	$	—	$	21.2	$	21.2
Financial guarantees		2.0		0.2		0.1		0.1		—		—		2.4
Total commitments	$	2.0	$	0.2	$	0.1	$	0.1	$	—	$	21.2	$	23.6

Since commitments may expire unused, the amounts presented in the table above do not necessarily reflect our actual future cash funding requirements. See the Off-Balance Sheet Debt section below for a discussion of 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 2020 to 2023 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 $2,009.8 million, of which $1,294.2 million was recorded in our consolidated balance sheet as of December 31, 2023 based on the estimated fair value of the expected future payments to be made, of which approximately $564.8 million can be settled in cash or stock at our option and $729.4 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, 2023 and 2022 that was recourse to us.

At December 31, 2023, we had posted two letters of credit totaling $9.3 million in the aggregate, related to our self-insurance deductibles, for which we had a recorded liability of $13.7 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, 2023, we had posted nine letters of credit totaling $10.5 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 one letter of credit totaling $0.5 million as security deposits for a 2015 acquisition’s lease. 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, 2023 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 2024

None

None

—

—

         Trigger - Agreed conditions met

        Other

Credit support under letters of credit (LOC) for
   deductibles due by us on our own insurance
   coverages - expires after 2028

None

None

9.3

13.7

        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 2024 and 2028

None

Reimbursement of LOC fees

10.5

—

        Trigger - Dissolution or catastrophic financial
   results of the operation

Collateral related to claims funds held in a fiduciary
   capacity by a recent acquisition - expires 2028

None

None

0.9

—

        Trigger - Claim payments are not made

Credit support under letters of credit in lieu of security
   deposits for one lease from acquisitions - expires after 2028

None

None

0.5

—

        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

0.6

—

        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

None

1.8

—

        Trigger - Default on loan payments

23.6

13.7

(1)

The guarantees are collateralized by shares in minority holdings of our Canadian operating companies.

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 routinely are involved in legal proceedings, claims, disputes, regulatory matters and governmental inspections or investigations arising in the ordinary course of or incidental to our business, including relating to E&O claims and those noted below in this section. We record accruals in the consolidated financial statements for pending litigation when we determine that an unfavorable outcome is probable and the amount of the loss can be reasonably estimated. For the matters we disclose that do not include an estimate of the amount of loss or range of losses, such an estimate is not possible or is immaterial, and we may be unable to estimate the possible loss or range of losses that could potentially result from the application of non-monetary remedies, unless disclosed below. We currently believe that the ultimate outcome of these proceedings, individually and in the aggregate, will not materially harm our financial position, results of operations or cash flows. However, legal proceedings and government investigations are subject to inherent uncertainties, and unfavorable rulings or other adverse events could occur, including the payment of substantial monetary damages or an injunction or other order prohibiting us from selling one or more products at all or in particular ways, precluding particular business practices or requiring other remedies, which may result in a material adverse impact on our business, results of operations or financial position.

During 2022, we received a subpoena from the FCPA Unit of the U.S. Department of Justice seeking information related to our insurance business with public entities in Ecuador. During the fourth quarter of 2023, the DOJ informed us that it had closed its inquiry and would not be pursuing enforcement action against us in connection with this matter.

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 indirectly infringed patents held exclusively by Midwest Energy and sought unspecified damages and injunctive relief. During fourth quarter of 2023, we settled this matter for an amount that was not material and without admitting any wrongdoing.

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.

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 $10.0 million between $100.0 million and $225.0 million, and up to another $20.0 million between $225.0 million and $400.0 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, 2023 consolidated balance sheet is above the lower end of the most recently determined actuarial range by $6.7 million and below the upper end of the actuarial range by $6.9 million. 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, 2023, we had exposure on $108.0 million of previously earned tax credits. Under the Tax Cuts and Jobs Act (which we refer to as 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, 2023 consolidated balance sheet related to this exposure.